We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

The Loop Holiday Rentals

Payment Protection
Use a credit card to book with our Peace of Mind Protection.Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
More filters
All 90 Rentals in The Loop
loading...
From
$538
Per Night
1 / 32
The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (26) Make Enquiry
From
$366
Per Night
1 / 34
Payment Protection
The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (1) Make Enquiry
From
$368
Per Night
1 / 26
Payment Protection
The Loop
2 Bedrooms, 1 Bathroom, Sleeps 5
Bookings
Details Reviews (1) Make Enquiry
From
$306
Per Night
1 / 27
Payment Protection
The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (4) Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
About this property
1 KING SIZE Bed in the masteroom and 1 full size bed in the second and air-mattress available for more than 5 people 1600 square feet Sleeps 6 2 Flatscreen TVs Clean freshly-washed white sheets and white Towels waiting for you. Coffee maker now available. Private garage parking in the... View all property information
Make Enquiry
5 of 5 stars Reviewed 8 November 2014
The Condo was a great place for rest and relaxation between all the excitement we found in Chicago. Outstanding views of the Chicago skyline, great location, comfortable beds and...
5 of 5 stars Reviewed 2 August 2014
We loved the pad, the location, the view, and the city. Would go back to this spot in a heartbeat. The owner was courteous and easy to contact.
See all reviews
From
$184
Per Night
1 / 32
Payment Protection
The Loop
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (4) Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • Wheelchair access
  • Elder access
About this property
Welcome to the LEX Chicago -- far from your typical Chicago rental. The LEX offers unparalleled amenities, upscale stylish accommodations. The Space Michigan Avenue at 21st street 1BR / 1Ba 750ft Loft with Balcony w/d in unit attached garage (extra charge per night via building) Welcome... View all property information
Make Enquiry
5 of 5 stars Reviewed 6 November 2014
The apartment was great! The hosts were very easy to contact when needed. Even the neighbours were friendly. Good location, away from the busy city Central but still close enough...
5 of 5 stars Reviewed 30 October 2014
21st and Michigan, right on the bus route to go to the Downtown core and to get to the museums. Just blocks away from Chinatown. Market just across the street for meat and eggs...
See all reviews
From
$5,097
Per Month
1 / 14
The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
You'll love coming home to this amazing panoramic view of the Chicago skyline at this spacious long-term rental in River North. This two bedroom two bath is located near the intersection of Wells and Erie Streets features a balcony, wonderful kitchen, floor-to-ceiling windows, and a location in the... View all property information
Make Enquiry
From
$316
Per Night
1 / 10
Payment Protection
The Loop
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (1) Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
This 39-story Chicago hotel is across the river from Magnificent Mile shopping, six blocks from Lake Michigan, and a half-mile from the Loop's theater district and the Art Institute of Chicago. Located on the Magnificent Mile. Industry and creativity converge in Chicago, the birthplace of the... View all property information
Make Enquiry
5 of 5 stars Reviewed 3 December 2014
For downtown Chicago stay, this was fantastic...lots of room and great location! We were a walk away from anything...from Navy Pier to the beach to shopping to family museums. A...
See all reviews
From
$368
Per Night
1 / 25
Payment Protection
The Loop
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (1) Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Welcome to the PENTHOUSE at LEX Chicago – far from your typical Chicago rental. The LEX offers unparalleled amenities, upscale stylish accommodations, and floor-to-ceiling dynamic views of the Chicago skyline. This property is unlike any other in its class and the experience is definitely... View all property information
Make Enquiry
4 of 5 stars Reviewed 24 June 2014
This apartment was great and just as advertised. The view was incredible with floor to ceiling windows and a great balcony. We were able to watch the fireworks from Navy Pier and...
See all reviews
From
$287
Per Night
1 / 13
The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
This two queen room overlooks the city. The pillowtop bed and blackout drapes/curtains help ensure a restful night. The private bathroom has complimentary toiletries. Complimentary wireless Internet access keeps you connected, and the 37-inch plasma TV and iPod docking station are offered for your... View all property information
Make Enquiry
From
$306
Per Night
1 / 10
The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (5) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Internet Access
  • Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
**LOCATION **LOCATION **LOCATION! ***CAN'T BEAT IT! ***Views Views Views! Breathtaking Lake and City Views!!*** Looks Like Hawaii Up There!*** Set in the heart of Downtown Chicago, our Chicago apt is ideally placed for visitors to experience all that the city has to offer. On the doorstep of... View all property information
Make Enquiry
5 of 5 stars Reviewed 3 September 2014
We're home from our trip and back to reality! We loved your City and will definitely be back, next time could you arrange a bit better weather please!! But, as Brits we're used to...
