Chicago travel tips for first-time visitors
Our mayor is very keen on the idea of building a new express train from O’Hare International Airport to downtown—which would be great for business travelers and no one else, really. Most of the actual Chicagoans we know are just happy that our regular Chicago Transit Authority El trains offer direct service to both of our 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.
It’s not advisable to rent a car if you’re planning to spend all of your visit in 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: $20 for unlimited rides for 72 hours will get you everywhere you want to go. If you’re staying longer, a seven-day pass on a new Ventra card will run you $33—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 El station.
If you’re driving into the city and you want to use your car while you’re here, download ParkChicago (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 like this one 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 or Apple Maps 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 App is our favorite for real-time arrival projections for El 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. Check out more transportation apps we love here.
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.
In a city of almost 3 million people, delays are almost bound to happen whether you’re on the El 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 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—maybe 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.
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 some 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 you shouldn’t count on it.
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.
The Chicago Architecture Foundation’s boat tours along the Chicago River are, frankly, one of our favorite reasons to have out-of-town guests; we’ve been known to take them for a sunny afternoon of getting acquainted with our favorite skyscrapers even when we don’t have visitors. It’s just one of dozens of the best tours of Chicago, including walking tours, bike tours and even the highly conspicuous Segway tours. You can also find food tours or brewery tours to maximize your use of time.
Chicago’s terrain is relatively flat—not 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—and we have—but it’s hard to deny that summer is when visitors and residents alike can really take the best advantage of what the city has to offer. With another long winter under our belts, Chicagoans scramble to get outside: to outdoor dining and rooftop bars, to 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.
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 here with our neighborhood guides.
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, 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. 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 Lagunitas 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.
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 or Kerry James Marshall to mosaics by Marc Chagall to sculptures like Lorado Taft’s Fountain of Time. Soon, even the enormous facade of the Merchandise Mart will become a canvas for video art.
We’ve heard scary stories about those towns where the sidewalks are rolled up at 9pm. Chicago’s not like that. True, it’s not always easy to find a late-night meal or drinks in the Loop—though that’s changing as downtown is becoming more residential. But most bars and clubs in the city, from neighborhood corner taverns to bumpin’ dance clubs, are open until 2am every night (3am on Saturdays). And when they close, the most dedicated partiers among us head to one of the more than 100 bars that are licensed to pour drinks until 4am (you guessed it, 5am on Saturdays). These are our favorite 4am bars. When they kick you out, soak up the booze with a meal at a 24-hour restaurant; soon enough, our favorite coffee shops will be open for the morning crowd.
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 or Andersonville.
The big musicals that visit 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 if that’s what brings you here. But Chicago’s homegrown theater isn’t centralized around a theater 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 game 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 iO or the Annoyance, and many more of the city’s best comedy nights take place in bars, bookstores and other non-theater venues.
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 on Argyle Street, killer old-school steakhouses. 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.