Chicago Activities

We are so excited to have you visit Chicago, the city where we first met and which we have made our home! Chicago is a fantastic city, with world class museums, restaurants, shopping, and sports. A weekend isn’t long enough to see everything the city has to offer, so we decided to list some of our favorite activities and neighborhoods below.

The Loop

The Loop is Chicago’s central business district and a large part of downtown. If you want to visit a museum or get a picture in front of The Bean, this is the place to start. 

The Art Institute of Chicago: Chicago’s main art museum and one of the best in the country. The Art Institute’s unbelievable collection of Impressionist, American, Modern, and Contemporary art makes it a must visit (plus, a fun game is to see how many paintings were featured in Ferris Bueller’s Day Off). 

The Bean: Located right next to the Art Institute in Millennium Park, this sculpture by Anish Kapoor is a symbol of the city and one of Chicago’s most insta-worthy locations. 

Willis (Sears) Tower Observation Deck: Take an elevator to the top of the second tallest building in the country and get a bird’s eye view of Chicago and Chicagoland.

River North and The Magnificent Mile

River North and The Magnificent Mile are located across the river from The Loop and make up the other half of downtown Chicago.

Chicago Riverwalk: Take a walk along the Chicago River, which has tons of access points along Wacker Drive. During your walk, grab a drink at City Winery. 

If you’re itching for even more steps, continue north up the Magnificent Mile (N. Michigan Avenue), Chicago’s premier shopping street.

For the extremely ambitious 20K+ step crowd, you can take the Mag Mile to Oak Street Beach, which will put you on Chicago's Lakefront Trail, an incredible 18-mile paved path along the Lake Michigan shoreline.

For lunch, we recommend checking out Ema (one of our favs) or Mr. Beef, a neighborhood hole in the wall that's been serving Italian Beef for decades (fans of The Bear, you might recognize it!).

Finally, we would be remiss not to mention Washington Square Park, the ultimate place to sit on a park bench and see so many cute dogs wearing jackets.

West Loop and Fulton Market

West Loop and Fulton Market comprise Chicago’s dining hotspot and its Michelin Guide center. We won’t list any Michelin starred restaurants, but if you’re interested in food, this neighborhood is worth a visit. 

The Hoxton Hotel: The Hoxton is home to two bars (Cira and Lazy Bird) and one of Stephanie Izard’s legendary goat-themed restaurants, Cabra. Our first date started with a drink at Lazy Bird and ended with goat empanadas at Cabra, so both spots are some of our favorites. 

Monteverde: Monteverde is Jon’s favorite restaurant and he insists this list wouldn't be complete without it. Note that the competition for reservations is fierce, though, so we recommend acting fast if you’re interested!

Lincoln Park and Lakeview

Lincoln Park and Lakeview are the two neighborhoods just north of downtown, easily accessible from the Red, Purple, or Brown L lines. These two neighborhoods give a nice idea of what living here actually looks like. 

Lincoln Park: Chicago’s largest park, perfect for a nice walk or a post-Farmer's Market picnic.

Lincoln Park Zoo: It’s free! And better than San Diego.

Diversey: Our new hood! If you can make it up to the Diversey Brown Line stop, we highly recommend taking a bottle of wine to a neighborhood BYOB restaurant—our all-time favorite is D.Cuisine.

Wrigley Field and Wrigleyville: Located in Lakeview, Wrigley is the home of the Chicago Cubs and center of Chicago sports. Visit Wrigley Field and follow up with a session in the batting cages at Sluggers.