How to Spend a 24-Hour Staycation in Downtown Chicago

Tourists rarely make it out of Downtown Chicago to explore what the city’s neighborhoods have to offer, and locals looking to play tourist can gain a new perspective by spending the weekend there. For all the big chains and kitschy tours, there are world-class attractions, bars, and restaurants you can enjoy by just hopping on the El. For some inspiration, check out Eater Chicago’s ideal itinerary for a staycation weekend in Downtown Chicago.

Where to Stay

There is no shortage of great hotels downtown, which means you have plenty of options based on your budget and priorities. If you want to break up the day with a bit of lounging, the Viceroy Chicago on the Gold Coast features a rooftop pool with a view of a sliver of Lake Michigan through the skyscrapers. The InterContinental Chicago Magnificent Mile puts you in the heart of the action, while Virgin Hotels Chicago has quirky charms and a free happy hour if you sign up for their loyalty program. If you’re looking to splurge, the St. Regis Chicago Hotel has amazing waterfront views, two excellent restaurants, nightly champagne sabering, and the city’s only Forbes 5-star spa.

Other reservations

Many restaurants on this list can book up well in advance for peak weekend times, so be sure to plan ahead to avoid having to wait for a walk-in spot. Some museums and other experiences can also sell out, so keep that in mind if there’s anything you definitely don’t want to miss.

Friday Evening

Happy Hour and Dinner

Barry Brecheisen/Eater Chicago

Check into your hotel and start relaxing with a drink and a snack without walking back out the door. That can mean rooftop drinks at Cerise or Pandan, ceviches and sake cocktails at Richard Sandoval’s new Nikkei spot Casa Chi, or a negroni and some fluffy focaccia brushed with rosemary and sea salt at Bar Tre Dita. After that, venture out for some dinner at one of celebrity chef Carlos Gaytán’s two downtown restaurants. Tzuco on the Gold Coast features a gorgeous covered patio and an open kitchen cooking up Mexican fare with French techniques, including whole red snapper and cochinita pibil. Ummo in River North offers fluffy housemade ricotta tortellini in lamb ragu, perfectly cooked New York strip, and creative desserts. Both serve excellent cocktails with or without spirits, so you can decide to keep the buzz going or slow down to make it easier to wake up early the next morning. Another option is Kyuramen, a Japanese chain that specializes in ramen and omurice — fluffy omelets beneath a bed for fried rice.

Saturday

Coffee and Pastries

Start the day with a snack and a bit of caffeine to get you going. If you’re at the Viceroy, head downstairs to Somerset for La Colombe nitro coffee and fresh-baked kouign-amann or a croissant filled with gooey, warm chocolate and do some people-watching from the sidewalk. Otherwise head to one of several downtown locations of Paris Baguette, which offers traditional French pastries as well as Asian-inspired snacks like choux cream bread and mochi doughnuts. A new contender is Tary Bakery a coffee shop serving Kazakh cuisine and pastries.

A Stroll Through the Park

Once you’ve gotten a bit of energy, it’s time to visit Chicago’s backyard: Millennium Park. Go early to avoid the rush to take a picture of your many reflections in Cloud Gate aka The Bean and stop to smell the flowers in Lurie Garden. The park hosts free workout classes on the Great Lawn most Saturdays during the summer, so bring a mat and workout clothes for Pilates, yoga, or cardio kickboxing. You’ll be rewarded with loose muscles and a coupon for a free mimosa with an entree if you stop for brunch at Double Clutch Brewery. If you’re not up for that, take the extra time to stroll around Maggie Daley Park and then head to The Berghoff. A true Chicago institution, the Loop restaurant has been serving bratwurst, schnitzel, and Bavarian pretzels for more than 125 years, though they recently added a craft brewery where you can try beers inspired by the Art Institute of Chicago to prepare you for your next stop.

Museum Visit

Located right next to Millennium Park, the Art Institute of Chicago offers free guided tours of the galleries (with your discounted Chicago resident admission ticket) or you can wander on your own browsing masterpieces from Vincent van Gogh, Diego Rivera, Edward Hopper and Georgia O’Keeffe and sculptures from ancient Egypt and Mesopotamia. If art’s not your favorite subject, walk down to the Museum Campus to visit the Field Museum. It’s home to a massive collection of fossils, including the largest dinosaur ever discovered, plus regularly changing scientific exhibits. Both museums can take you all day to explore, so if you’re looking for a shorter outing, swing by the Shedd Aquarium to see sea life from the Great Lakes and around the world including sharks, sea horses, and otters.

