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Chicago Holiday Packages

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Chicago
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Chicago Holiday Packages
Want to book a holiday to Chicago? Whether you're off for a romantic holiday, family trip, or an all-inclusive holiday, Chicago holiday packages on TripAdvisor make planning your trip simple and affordable.
Find the perfect holiday package for Chicago on TripAdvisor by comparing Chicago hotel and flight prices. Travellers like you have written 262,948 reviews and posted 51,582 candid photos for Chicago hotels. Book your Chicago holiday today!
Or build your own Chicago holiday package
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The Talbott Hotel
The Talbott Hotel
The Talbott is a lovely location in the midst of a quaint River North neighborhood. The in-house restaurant brews up some of the finest coffee in Chicago (specially roasted for...
1. Find your perfect hotel
2. Find the right flight
Build your luxury package
The Guesthouse Hotel
The Guesthouse Hotel
I stayed at this "hotel" for 4 days. It is not your usual hotel, it really is an apartment. The apartment is equipped with a full size kitchen (fridge, freezer, microwave...
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2. Find the right flight
Build your budget package
Hotel Chicago West Loop / Illinois Medical District
Hotel Chicago West Loop / Illinois Medical District
Incredible hotel! Everything is new, bathroom is spotless, full size fridge, stainless microwave, and keurig in the room!! I also happened to have a very nice view from my room...
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2. Find the right flight
Cheap Flights to Chicago
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†  Prices are based on round trip travel with returns between 1-21 days after departure. These are the best fares found by travellers who searched TripAdvisor and a select group of our fare search partners in the past 72 hours. Ticket prices and seat availability change rapidly and cannot be guaranteed.