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Date Ideas in Chicago

Chicago offers an incredible range of date experiences, from architectural boat tours on the river to cozy jazz clubs in the winter. The city's world-famous food scene, stunning lakefront, and vibrant arts community mean there's always something new to try. NextWeekend helps Chicago couples find the right activity for any season or weather condition.

Popular Activities for Couples in Chicago

Lakefront TrailArchitecture toursDeep-dish pizzaJazz clubsMillennium ParkNavy Pier

Best For

Foodies
Architecture fans
Winter romantics
Music lovers
Couples dating in Chicago

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Frequently Asked Questions About Dating in Chicago

What are good date ideas in Chicago?

Great Chicago date ideas include an architecture boat tour, walking the Lakefront Trail, trying deep-dish pizza at a classic spot, visiting the Art Institute, and catching live jazz in the evening.

What are winter date ideas in Chicago?

Winter dates in Chicago include ice skating at Millennium Park, visiting the Christkindlmarket, warming up at a speakeasy, exploring the Museum of Science and Industry, or catching a comedy show at Second City.

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