A bustling, beautiful cosmopolis with Midwestern humility, Chicago has too often played second fiddle to its noisier coastal peers. But a lack of ocean views hasn’t stopped the Second City from blossoming from its industrial roots into a place of top-rate cultural institutions, breathtaking buildings, and diverse cuisine. Two days here will offer plenty of sites to see and things to do. Chicago is famously a magnet for architecture nerds, as the birthplace of the skyscraper and home to some of the Franks’ (Gehry and Lloyd Wright) finest creations. The renovated Riverwalk offers some of the most stunning skyline vistas in the city. It’s also no slouch in the museum department boasting all from the renowned Art Institute of Chicago to kid-friendly Museum Park to a smattering of smaller galleries. If music is more your thing, grab your flower crown and head to the festival field to enjoy the artists—and go celeb-spotting—at Lollapalooza. Along the way, you can chow down on giardiniera hot dogs, deep-dish pizza, Michelin-starred molecular gastronomy, and top-notch ethnic eats from Mexican to Macanese. Chicago is very much a segregated city—most tourists will never venture beyond the North Side—but it’s a city of fierce resilience (see: The Great Chicago Fire) and genuine heart. If you have 48 hours to spend here, this itinerary can help you get the most out of your stay.
Day one
Take in some gorgeous scenery and indulge your artistic side.
Morning: Stroll down Magnificent Mile
If you were the king of Chicago trying to impress your foreign rivals, the Magnificent Mile is where you’d want to have the welcoming parade. The River North stretch of Michigan Avenue is lined with some of the city’s finest architecture (the Tribune Tower, the Wrigley Building), most luxurious stores (Bloomingdale’s, Louis Vuitton), and slowest-walking tourists (Karen, Jim). While there are some backpacker-friendly options like H&M scattered throughout the street, it’s more fun to go into Gucci and see how much stuff you can touch before the security guy starts watching you. Or, consider a walking tour and have a local guide show you all the best sites.
If window shopping isn’t your thing, another great option is the Lincoln Park Zoo. The main selling point of the Lincoln Park Zoo—located about three miles north of the Loop, and accessible most directly via the 151 bus—is that it’s completely free. That’s not a small deal in a city of $40 museums (@Shedd Aquarium). At that price, we would’ve been satisfied with a few meerkats in a cage, but this 35-acre, 150-year-old park seriously exceeded our expectations. You’ll find creatures big (lions, gorillas, polar bears) and small (kookaburras, otters, mongooses), plus a pair of unbelievably cute red pandas named Waveland and Sheffield. Sure, you’ll have to contend with every YMCA summer camp in the great Chicago area, but there’s more than enough penguins to go around.
Lunchtime: Load up on some deep dish
When in Chicago, right? Deep dish is a must—whether or not it’s delicious or meh is up for debate, but we think you should make that decision for yourself. If you really want to get crazy, take a pizza tour. You’ll sample some of the city’s famous pie while taking in the sites.
Afternoon: Head to the top of the Skydeck
No other views in Chicago compare to the stunning scenery you’ll see from the Willis Tower. Buy a ticket and head to the 103rd floor—and be sure to have your camera ready to snap some pics.
Listen, we understand staggering heights aren’t for everyone. If the thought of being hundreds of feet in the air makes you queasy, take in the art at Chicago Cultural Center, instead. Don’t be fooled by the “Chicago Public Library” engraving on this very library-looking Loop venue—we looked hard and long for a book in the Cultural Center, and couldn’t find a single one. We did find, however, one of the city’s 100% free art galleries, showing a small but well-curated group of exhibitions with Chicago roots. Make sure to check the website and see what is on currently on display as it is continuously changing. While a lot of the building is eerily vacant—it’s mostly used as an event space—it’s architecturally interesting enough to merit a quick meander.
Evening: Grab dinner in River North
Chicago’s glam River North neighborhood attracts a sizeable after-work crowd looking for some good happy hour specials. Find a restaurant with the right ambiance that suits your mood. From pricey steakhouses to grab-and-go hot dogs to middle-of-the-road Mexican with $5 margaritas, you’ll find something for every mood in this area of the city.
Day two
Take in a museum and stretch your legs with a walk along the water.
Morning: Walk down Navy Pier to start your day
Navy Pier is having a bit of an identity crisis. Is it an old-school amusement park? A sleek foodie destination? A meeting point for every balloon artist in the Chicagoland area? Predictably, the longtime Near North Side tourist attraction tries to please everyone, and ends up missing the mark. The ferris wheel is overpriced ($18 a ride) and underwhelming, and the food court is outclassed by the enormous selection of nearby local restaurants. The 100-year-old park’s moves to modernize have stripped the once rough-around-the-edges pier of most of its character, replacing cute, kitschy shops with chain restaurants and Instagram bait. Still, the Chicago Shakespeare Theater remains a gem of the Midwest, and the simple pleasure of strolling the boardwalk at sunset — strawberry churro in hand — is undeniable.
Option two, if you’re not feeling option one, is to pop into the Field Museum of Natural History. You’ll see Máximo the Titanosaur, the largest dinosaur ever discovered. And who doesn’t love some giant dino bones? That alone is makes this museum worth a visit.
Lunchtime: Lunch at world-famous Eataly
This two-story food hall is constantly thronged with tourists, but unlike Times Square or the entire city of Las Vegas, this place actually merits the hype: the gelato is smooth, the wine fine, and the house-curdled fresh mozzarella balls perfect for shame-eating like an apple in the privacy of your room. Cheap it is not, but there are deals to be found: the summer specials (Nutella crêpes, cappuccino, and cream puff-like pastries) could legitimately be included in a budget guide, and the grab-and-go sandwiches aren’t much more than you’d pay at a corner deli. Skip the fancy upstairs restaurant and take your caprese salads and Genoa salami sandwiches to picnic by the river.
Afternoon: Walk to the Chicago Water Tower
We haven’t seen waterworks this pretty since Timothée Chalamet at the end of Call Me By Your Name. The Gothic Revival structure on an extra-bougie stretch of Michigan Avenue looks like it should be housing a small princess instead of a large water pump, its original purpose when it was built in 1869. It survived the Chicago Fire of 1871 and became a symbol of hope for people who had lost, like, their houses—Midwesterners are an optimistic bunch. Today, it’s home to a piddly art gallery, a fine photo op, and a pit stop on The Amazing Race once in a while. Stop by on your Magnificent Mile walk and marvel at the city’s super dope dedication to public infrastructure projects or take a guided segway tour for something a little different.
Not feeling the architecture? No worries. Head to Millennium Park instead. This 24.5-acre park is home to Cloud Gate (aka “The Bean”), gorgeous gardens, plenty of sculptures, and tons of places to lounge and escape the city streets. You really can’t go wrong.
Evening: Dine on Restaurant Row
Chicago’s West Loop—the area immediately west of the Loop and the Chicago River—has rightly earned this culinary nickname. Budding chefs and mixologists rule the roost here and you literally can’t go wrong no matter where you choose to eat. Pick a spot, settle in, and nosh on some of the city’s best food in one of it’s hottest neighborhoods. Stick around for a drink or two and cheers to an awesome two days in Chicago.