5 of 5 stars Reviewed 23 July 2014
We booked through Steps From Everything and they were very easy to work with. The price was very reasonable and the location was great. We could walk two blocks to the Metro...
See all reviews
Get the List
From
$613
Per Night
1 / 24
Payment Protection
The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Reviews (7) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Beautiful B & B Boatel Yacht - Pier Gold offers Chicago visitors a great alternative to regular hotel stays. Located at Chicago's most sought after harbor in the heart of our city waterfront; at Burnham Harbor you will enjoy waking up at your floating waterfront boatel at our harbor with stunning... View all property information
Make Enquiry
4 of 5 stars Reviewed 31 July 2014
This was absolutely a great choice for a buddy and I to hang out in Chicago for a long weekend. The location was incredible and fortunately for so was the weather. Having done...
5 of 5 stars Reviewed 9 August 2013
A short walk (about a block) from the museums you find yourself in the quiet Burnham Harbor and on you very own Yacht! Two very private cabins, a comfortable living area with...
See all reviews
From
$386
Per Night
1 / 12
The Loop
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (9) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Hot Tub
  • Internet Access
  • Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
About this property
Walk to Everything Downtown! Enjoy Stunning Views of the City Skyline and Grant Park! ONE OF FEW 3BD/2.5BA UNITS RIGHT IN THE MIDDLE OF DOWNTOWN CHICAGO. Very affordable! ***WALK TO EVERYTHING ***YES, THESE ARE THE VIEWS! ***BREATHTAKING VIEWS OF THE CITY SKYLINE AND GRANT PARK ***3... View all property information
Make Enquiry
4 of 5 stars Reviewed 31 October 2014
This is a superb place to stay. Warm, comfortable with stunning views of downtown and Grant Park. We booked with stepstoeverything and their communications were top class...
5 of 5 stars Reviewed 19 July 2014
Pretty close to downtown parking is across the street Reservation and service are with phone communication, quick and helpful. Keyless entry Recent renovated with quality...
See all reviews
From
$386
Per Night
1 / 32
The Loop
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Reviews (2) Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
About this property
Take me to the Penthouse! Stay in our Penthouse Condo on the 50th Floor! A true Penthouse, stunning views of the lake and city. Walk to everything downtown. Upgraded everything. Granite kitchen counter tops, stainless steal appliances, marble in the bathrooms, king size beds, floor to ceiling... View all property information
Make Enquiry
5 of 5 stars Reviewed 30 June 2014
Can't sat enough good things about this place. Excellent host, great amenities, perfect location. Top shelf stay.
5 of 5 stars Reviewed 16 August 2011
Was a bit nervous booking the condo vs. a traditional hotel for a group of co-workers. Fantastic accommodations, great view, clean, convenient location. We already re-booked with...
See all reviews
From
$3,271
Per Month
1 / 40
Payment Protection
The Loop
Studio, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (6) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Gym
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
888.761.RENT or 312.242.1625 215 W. Washington St. Chicago, IL. 60606 (Washington/Wells in the Loop in Downtown Chicago - Five Blocks West of Michigan Avenue and Millenium Park 'Bean'; In Business/Theater District) Check Availability and Book Online Now: http://reservation.worldweb.com/hotel/1278... View all property information
Make Enquiry
5 of 5 stars Reviewed 19 July 2014
Beautiful furnished apartments with kitchennete and in the heart of downtown, just a few blocks away from State st and michigan ave. I had a very pleasant and comfortable stay...
5 of 5 stars Reviewed 8 May 2014
The location is so convenient, the blue line train from O'hare airport takes you right to the stop of which is about 5 minutes walk to the building. The unit is clean and with...
