Chicago travel guide: 27 tips every first-time visitor needs to know

Beat the traffic and surcharges by skipping the taxi or rideshare when you arrive. Our regular Chicago Transit Authority "L" (short for "elevated") trains offer direct service to both Chicago airports: The Blue Line serving O’Hare and Orange Line for Midway International Airport. A $2.50 fare from Midway or $5 from O’Hare for regular service downtown in under an hour feels like a steal to us when we travel to other cities without such easy airport access.

No need to rent a car if you're sticking close to the city. In the smartphone age, the CTA is easy enough to navigate even for newbies. Fares, though, can be a little harder to keep track of: You could load a dollar amount onto a Ventra card and then try to do the math every time you spend $2.50 on a train ride and $2.25 on a bus—or maybe that counted as a $0.25 transfer if it was within two hours of your last ride? Much easier to buy a three-day pass, which is $15 for 72 hours of unlimited rides. If you’re staying longer, a seven-day pass on a new Ventra card will run you just $20—totally worth it if you’re spending that much time here. All can be purchased from the Ventra vending kiosks at either airport and any CTA station, as well as many supermarkets and pharmacies.

If you’re driving into the city and want to use your car while you’re here, download the ParkChicago app (parkchicago.com) to your phone for all your street parking needs. Create an account with your license plate number and link a credit card, and you’ll pay in the app using the zone number printed on signs where paid street parking is available. Rates vary by neighborhood (many residential streets will be marked permit-only, while a blessed few unmarked streets are actually free to park on—check carefully for signage before you assume).

Google Maps, Apple Maps or Waze will give you solid directions, and the Uber and Lyft apps can find you a ride at just about any address and any time of the day or night (most rideshare drivers work for both services, in our experience). Transit is our favorite for real-time arrival projections for "L" trains and bus routes, and if you’re a nervous navigator, you can tell the app exactly where you’re going and it will give you a heads up when your stop is approaching.

Unlike a lot of cities, Chicago’s streets are laid out on a generally reliable grid system. Here’s the quick-and-dirty version: The intersection of State and Madison Streets, smack in the middle of the Loop, is the zero point of the grid. Street numbers fan out from there on north-south and east-west axes, and every eight blocks (outside of the Loop, at least) equals a mile. There are angle streets and river branches and historical quirks here and there to create confusion and six-corner intersections, but the grid is a solid foundation for getting around. Also, if you remember nothing else, east is always towards the Lake. 

In a city of almost 3 million people, delays are almost bound to happen whether you’re on the "L" or on the expressway (which, by the way, is what we call our controlled-access highways, a.k.a. freeways, interstates or motorways). If you’re trying to make an appointment with a rigid start time—whether it’s a meeting, a dinner reservation or a theater curtain—allow more time than you think you need, just to be safe.

In the United States, tipping is customary for service in several situations, and the standard rates in Chicago may be higher than you’re used to elsewhere in the country. At sit-down restaurants, where you have a server taking your order at your table and seeing to your needs through your meal, you should tip at least 20 percent of your total bill for good service. If you’re out for drinks, a dollar per drink is usually fine if you’re ordering from the bar—more if they’re complicated cocktails.

If the establishment accepts credit cards, you can add the tip onto your total when you sign the bill. Many restaurants and coffee shops also now have a payment system that allows you to add a tip automatically to your bill via credit or debit card, and calculates the percentage for you.

Other situations will call for cash tips: Give a valet parking attendant a couple of dollars when they retrieve your car, and tip a bellhop or skycap a buck or two for each of your bags they handle. Hotel housekeeping staff should be tipped about $5 per day of your stay, which you can leave out in the room when you check out.

While it’s increasingly uncommon, there are a remaining few cash-only venues around the city that don’t accept credit cards—among them, some of our favorite dive bars and cheap eats establishments. It’s also good to have cash on hand if you’re planning on visiting any summer street festivals or looking to make a purchase at art or craft fairs; many small vendors can now accept credit cards via services like Square, but it's a good idea to bring cash just in case (and to avoid the high fees that are often found at on-site event ATMs). 

Whether you’re a business commuter or a tourist, unless you’re driving your own car everywhere you go you’ll probably be carrying a purse, tote, briefcase or bag of some kind to lug your stuff around. Security precautions at certain large venues—stadiums and ballparks, theaters, concert venues and music festivals—will mean an agent asking to take a cursory peek inside your bag before you go in; it’s standard practice. Certain venues, though, won’t allow very large bags or specific items inside at all, and they won’t be able to hold anything for you at the gate or the cloakroom. If you don’t want to find yourself making a trip back to your car or hotel and missing part of your event, it’s best to check the rules ahead of time.