Take a Break Before Dinner

Chris Peters/Eater Chicago

Give your feet a rest by heading back to your hotel for a nap or a soak - the St. Regis and InterContinental both have indoor pools. If the weather’s nice and you want to stay out, head to The Northman Beer & Cider Garden on the Chicago Riverwalk and order something refreshing to sip while watching the boats pass by and maybe petting some of the pups that frequent the spot.

Do an early dinner to make time for some entertainment. Avec, which had a cameo in The Bear, serves Mediterranean-inspired small plates like chorizo-stuffed bacon-wrapped dates and hummus with a hearth-baked pita. Kindling within the Willis Tower offers live-fire dishes from James Beard Award-winning chef Jonathon Sawyer — you can come early for happy hour at the bar to snack on oysters and Nashville hot chicken tenders.

See a Show or Make Your Own

Browse Broadway in Chicago to see what’s playing in the Chicago Theatre District and catch a musical like Six or The Book of Mormon. The Goodman Theatre hosts a mix of big productions and more eclectic entertainment including long-form improv, spoken word, and magic shows. You can also watch movies from around the world at the Gene Siskel Film Center. If you’re looking for something more active (or to keep the fun going after the show) head to Brando’s Speakeasy for some raucous karaoke.

Grab a Nightcap

Have a drink back at your hotel or one of downtown’s many excellent cocktail bars. The Berkshire Room has an extensive menu organized by flavor, spirit, and glassware and you can just give your preference for all three to the bartender and have them whip up something special. Escape to the tropics at Three Dots and a Dash, a speakeasy hidden in an alley serving strong sippers in funky glassware. Arbella boasts Saturday DJ sets, an extensive old fashioned selection, and a drink menu packed with unusual ingredients including peanut butter and jalapeno-poblano pesto.

Sunday

Boozy or booze-free brunch

Barry Brecheisen/Eater Chicago

Check out and stow your bags to spend the day doing some more eating and exploring. Start with a leisurely meal at Planta Queen, which offers bottomless brunch cocktails plus Asian-inspired vegan fare like scallion pancakes, bang bang broccoli, and sesame peanut noodles. Opt for a Vietnamese iced coffee or oat milk matcha if you had enough to drink the night before. Those who want to start the day with some real meat and eggs can head to Alpana for bottomless mimosas, crab cake benedict, and steak & eggs.

Hit the water

A Chicago River cruise is one of the city’s top tourist attractions for a reason — it’s a laidback way to enjoy the views and learn a little about Chicago and its dramatic skyline. The Chicago Architecture Foundation’s 90-minute cruise is packed with information, though the 45-minute cruise from Wendella is far from remedial. No matter how long you’ve lived here, chances are you’ll pick up something new. If you’ve already taken the tour with visiting friends and family, opt for a more active outing with Urban Kayaks. Depending on your skill level and how long you want to paddle you can take an intro lesson along the Chicago Riverwalk, get a two-hour history tour, or spend up to four hours exploring.

Play with Your Food

Chicago has plenty of interactive museums and exhibits, but the best of these is the Museum of Ice Cream because it offers as many frozen treats as you want. Board the bright pink version of the El, play mini golf, and try an ice cream version of a Chicago hot dog that’s not as gross as it sounds. You can also just head for the equally Instagram-famous BomboBar for gelato and Italian doughnuts.

One Last Big Dinner

Ashok Selvam/Eater Chicago

The West Loop is jam-packed with top-tier restaurants for you to finish out your weekend even if you didn’t plan ahead far enough to book one of its acclaimed tasting menus. Chef Paul Virant’s Gaijin specializes in okonomiyaki, savory Japanese pancakes served sizzling on tabletop griddles, as well as kakigori cocktails. Tamu, the new spot from chef BK Park (Mako), offers reasonably priced omakase and walk-in seating for hand rolls and kaisendon. Stephanie Izard’s Girl & The Goat helped establish the neighborhood’s Restaurant Row, while Proxi offers a la carte dishes or a four-course menu spotlighting global street food from tamales to kabobs to Thai curry. Toast to a great trip with a drink at CH Distillery (makers of Jeppson’s Malört) and then head back to your hotel to pick up your bags and go home. You can always come back downtown for more.