See all reviews
From
$165
Per Night
1 / 12
Payment Protection
The Loop
2 Bedrooms, 1 Bathroom, Sleeps 10
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Housekeeping...
  • Housekeeping...
  • Internet Access
  • Safe
  • Satellite TV
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
ADDITIONAL SPACE AVAILABLE UPON REQUEST!! Very affordable home in west suburb that offers easy access to the city. Sleeps up to 10 people. -2 Bedrooms -1 Bathroom -Hardwood Floors -Tiled Bathroom -Centrally controlled Heat and Air -Big back yard -Cable and Wireless Internet -Several... View all property information
Make Enquiry
From
$92
Per Night
1 / 18
Payment Protection
The Loop
Studio, 1 Bathroom, Sleeps 2
Booking
Details Reviews (1) Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
About this property
Studio Apartment Downtown Chicago Millennium Park; walking distance most attractions; close to public transportation View all property information
Make Enquiry
4 of 5 stars Reviewed 21 August 2014
Tr`es bien situé, propre et bien équipé. Personnel de l'immeuble bien chaleureux. Pitsfield's café `a ne pas manqué au rez-de-chaussée. Calme , bien insonorisé...`a l'exeption de...
See all reviews
From
$109
Per Night
1 / 6
The Loop
1 Bedroom, 1 Bathroom, Sleeps 3
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Sauna
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
These Vacation Rentals are located in the Chicago LOOP, a mixed-use neighborhood west of Michigan Avenue that includes apartments, homes, businesses and retailers surrounded by magnificent parks that are framed by the Chicago River to the North, Buckingham Fountain to the South, Michigan Avenue to... View all property information
Make Enquiry
4 of 5 stars Reviewed 17 September 2014
Upon arrival we were greeted with a sign on the door saying we could not use the kitchen sink. Room had no iron, dish towels, kitchen utensils, hangers, missing a light bulb in...
See all reviews
From
$184
Per Night
1 / 13
Payment Protection
The Loop
Studio, 1 Bathroom, Sleeps 3
Bookings
Details Reviews (4) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Safe
  • Satellite TV
  • Shared Indoor Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Downtown apartment with great location, views and furnishings. Large convertible studio with views of Lake Michigan and Navy Pier. Luxurious memory foam king size bed, queen size high end futon sofa, full kitchen and bath. It is a studio, so it is perfect for 2 people and a 3rd or 2 children on... View all property information
Make Enquiry
4 of 5 stars Reviewed 26 October 2014
Had great time staying here, awesome views of the lake and Navy Pier. Easily can walk to restaurants, attractions, shopping, and parks. Great place to stay.
5 of 5 stars Reviewed 1 October 2014
Very Confortable apartment. NIce neighborhood. Good location a few blocks from Millennium Park, Navy Pier and Downtown Chicago. Excellent lake view.
See all reviews
From
$1,725
Per Night
1 / 4
Payment Protection
The Loop
5 Bedrooms, 1 Bathroom, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Ocean Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
adfdfas;ldfjaskjdfaskjdfajdfajdfasjdfaskjldasf;lkjasd;flkjasld;fkjas;ldfkjlas;dfjadfdfas;ldfjaskjdfaskjdfajdfajdfasjdfaskjldasf;lkjasd;flkjasld;fkjas;ldfkjlas;dfjadfdfas;ldfjaskjdfaskjdfajdfajdfasjdfaskjldasf;lkjasd;flkjasld;fkjas;ldfkjlas;dfjadfdfas;ldfjaskjdfaskjdfajdfajdfasjdfaskjldasf;lkjasd;flk... View all property information
Make Enquiry
From
$276
Per Night
1 / 11
The Loop
2 Bedrooms, 1 Bathroom, Sleeps 6
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Chicago Vacation Rental License # 2083779 Beautiful Victorian four-flat in the heart of Old Town, at Eugenie and Sedgwick Streets. This 700 square foot, 2-bedroom, 1-bathroom unit includes one queen size bed, one double bed, a lovely living room with a sleeper sofa and a newly renovated kitchen.... View all property information
Make Enquiry
From
$172
Per Night
1 / 12
The Loop
1 Bedroom, 1 Bathroom, Sleeps 2
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
30 Day Minimum Rental This charming one bedroom apartment is found on a quiet tree lined street tucked away in Old Town, close to the intersection of North Ave. and Wells. It's ideally located just two blocks from the train, close to wonderful restaurants, interesting shops and the lakefront.... View all property information
Make Enquiry
From
$368
Per Night
1 / 35
Payment Protection
The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 5
