Chicago, Illinois, is the third-biggest city in the country but somehow manages to maintain the “Midwest Nice” reputation the region is known for. Our itinerary will introduce you to a mix of Chicago’s most-loved neighborhoods, sights, restaurants, parks and shops.
Visit the Windy City’s iconic spots — the Bean, Wrigley Field — but also venues for vintage vinyl, artisanal cocktails and, you knew this was coming, Chicago-style pizza (while it’s not actually illegal to skip this deep-dish delicacy, we wouldn’t recommend it).
As always, check for travel restrictions and closures before planning your trip.
Friday: Take in the Iconic Sites of Millennium Park
After grabbing a classic Midwest diner breakfast — we suggest Eggy’s Diner or Wildberry Pancakes — head toward Millennium Park. This area is filled with public art installations, including “the Bean,” a giant reflective bean-shaped sculpture designed by artist Anish Kapoor.
After negotiating its selfie-taking throngs, take a few meditative minutes to walk through the nearby Lurie Garden. If you’re lucky, you’ll catch the sounds from a performance at the adjacent Jay Pritzker Pavilion.
Other sites to add to your Millennium Park itinerary: Boeing Galleries, the free Chicago Cultural Center, Crown Fountain and Maggie Daley Park (home of a rock-climbing wall designed by architect Michael Van Valkenburgh).
Once you’ve had your fill of Millennium Park, book a ticket for a Chicago River Boat Architecture Tour. After stepping aboard, the guide will talk you through the history of Chicago’s skyline and stories behind some of the city’s most iconic Art Deco buildings. All in all, leave with new knowledge of 50 skyscrapers, bridges and other historic sites seen from the water.
Once hunger hits, head to the nearby River North neighborhood, known for its top-notch dining. Try Bavette’s Bar & Boeuf for steak, Tzuco for Mexican fare, or the beloved Portillo’s for a classic Chicago dog.
Saturday: Sip and Shop in Wicker Park
Follow up a day in the heavily-trafficked destination of Millennium Park with a more leisurely exploration of Chicago’s hippest neighborhood. Wicker Park is located northwest of the downtown area and is full of small businesses, bars, vintage stores, record shops and really good coffee. Kick off the morning with a pancake you’ll dream about from Dove’s Luncheonette.
After filling up, plan a slow stroll down Milwaukee Avenue — this is where you can find most of the eclectic shops the neighborhood is known for. Don’t miss Reckless Records, Saint Alfred, Myopic Bookstore, Penelope’s, and Pistil & Vine.
Make sure to take a break for a drink or two. The neighborhood is full of great options, but cocktail aficionados will especially appreciate the Violet Hour or the Revel Room.
The lunch and dinner choices are plentiful in Wicker Park, but make a reservation if you’re hoping to visit one of the area favorites. Our tip: Call beforehand to get into Schwa, where cell phones aren’t allowed and a minimal corkage fee means you can bring your own bottle of wine.
Round out the day with a show. Plan ahead and look into the lineup at Subterranean, a live music venue built on top of secret Prohibition-era tunnels. For theater, check out the Broken Nose Theatre, a pay-what-you-can venue with a massive variety of performances.
Sunday: Check Out Magnificent Mile and Navy Pier
Get yourself in breakfast mode and head to Kanela Breakfast Club, which plates up Greek-accented egg and pancake dishes, plus cinnamon-flavored rolls and monkey bread (kanela translates to “cinnamon” in Greek).
From there, walk over to the Magnificent Mile, which is the heart of the downtown shopping district. There are 460 stores and three shopping centers, ranging from major retailers to luxury designers and everything in between. This is the place to go if you’re looking to bask in the energy of a lively crowd.
A few highlights for shoppers: Mary Mary Gifts, Tory Burch, Max Mara, OSKA, and Patagonia.
Once you’re loaded with shopping bags, take a break for lunch. A trip to Chicago is not complete without sampling the city’s take on pizza: a cheesy treat that’s structured more like savory cake than your traditional pie. It’s a mess to eat and completely worth the effort.
Giordano’s is a name known around the world for its deep-dish pizza, and there’s a location right on Navy Pier. Spend some time with this pie — it’s meant to be savored.
Follow up a heavy (and satisfying) lunch with a walk down Navy Pier. The expansive views of Chicago’s skyscraper-dotted skyline are worth the trip — you’ll find it hard to believe you were in the center of a shopper’s crowd and surrounded by soaring buildings hours earlier.
There are plenty of rides and games for the kids, not to mention the Chicago Children’s Museum. Adults will enjoy the Navy Pier Beer Garden and the Polk Bros Park, which often hosts free events. Finally, head to East End Plaza for the best views of the city.
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