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Things To Do

We’re so excited to share some of our favorite spots in Chicago with you!

Chicago Riverwalk

Chicago Riverwalk, Chicago, IL 60601

A beautiful spot for a walk, drink, or bite to eat along the water. Grab a glass of wine, rent a kayak, or simply enjoy the views of Chicago’s iconic architecture.

Chicago Architecture River Cruise

112 East Wacker Drive, Chicago, IL 60601

Lane and William highly recommend! These tours offer a fun and fascinating look at the city’s skyline from the river.

Gibsons Italia

233 North Canal Street, Chicago, IL 60606

A delicious Italian restaurant on the River. Also where William asked Lane’s parents for their blessing to marry her!

Mr. Beef

666 North Orleans Street, Chicago, IL 60654

Where the show "The Bear" takes place, offering another iconic Chicago dish: the Italian Beef sandwich.

Millennium Park

201 E. Randolph Street, Chicago, IL 60602

Stroll through Millennium Park, snap a photo at “The Bean,” and enjoy the gardens, fountains, and public art in the heart of downtown.

The Art Institute of Chicago

111 South Michigan Avenue, Chicago, IL 60603

One of the best art museums in the world, home to classics like American Gothic and Nighthawks.

Shedd Aquarium

1200 South DuSable Lake Shore Drive, Chicago, IL 60605

Dive into one of Chicago’s most iconic attractions, home to over 30,000 aquatic animals from around the world.

Lakefront Trail

Rent a bike, join William for a run, or take a scenic walk along Lake Michigan for some fresh air and gorgeous views.

Lou Malnati's Pizzeria

410 North Michigan Avenue, Chicago, IL 60611

No trip to Chicago is complete without trying the city’s iconic deep-dish pizza. There are plenty of great spots around town, but Lou Malnati’s is our personal favorite!

Oak Street Beach

Chicago, IL 60611

Yes, we have a beach in Chicago :)

LUXBAR

18 East Bellevue Place, Chicago, IL 60611

A lively brunch spot in Chicago’s Gold Coast neighborhood.

Hopsmith Chicago

15 West Division Street, Chicago, IL 60610

Where Lane spent way too many nights during her Chicago days.

Butch McGuire's

20 West Division Street, Chicago, IL 60610

A true Chicago classic! William highly recommends the Guinness.

Shopping on Armitage Avenue

912 West Armitage Avenue, Chicago, IL 60614

Lane’s old neighborhood! Great shopping, cafes and restaurants!

Kincade's Bar & Grill

950 West Armitage Avenue, Chicago, IL 60614

A charming sports bar in Lincoln Park where Lane’s parents met!

Summer House Santa Monica

1954 North Halsted Street, Chicago, IL 60614

A great brunch spot in Lincoln Park. Also where William met Lane’s parents for the first time.

The Second City

230 West North Avenue, Chicago, IL 60614

This legendary comedy theater has launched the careers of icons like Tina Fey, Steve Carell, and Bill Murray—and it’s still cranking out sharp, smart, and hilarious sketch and improv shows every night.

Aba

302 North Green Street, Chicago, IL 60607

Delicious Mediterranean food in the West Loop neighborhood.

The Wiener's Circle

2622 North Clark Street, Chicago, IL 60614

Although the staff may not be the friendliest, the Chicago style hotdog is a must!