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Stay in luxury at this awesome penthouse unit in the South Loop of Chicago. Beautiful Lake views and a spacious 2 bedroom 2 bathroom apartment in the award winning Lex building. Chinatown and downtown are just a stone's throw away when you stay at this apartment. View all property information
Make Enquiry
From
$337
Per Night
1 / 12
The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Chicago Vacation Rental License # 2083784 This 1200 square foot, two bedroom, two bathroom unit is located within a Victorian four-flat in the heart of Old Town, at Eugenie and Sedgwick Streets. There are two queen size beds, a lovely living room with a sleeper sofa and a newly renovated kitchen.... View all property information
Make Enquiry
From
$2,483
Per Month
1 / 11
The Loop
1 Bedroom, 1 Bathroom, Sleeps 2
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
A charming one bedroom condo in Chicago's elite neighborhood! This affordable condo sits right on Lake Shore Drive which puts you across the street from Chicago's finest beaches, the lakefront path, and the Magnificent Mile! Enjoy a drink, or barbecue dinner from the 3-tiered rooftop deck with... View all property information
Make Enquiry
Enquire for rates
1 / 4
Payment Protection
The Loop
1 Bedroom, 1 Bathroom, Sleeps 1
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa... View all property information
Make Enquiry
From
$4,705
Per Month
1 / 3
The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
This contemporary two bedroom, two bathroom apartment is located on the 2nd floor of a new high-rise in the downtown area of Chicago, near the intersection of Fulton Market and Halsted St. There is one king and one queen size bed, two full bathrooms, a living room with a sleeper sofa and a fully... View all property information
Make Enquiry
From
$5,097
Per Month
1 / 20
The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
This 2-bedroom, 2-bath townhome in prime Lincoln Park, near the intersection of Lincoln Ave and Dickens. Great restaurants, shopping, entertainment and conveniences are all at your doorstep in this quintessential Chicago neighborhood. Newly refurnished apartment, beautiful kitchen with breakfast... View all property information
Make Enquiry
From
$337
Per Night
1 / 14
The Loop
4 Bedrooms, 2 Bathrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • Hot Tub
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
30 Day Minimum Rental Located right by one of Chicago's best breakfast joints, this 4 bedroom, 2 bathroom Lincoln Park vacation rental includes a bright, spacious kitchen and newly appointed living and sleeping quarters. Light hardwood flooring, granite countertops, flat-screen TV - perfect for a... View all property information
Make Enquiry
From
$306
Per Night
1 / 7
The Loop
4 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
30 Day Minimum Rental The tree lined streets of picturesque Orchard Street lead you the way to your stylish and spacious home away from home. Near the intersection of Deming and Orchard the location is fantastic with tons of local flavor and neighborhood charm. The park, DePaul campus, boutiques,... View all property information
Make Enquiry
From
$306
Per Night
1 / 9
The Loop
3 Bedrooms, 2 Bathrooms, Sleeps 7
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
30 Day Minimum Rental Get an authentic Chicago neighborhood experience in this beautiful three bedroom, two bathroom unit is located right in the heart of Chicago's hugely popular Bucktown neighborhood. Countless world class boutiques and restaurants are within walking distance. This rental... View all property information
Make Enquiry
From
$4,141
Per Month
1 / 15
The Loop
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
This 2-bedroom South Loop loft is perfect for extended stays for those looking to take in Chicago's cultural side. Walk to the Field Museum, Adler Planetarium, Shedd Aquarium, Soldier Field, the Lakefront Path, and Grant Park. Take in summer music festivals, the Printer's Row literature fest, or... View all property information
Make Enquiry
From
$429
Per Night
1 / 33
Payment Protection
The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 5
Booking
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Michigan Avenue at 21st street 2BR / 2Ba 1100ft2 w/d in unit attached garage (extra fees) Welcome to the LEX Chicago -- far from your typical Chicago rental. The LEX offers unparalleled amenities, upscale stylish accommodations, and floor-to-ceiling dynamic views of the Chicago skyline. This... View all property information
