Chicago! We love its big city vibes and Midwestern charm. Expect incredible architecture, amazing chefs, great museums and much more. Chicago is a great city to visit year round but be forewarned, the winters can be brutal! Our favorite season is early autumn as there are less crowds. Or visit in summer for the weekly festivals that take over the city’s neighborhoods.
Chicago has two major airports, Chicago O’Hare and Midway. To get into the city, from O’Hare you can take the CTA Blue line (hop on in Terminal 2) to Clark/Lake and catch an Uber or cab from there. This may help you beat the traffic if arriving during rush hour or on a game day. If coming from Midway, we recommend taking an Uber into the city.
If you are visiting the city and plan to go to several attractions, look into purchasing a CityPASS. The CityPASS bundles together the price to visit five Chicago attractions over a nine day period and saves you up to 50% on admission fees.
We’ve broken out our suggestions below by different areas of the city - Chicago Loop, North Side and Wicker Park. For the majority of our drink and dining recommendations we advise to make a reservation in advance to avoid long waits.
CHICAGO LOOP
EAT
3 Arts Club A beautiful restaurant inside the atrium of the Restoration Hardware store. This place is one of a kind and a unique spot in the city.
Au Cheval Arguably one of the best burgers, ever. No reservations are taken but it is worth the wait!
Beatrix Open for brunch, lunch and dinner, this creative restaurant puts a twist on traditional, American cuisine.
Boqueria A Spanish style tapas bar in a European bistro setting. The menu changes seasonly but the Spanish classics are menu staples.
Bub City Country western themed bar and restaurant, this spot has delicious comfort food and live country music!
Girl and the Goat Innovative, delicious small plates influenced by “nose to tail” cooking by Chicago Native Chef, Stephanie Izard.
Gibsons Bar & Steakhouse Traditional Chicago Steakhouse in the swanky, Gold Coast neighborhood.
Little Goat Diner Great brunch spot in the West Loop from Stephanie Izard. Expect fun twists on classic diner dishes.
Lou Malnati’s Chicago’s original deep-dish pizza.
Monteverde Incredibly, contemporary Italian food with great service.
Pequods Another rival Chicago-style pizza spot.
Portillo’s A city staple. This fast food spot is known for its Chicago-style hot dogs, Italian beef & sausage.
Pizzeria Portofino Outdoor dining on the Chicago Riverfront, this spot is known for its traditional hand-stretched pizzas.
Quartinos Casual Italian spot. Good for groups before a night out.
RPM Steak Trendy, upscale steak restaurant in River North. For a special occasion, start with the RPM Grand Seafood Platter, it is incredible! The beef selection is sourced globally and hand picked. One of our favorite dining experiences.
RPM Italian The sister restaurant to RPM Steak, its perfect for a special night out to enjoy well presented, delicious Italian food in an upscale restaurant.
Siena Tavern Homemade pasta and pizza in a trendy, River North spot.
Somerset A hot spot for all meals of the day: brunch, lunch, or dinner. The rooftop offers great views of the city!
The Publican A West Loop classic, this spot focuses on inventive seafood and pork dishes.
Smoque Popular BBQ spot. Try the brisket and pulled pork!
The Smith Casual River North spot, great for after work drinks and bites or a boozy brunch.
DRINK
Ballast Point Brewing Chicago Sports bar in the West Loop with excellent Cali-inspired bar food and 40+ beers on tap.
Blind Barber Handcrafted cocktails and haircuts plus a grilled cheese menu? This is a one stop shop!
Butch McGuires Iconic bar on Rush Street known for its late night shenanigans with a bit of a younger crowd. Visit over the holidays to admire the festive, holiday decor.
Cindy’s Cocktail bar overlooking Millennium Park and Lake Michigan.
City Winery There are two locations in the city but we prefer the Riverwalk location. The wine menu is massive and the location is a perfect spot for a drink while enjoying the surrounding views.
Drumbar Roof-top bar in the Raffaello Hotel with a chill atmosphere and seasonal cocktails.
Kaiser Tiger Nice patio for warmer temps in a super, relaxed environment. Expect board games and a variety of beers on tap.
Lazy Bird Cozy, speakeasy in the Hoxton Hotel.
LH Rooftop Atop the London House Hotel, this rooftop bar is another great spot for good views and drinks.
