Things to Do in Chicago for Couples: Easy Date Plans for Two

Daytime dates

Lincoln Park Zoo

Neighborhood: Lincoln Park (2400 N. Cannon Dr.) · Cost: no admission (parking $35–45 a day) · When: gates 8am–5pm daily, buildings 10am–4:30pm

Open every day of the year, and easy to make into a two-hour plan with no pressure: wander, pick a favorite animal, keep walking. Tip: take the bus or bike, since parking is the main expense.

Art Institute of Chicago

Neighborhood: the Loop (111 S. Michigan Ave.) · Cost: $32 adults, $20 for Chicago residents with proof of address · When: 11am–5pm, until 8pm on Thursdays; closed Tuesdays

Pick one gallery each and show each other your favorite piece. A Thursday visit runs into the evening, and Illinois residents can visit without charge on third-Thursday evenings from 5pm to 8pm (check the museum's site for the current schedule). Tip: bring an ID or bill with your address for the resident price.

Chicago Cultural Center

Neighborhood: the Loop (78 E. Washington St.) · Cost: no admission · When: daily, 10am–5pm

A quick, beautiful stop under the Tiffany glass dome, and a central place to meet before heading anywhere else downtown. Tip: check the exhibitions page and pick one show to see together.

Make something together

The Chopping Block

Neighborhood: Lincoln Square (4747 N. Lincoln Ave.) · Cost: varies by class, plus a 15% administrative fee · When: see the class calendar

Hands-on classes put you in a small team of three to five that cooks the full meal and then eats it together, so you'll probably share your station with another pair or two. There are demonstration classes too if you'd rather watch a chef and taste, plus wine and cocktail classes. Tip: a cooking class makes a great double date, since four of you can share a team.

Evening dates

Music Box Theatre

Neighborhood: Lakeview (3733 N. Southport Ave.) · Cost: tickets vary by show · When: see the calendar; weekend matinees

A 1929 movie palace with a twinkling, star-covered ceiling and a red velvet curtain, showing independent, foreign, cult and classic films. The theatre's own history page mentions the first dates that have happened under its starry sky. Tip: on Friday evenings and before the first weekend shows, the house organist usually plays before the film.

Andy's Jazz Club

Neighborhood: River North (11 E. Hubbard St.) · Cost: about $20 a person on an average night · When: shows at 6pm, 8:15pm and 10:30pm (no 10:30 show Monday and Tuesday)

A full-dining jazz club where you can have dinner during the set. Reservations are required for every guest and each covers one show, with the reservation time set before the set starts (7:45pm for the 8:15pm show, for example). Tip: no-shows that aren't canceled are charged the full admission, so cancel if plans change.

360 Chicago

Neighborhood: the Magnificent Mile (875 N. Michigan Ave.) · Cost: general admission from $27 for adults online, higher at the gate · When: daily, 9am–11pm

The observation deck on the 94th floor, with the CloudBar on the same floor for a cocktail or mocktail. Go around sunset and watch the city light up. Tip: booking online is cheaper than buying at the gate. If you'd rather see the view from the Loop side, the Skydeck at Willis Tower is open until 8pm most days this winter (9pm Saturdays).

A short note on Valentine's Day

Valentine's Day 2027 falls on a Sunday, so the whole weekend before it will be busy. Book anything with limited seats early: Andy's requires reservations, and The Chopping Block posts its classes on its class calendar. Keep a low-key backup in mind, like the Art Institute, a film at the Music Box or a walk along the lake.

A few things to plan around

• Closed days. The Art Institute is closed on Tuesdays.
• Reservations. Andy's needs one for every guest, and cooking classes fill up on weekends.
• Fees on top. The Chopping Block adds a 15% administrative fee to each class.
• Cheaper online. 360 Chicago's lowest prices are online, not at the gate.

Three easy plans to suggest

Each one fits in an afternoon or an evening:

1. Zoo, then brunch. Lincoln Park Zoo when the gates open, then brunch in the neighborhood.
2. Dinner and a set. A table for the 8:15pm show at Andy's in River North.
3. A film and a walk. An evening show at the Music Box, then a stroll down Southport.

For more ideas, see our guides to things to do in Chicago at night and easy things to do in Chicago this weekend.

Make it a plan with someone nearby

Some date plans are more fun with another couple or a few people who share your interests: a cooking class for four, a jazz set, a walk by the lake. Lighthouse is a social app for meeting people nearby who share your interests. You can see who's around and what you have in common, start an activity you'd like to do as a pair, or join one someone in your neighborhood has posted. Each activity has its own group chat, so you can say hi and agree on the details before you meet.

Good to know

• Check before you go: hours change around holidays, and shows and classes sell out. That goes for anything in this post, too. Each listing links to its official source below.
• Getting there: the Loop and River North spots are near several 'L' lines; the Music Box is three blocks north of the Southport Brown Line stop.
• Prices and bookings are set and handled by each venue.