Tripadvisor's Destination Expert answers your top Chicago questions

Have questions about Chicago? Want to know where to eat? Where to stay? How to get to and from a Taylor Swift concert? David Rothschild, aka @dave148 to the folks on the Tripadvisor forums, has answers. As one of our designated “Destination Experts” for Chicago, Rothschild gives out traveler advice on the regular. We're talking 72,132 posts and counting. He’s a lifelong local and a self-described public transit fanatic. And while he knows the ins and outs of downtown, he’s always encouraging folks to head farther out to explore Chicago’s truly excellent neighborhoods and all the independent, long-lasting businesses that give them their character. We reached out to Rothschild to tap his wisdom and get him to answer some of your most-asked Chicago questions.

Answers have been edited for clarity and length.

Most people have heard about the Chicago Architecture River Cruise, but Rothschild has another hot tip for travelers: “Our Cultural Center downtown has what's called a Chicago Greeter, which you can reserve ahead of time,” he says. “Tell them what your interests are, so if you're interested in skyscrapers, for example, they will hook you up with a volunteer docent that will take you on a walking tour of skyscrapers.” Too late to make reservations? No worries. “They also have a thing called InstaGreeter where basically you just walk in, no reservations. And if they have somebody available, they'll just take you on a tour right there.” Rothschild notes the program is free and only open to out-of-town visitors.

“Bring a lot of money. [Wrigley Field] is real expensive,” Rothschild laughs. But deals can be had on the tickets themselves. While it’s counterintuitive, you can actually save some money by waiting until the last minute to buy them. “Buy tickets on StubHub even up to the day—you can get nice tickets at or below face value,” he suggests.

If you’re hoping for an autograph, “get there early,” he advises. “The park opens… 90 minutes before the game starts and you definitely can see batting practice. You might get lucky.” On the other hand, you can forget about getting autographs after the game, Rothschild warns.

As far as getting there, “The CTA Red Line train lets you [out] right across the street from the ballpark,” he says. “Trying to find a rideshare after or taxi after the ballgame is next to impossible. There's really no reason not to take the trains.”

For the typical traveler, Rothschild has a ready answer: “The River North or [Magnificent] Mile areas of downtown. It's more lively, there's lots of concentration of hotels, restaurants and entertainment venues.” Families with kids, on the other hand, might want to check out Chicago’s many chain hotels with indoor swimming pools, like Embassy Suites. Also keep in mind that Lake Michigan is easily accessible from the city, too, giving another opportunity for splashing around. If you’re in the mood for something luxe, there’s always The Peninsula Chicago or The Langham.

As far as scoring a deal on a hotel, Dave says it’s not just season you need to keep in mind. “Hotel rates here are cyclical because Chicago is also a convention destination,” he says. Summer prices tend to be high, too. Surprisingly, unlike many other major cities, you can score really nice hotels for good prices over the winter holidays.

“I would take the train,” Rothschild says with confidence. He ticks off the reasons to go via rail: The Blue Line takes about 45 minutes once it's moving, costs five dollars, and drops you off in the Business District. But there are some downsides. “There's not a lot of hotels within walking distance—it's not a high-traffic touristy area generally. If you're not staying in the Loop area, you'll need to take a taxi or rideshare or walk (depending on how much luggage you’ve got) to your hotel.”

Still, it’s your best option—especially for the next several years. “There's one expressway that runs between O'Hare and downtown and literally as we speak, it's getting torn up for a minimum of three years,” Rothschild says. Rideshares, taxis, and buses all use that expressway, so what used to be a 30- to 40-minute drive will now take significantly longer, not to mention cost way more. “Under normal circumstances, [the price for a taxi] is probably between 50 to 60 bucks, he says. "But since taxi rates here are metered, now the meter is clicking whether you're sitting in traffic or moving.”