You can stay in a Hyatt or a Hilton anywhere you go. When you’re here, splurge instead on one of the best hotels in Chicago—unique digs like the Chicago Athletic Association or the Emily Hotel. Or look at the city’s best boutique hotels, gems like the Freehand, Hotel Lincoln or the Robey.

Rent out an extravagant apartment or a homey condo for the duration of your stay—we’ve chosen some of the city’s most attractive options here.

The Chicago Architecture Foundation’s boat tours along the Chicago River are, frankly, one of our favorite reasons to have out-of-town guests (and they're fun to check out even when we don't have out-of-town guests). It’s just one of dozens of the best tours of Chicago, including walking tours and bike tours. You can also find food tours or brewery tours of some of the city's best spots.

The unnamed Picasso sculpture in Daley Plaza and, more recently, Millennium Park’s Cloud Gate (a.k.a. “The Bean”) have become symbols of the city. But there’s great public art to be found all over the place in Chicago, from murals by Hebru Brantley to mosaics by Marc Chagall to sculptures like Lorado Taft’s Fountain of Time. Even the enormous facade of the Merchandise Mart has become a canvas for video art with the ART on THE MART program.

Chicago’s terrain is relatively flat and you won't find many hills to climb, unless you’ve built a side trip to one of our nearby hiking trails into your visit. But you’ll probably wind up doing more walking than you might think. Our city blocks are long, and both CTA stations and parking spots can be a good distance from your destinations.

The weather in Chicago can fluctuate wildly in a matter of hours: Summer storms roll in out of nowhere, or the temperature rises 30 degrees Fahrenheit from morning to midday. If you’re going to be out on the town all day, it’s best to dress with options to shed or layer on as the day progresses. Even at the height of summer or winter this is true: Pitchfork or Lollapalooza summer festival attendees in tank tops and short-shorts often find themselves wishing for a hoodie when the evening chill sets in, and there’s nothing worse than the overheated feel of being too bundled up on a packed CTA car in January.

We can make a great case for every season in Chicago, but it’s hard to deny that summer is when visitors and residents alike can take the best advantage of what the city has to offer. After a long winter, Chicagoans scramble outside to outdoor dining and rooftop bars, our great public parks, Cubs and White Sox games, and of course to one of Chicago’s finest features—the 26 miles of beaches and open lakefront that make up the city’s eastern edge. We take our summers seriously.

We’ve already breathlessly sung the praises of summer in Chicago, but summer festival season deserves a shoutout all its own. Every weekend from spring well into autumn, there are multiple lively festivals to choose from, each with delicious food, live music and other fun activities to explore. From art fairs and cultural and LGBTQ+ festivals to exuberant, jam-packed concerts and celebrations of a specific food or drink item (e.g. Ribfest, Apple Fest and Burger Fest), there’s truly something for every taste.

A lot of the city’s hotels are clustered in River North, on the Mag Mile and in the Loop. Not coincidentally, so are a lot of chain restaurants and tourist traps. (It’s no surprise the only TGI Friday’s in the city is just off Michigan Avenue). Just like visiting Times Square doesn’t mean you’ve seen New York City, if you want to see how Chicago really lives, you’ll need to venture out into the neighborhoods. We like to call this a city of neighborhoods, and each area of the city has its own identity and attractions. Start with our guide on where to stay in Chicago.

Remember we said you’d be doing a lot of walking? A good chunk of that could take place inside Chicago’s must-see museums. The Art Institute alone is the second-largest museum in the United States by size—at over a million square feet and with 300,000 pieces in its collection, don’t expect to knock it off your list in an afternoon. You’ll have to pay admission to most of the big institutions; free days are generally offered only to Illinois residents, but a Chicago CityPASS is a good way to get discounted admission to several attractions. And plenty of smaller free museums and galleries never charge admission and are definitely worth your while.

While Chicago has always been a beer-loving city, there was a dark period of a decade or so after Peter Hand Brewing closed in 1978 when no beer was actually being made here. The closest you could get to a “local brew” was stuff from Milwaukee. But in the late ’80s and early ’90s, a few hops-headed entrepreneurs launched Chicago’s first brewpubs, where beer was made and drank on the same premises. One of these, Goose Island, made its first foray into bottling and distribution in 1995; within another decade, the craft beer boom had begun. Now, Goose sits alongside names like Half Acre, Revolution and Marz on any list of Chicago’s best breweries, but there are well over 100 breweries operating in the city and suburbs, many of which have attached taprooms and offer brewery tours, and events like FOBAB (Festival of Barrel-Aged Beers) and Illinois Craft Beer Week have become tourist draws all their own.