Signature Room at the 95th Located on the 95th floor of the Hancock building, this is an upscale spot for city views. Stop by for a drink or stay for formal dinner.
The Aviary Experimental Cocktail bar in the West Loop. This spot is from the same owners of the famous Alinea restaurant, so expect science-experiment -like cocktails ($$!).
Tao Posh nightclub and high-end Asian restaurant. Casual-elegant attire required.
PLAY
Architecture River Cruise Take in views of Chicago’s beautiful buildings alongside insider information from an expert guide.
Art Institute of Chicago For some culture, check out the impressive exhibits at the Art Institute of Chicago. This incredible museum houses more than 300,000 artworks from every era.
Chicago Riverwalk Take a leisurely stroll, grab a drink and soak in the city. This is also the spot to rent kayaks on the river!
Millennium Park A modern, gathering spot in the heart of the city. Don’t miss the famous “bean” sculpture. Check the website for their free summer concert series!
Museum of Contemporary Art Chicago’s contemporary art museum has a variety of ever-changing exhibits.
Magnificent Mile Chicago’s main shopping street where you can find all major brands.
Shedd Aquarium Home to over 32,00 animals from the Caribbean reef to Arctic waters, this is an excellent indoor spot for a rainy day. To avoid crowds, go during the week or early Sunday morning.
United Center Depending on your season of travel, check out a Bulls (basketball) or Blackhawks (hockey) game!
Wndr Museum A fun, playful museum that boasts interactive walk-through exhibits. An insta-dream.
Skydeck Chicago A clear observation deck on the tallest building in the western hemisphere, the Skydeck has awesome views of the city skyline. Buy tickets in advance.
North side: lincoln park, Old town, Wrigley
EAT
Annette’s Friendly neighborhood ice cream shop.
Cafe Ba Ba Reeba A great spot for a Spanish tapas-style dinner before a night out.
Chicago Bagel Authority Steamed bagel shop for delicious breakfast on the go!
Nookies Too Family-owned diner serving all-day breakfast.
Old Pueblo Cantina Authentic northern Mexican cuisine with house-made tortillas and tasty margaritas.
Summer House Santa Monica Modern American dishes in a beautifully curated spot with sunny Cali vibes.
Toast Great spot for a casual, no frills brunch, serving American classics.
Stella Barra A simple, yet chic pizzeria in Lincoln Park. Try the fresh burrata and the crispy calamari.
Drink
Kingston Mines Drink and be merry at the city largest and oldest operating blues club which offers live music daily.
PLAY
Get your sweat on at Core Power Yoga or Flywheel Sports.
Lakeview Trail The perfect spot to beat jetlag with some exercise. This 18 mile Lakefront trail runs from the north of the city to the south. The best views of the Chicago skyline can be seen at the North Ave Beach.
Lincoln Park Zoo Take a walk and visit some of your favorite animals at Lincoln Park Zoo. Admission is free!
North Avenue Beach Great way to spend a summer day, soaking in the sun and city views.
Second City Where many famous SNL names got their start. See a comedy show in this club open seven nights a week.
Shopping on Armitage This street in Lincoln Park has a variety of boutique shops. Expect to find everything from clothing, cosmetics, jewellery, home goods, etc.
Wrigley Field Catch a Cubs’ game and grab a famous Chicago-style hotdog at one of baseball’s most historic parks. Even if you do not have tickets, the neighborhood is super lively on game days.
Wicker Park
EAT
Etta Famous for its’ wood-fired dishes, this neighbhorhood staple has a variety of rich and flavorful dishes. We loved the shrimp and wild mushroom pizza.
Small Cheval Sister restaurant to Au Cheval. Delicious burgers!
Parsons Craving fried chicken? Look no further. This unpretentious spot in Logan Square hits the spot with delicious comfort food.
Drink
Big Star A summertime favorite and one of the best patios in Chicago. A casual, fun atmosphere to enjoy authentic margaritas and tacos.
STAY
Chicago is full of major hotel chains and airbnbs. If you are here for a weekend with limited time to explore the major sites, we recommend staying in the River North/Gold Coast area or the West Loop. Some of our favorite, residential neighborhoods include Lincoln Park, Old Town, Wicker Park and Lakeview/Wrigley. Popular hotel options include the Chicago Athletic Association, W Chicago, Hoxton, and Soho House Chicago.