Make Enquiry
From
$337
Per Night
1 / 10
The Loop
4 Bedrooms, 2 Bathrooms, Sleeps 10
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
30 Day Minimum Rental Beautiful natural light pours into this spacious 4-bedroom Lincoln Park vacation rental. Host friends with a beautiful kitchen, or step out into the heart of a famous Chicago neighborhood. Out your door you'll find micro-brews at Atlas Brewing Company, deep dish pizza at... View all property information
Make Enquiry
From
$490
Per Night
1 / 32
Payment Protection
The Loop
1 Bedroom, 1 Bathroom, Sleeps 5
Booking
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Welcome to LEX CHICAGO! This is the ultimate Chicago Hot South Loop Experience. Jaw-dropping views from the moment you walk into the condo - direct views of the ENTIRE CITY from this modern sky-home. This is not to be missed! View all property information
Make Enquiry
From
$429
Per Night
1 / 17
The Loop
4 Bedrooms, 2 Bathrooms, Sleeps 10
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
The Biddle House vacation rental apartment in historic Old Town is located on a quiet tree-lined street, walking distance to many wonderful restaurants, shops and the lakefront. Public transportation is terrific from this location – you can take the train (brown line) downtown in just 10 minutes!... View all property information
Make Enquiry
From
$214
Per Night
1 / 8
The Loop
2 Bedrooms, 1 Bathroom, Sleeps 5
Details Make Enquiry
Amenities & Details
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Chicago Vacation Rental License # 2120297 The Biddle House is located in historic Old Town on a quiet tree-lined street, walking distance to wonderful restaurants, shops and the lakefront. Public transportation is a breeze from here - get downtown in 10 minutes on Chicago's famous El train (brown... View all property information
Make Enquiry
From
$366
Per Night
1 / 23
Payment Protection
The Loop
1 Bedroom, 1 Bathroom, Sleeps 4
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Check out the brand new sleek skyscraper at One Eleven West Wacker. This building directly borders River North and the Chicago Loop...close to all nightlife, dining, entertainment, and the Chicago River. Location IS everything here. This condo sleeps four comfortably and is brand new. Quartz... View all property information
Make Enquiry
From
$366
Per Night
1 / 44
Payment Protection
The Loop
1 Bedroom, 1 Bathroom, Sleeps 4
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Experience high rise living in a state of the art building that has just opened up this summer of 2014. This building has everything you could ever want from a brand new high rise off Wacker Drive in Chicago. Location is ideal for anything that you are looking to experience in the city. View all property information
Make Enquiry
From
$306
Per Night
1 / 10
The Loop
3 Bedrooms, 2 Bathrooms, Sleeps 7
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Chicago Vacation Rental License # 2246788 This gorgeous 3 bedroom 2 bathroom unit is located on Damen Avenue, just steps away from the city's most trendy boutique shops and restaurants. The apartment will sleep 7 comfortably in beds, with one queen, two twins, one day-bed with a trundle, and a very... View all property information
Make Enquiry
From
$214
Per Night
1 / 12
The Loop
2 Bedrooms, 1 Bathroom, Sleeps 5
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Chicago Vacation Rental License # 2093472 Bucktown House is a fully renovated 1890s coach house with two two-bedroom apartments available for rent by the day, week or month. Loaded with all of the amenities any visitor would need for a comfortable stay, this property is situated on a quiet,... View all property information
Make Enquiry
From
$337
Per Night
1 / 12
The Loop
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
30 Day Minimum Rental If you’re looking for a taste of historic Chicago, this apartment is a perfect fit for you! Located in the heart of Old Town, these great units (we have four!) are surrounded by some of the best restaurants, bars, and shopping Chicago has to offer. You will not go hungry with... View all property information
Make Enquiry
From
$306
Per Night
1 / 31
Payment Protection
The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
About this property