We like Chicago-style deep dish pizza, trust us. But it’s not exactly a staple of our diets—in fact, we know a lot of Chicagoans who only eat deep dish when we have friends in town. There’s so much more to food in Chicago—heck, there’s so much more to pizza in Chicago. But let’s not forget we also have Michelin-starred fine-dining restaurants, great taquerias in Pilsen, Indian fare on Devon Avenue, Vietnamese food on Argyle Street, killer old-school steakhouses and much more. When it comes to the best restaurants in Chicago, there are almost no limits. Oh, but the thing about no ketchup on Chicago hot dogs? That’s real.

We mentioned the chain restaurants around Michigan Avenue. Well, these days most of the shops lining the pedestrian-packed sidewalks of the Mag Mile are also outposts of department stores and brands you can find elsewhere in the country (or even elsewhere in the city). For more unique retail, look where the locals do: great shopping neighborhoods like Wicker Park and Bucktown, Lincoln Park, Lakeview, Logan Square or Andersonville.

With more than 600 parks in the city limits, there's plenty of green space to take in. Plan the perfect morning by grabbing a pastry and coffee at one of the best bakeries in the city and taking a walk through the public parks. Millenium Park is a great first stop to see iconic landmarks like the Crown Fountain, "The Bean" and the Art Institute. But if you're looking for a more authentic and low-key saunter, we recommend venturing out toward other giant parks around the city. Try Humboldt Park to take a dip in the only inland beach in Chicago or head over to Jackson Park to admire the beautiful Osaka Garden with picturesque views of the Museum of Science and Industry. We recommend marveling at the orate gold dome fieldhouse at Garfield Park to brag to friends back home about the "hidden architectural wonders" of Chicago.

From the Michael Jordan-led Bulls dynasty in the ‘90s to recent championship titles by the Blackhawks, Cubs and Sky, Chicago prides itself on heavy-hitting sports teams and wildly passionate fans. With most stadiums easily accessible by train or bus and single-game tickets relatively affordable if you book in advance (it’s possible to get White Sox tickets for as little as $7, for example), cheering on one of the many local teams with a hot dog and an Old Style in hand is a great way to spend an afternoon or evening in Chicago. 

If you’re not much of a sports person, it still helps to know when the local teams are playing for getting-around purposes. If you’re heading north on the Red Line and the Cubs are in town, be prepared for a packed-to-the-gills train or bus and possible delays. There’s even a handy website for quick references.

Throwing back a shot of Chicago's most controversial spirit will undoubtedly get you some street credit from Chicagoans. You be the judge: Is it really as bad as they say or can you endure what some call "the worst booze ever?" Don't be too worried about how to source it—pull up to any dive bar in the city and there will definitely be a bottle.

The big musicals that do a run in the Loop under the banner of Broadway in Chicago are a major tourist draw; some visitors build their trips to Chicago around getting to see Broadway-style shows without having to go to New York. And hey, we’re not going to tell you not to see Hamilton (or whatever other marquee show is playing) if that’s what brings you here. But Chicago’s homegrown theater isn’t centralized around one district. Instead, theaters large and small have cropped up across the city and suburbs; you can catch a show in neighborhoods from Lincoln Park to Jefferson Park, Back of the Yards to Grand Crossing, and many residents become loyal subscribers of the theaters in their own backyards. Similarly, while Second City has produced a lot of famous names, it’s not the only comedy club in town for the improv and sketch comedy Chicago’s famous for. You’ll find a greater variety of shows (and possibly more comfortable seats) at Lincoln Lodge or the Annoyance, and many more of the city’s best comedy nights take place in bars, bookstores and other non-theater venues.

Sure, it's great to fill up on deep dish pizza, a Chicago-style hot dog or an Italian beef. Once you've checked those off your bucket list, though, there's plenty of other lesser-known dishes popular in Chicago that are worth the rave, too. The jibarito, originating in Humboldt Park, will have you rethinking your sandwich standard while slow-cooked rib tips popular on the South Side reveal the deep flavors of Southern cooking that made its way up the Mississippi River. Don't forget to try mild sauce with your fried chicken—your first taste of it may entice you to bring some home by the gallon.