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6 Fun Things to Do in Chicago for Couples

9/27/2023

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Planning a fun couples weekend away in Chicago? I've rounded up my favorite things for couples to do in Chicago!
Fun Things for Couples to Do in Chicago
Disclosure: some of the links below are affiliate links. If you purchase a linked item, I will make a commission, at no extra charge to you. As an Amazon Associate, I earn from qualifying purchases.

Planning a couples getaway to Chicago?

My husband and I have been taking marvelous trips up to Chicago for couples trips for at least a decade. Over the years, we've rounded up a few of our favorite fun things to do for a date night in Chicago! And while you're here, don't forget to check out my other resources on spending time in The Windy City!
  • What to Wear in Chicago in September and October
  • {Hotel Review} The Viceroy, Chicago
  • {Hotel Review}, The Drake Hotel, Chicago
  • 8 of the Best Midwestern Road Trips

6 Fun Things to Do in Chicago for Couples

Lunch at The Ralph Lauren Restaurant

Snag a tasty, traditional American lunch at RL Restaurant, Chicago, a celebrity haunt for decades. Located on the northern end of Michigan Avenue, across from the Water Tower, in the Ralph Lauren Store, you'll enjoy their takes on classics (hamburgers, crab salad, delicious, spicy Bloody Mary's).
The Ralph Lauren Store & Restaurant, Chicago. Fun Things for Couples to Do in Chicago

Classy Shopping in the Gold Coast

Keep venturing north and you'll find the best shopping in Chicago in the Gold Coast. Hermes, Jimmy Choo, Christian Louboutin, COS, St. John, Golden Goose - you name, it, they have it up here!
Chicago Gold Coast Shopping Fun Things for Couples to Do in Chicago
Photo credit: Choose Chicago

Drinks at Gibsons

Grab a drink at Gold Coast staple, Gibson's Chicago. Keep the husband interesting by reminding him that it's the site of the weekly drinking sessions that happen throughout The League.
Gibson's, Chicago. Fun Things for Couples to Do in Chicago
Photo credit: Gibson's Chicago

Architectural Boat Tour

Architectural Boat Tour, Chicago Fun Things for Couples to Do in Chicago
My *favorite* couples activity in Chicago is, without a double, an architectural boat tour. Take in Chicago's stunning buildings from a new angle and enjoy a cocktail while you learn slightly more than you really wanted to know about architectural styles and the history of the Windy City. The are many vendors. Be sure to buy directly from the provider to save money on unnecessary processing fees.

Explore The Art Institute of Chicago

The Art Institute of Chicago Fun Things for Couples to Do in Chicago
One of the best art museums in the world, The Art Institute of Chicago, is worth an entire afternoon. And don't skip the Thorne Miniature Rooms, my favorite exhibit, featuring tiny, stunningly accurate depictions of historic and famous rooms from around the world throughout history.

See a Show

The Art Institute of Chicago Fun Things for Couples to Do in Chicago
Hop to the southern side of the Chicago River and take in a show at one of the city's historic theatres! We've see Book of Mormon & Trevor Noah, to name a few.

Thanks for stopping by!

The Bean, Chicago, at night. Fun Things for Couples to Do in Chicago
I hope you have a fabulous trip to Chicago! Let me know your Chicago date night ideas!

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Fun Things to Couples to Do in Chicago
Fun Things for Couples to Do in Chicago
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