GRAND OPENING JULY 1ST!! 60-story Ultra-Modern Luxury Condo on the Chicago River. This unit is fully-furnished with modern decor and is the ultimate Chicago luxury condo. Lake and city views on this massive 2br corner unit are expansive and breathtaking. Sent from my iPhone View all property information
Make Enquiry
From
$276
Per Night
1 / 12
The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Chicago Vacation Rental License # 2348501 You'll love your Chicago vacation in this newly renovated, spacious, two-bedroom, two-bathroom oasis in the heart of Lincoln Park. Each unit has dark, hardwood floors, updated kitchen, and an open concept living space. Located at 2835 N. Clark Street, the... View all property information
Make Enquiry
From
$331
Per Night
1 / 4
The Loop
1 Bedroom, 1 Bathroom, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Experience the vibrancy of down town Chicago and delight in the modern, sleek comfort of wyndham grand Chicago river front — an intimate haven on the magnificent mile — offering chic accommodations in an exceptional setting. Just outside your door is Chicago's premier shopping avenue with over 450... View all property information
Make Enquiry
From
$490
Per Night
1 / 7
The Loop
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Beautifully done high-end furnished 3 bedroom | 2 bath | located downtown Chicago Beds: 1 King Bed, 2 Queen Beds View all property information
Make Enquiry
From
$276
Per Night
1 / 12
The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Chicago Vacation Rental License # 2348504 You will be sure to enjoy your stay in Chicago in this newly renovated, spacious, two bedroom and two bathroom oasis in the heart of Lincoln Park. Each unit is complete with dark, hardwood floors, updated kitchen, and an open concept living space. Located... View all property information
Make Enquiry
From
$613
Per Night
1 / 10
Payment Protection
The Loop
2 Bedrooms, 1 Bathroom, Sleeps 6
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
About this property
Modern luxury One bedroom with queen size bed Location, Location, Location Hotel type amenities. Queen size bed in your private room 900 square feet space Sleeps 4 Flatscreen TV in the livingroom Wireless Internet is not available Clean freshly-washed white sheets and white Towels waiting for... View all property information
Make Enquiry
From
$214
Per Night
1 / 12
The Loop
2 Bedrooms, 1 Bathroom, Sleeps 5
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Chicago Vacation Rental License # 2093472 Bucktown House is a fully renovated 1890s coach house with two two-bedroom apartments available for rent by the day, week or month. Loaded with all of the amenities any visitor would need for a comfortable stay, this property is situated on a quiet,... View all property information
Make Enquiry
From
$121
Per Night
1 / 4
The Loop
1 Bedroom, 1 Bathroom, Sleeps 2
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Chicago Vacation Rental License # 2233295 Located in the Heart of Chicago’s prestigious Gold Coast these 5 studio apartments offer an exclusive location, comfortable living and unbeatable value. You are within a few moments walk of some of Chicago’s most prestigious landmarks and attractions... View all property information
Make Enquiry
From
$306
Per Night
1 / 9
The Loop
3 Bedrooms, 2 Bathrooms, Sleeps 7
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
30 Day Minimum Rental Get an authentic Chicago neighborhood experience in this beautiful three bedroom, two bathroom unit is located right in the heart of Chicago's hugely popular Bucktown neighborhood. Countless world class boutiques and restaurants are within walking distance. This rental... View all property information
Make Enquiry
Go to map view
Book Online(22)
Use filters to find the best results!

Neighbourhood

  • All (276)
  • DePaul (10)
  • East Side (0)
  • Gold Coast (11)
  • Hyde Park (0)
  • Lakeview (23)
  • Lincoln Park (3)
  • Lincoln Square (3)
  • Near North Side (65)
  • Near South Side (0)
  • Northwest Side (25)
  • O'Hare (0)
  • Pilsen (1)
  • Rogers Park (7)
  • Roscoe Village (7)
  • Southwest Side (2)
  • The Loop (90)
  • University Village / Little Italy (0)
  • West Town (2)
  • Wicker Park / Bucktown (5)
Learn about Chicago neighbourhoods

Suitability

  • Wheelchair access (18)
  • Elder access (19)
  • Suitable for children (11)
  • Pet friendly (13)
  • Smoking allowed (0)

Amenities

  • Internet (19)
  • Air Conditioning (17)
  • Other outdoor space (14)
  • Parking (11)
  • Washer/Dryer (11)
  • View all amenities