10 Second Date Ideas in Chicago

See the city up close through the Chicago Architecture Center's walking tours, with themes including Gold Coast Astor Street, River North, and Northwestern University. The architecture hub also offers a river cruise aboard First Lady.

The center is open until 5pm Sunday through Thursday and until 7pm on Fridays and Saturdays.

Take a second date one gallery at a time at the Art Institute of Chicago. Join a free guided tour in English at 1pm or 3pm daily, or use the self-guided "What to See in an Hour" tour on your phone for a shorter visit.

The museum is closed Tuesdays and stays open until 8pm on Thursdays.

Laugh together through a revue at The Second City, a comedy theater in Old Town. Original sketches and songs include improv, so each night is different, and there is no food or drink minimum.

General admission seating is at cabaret-style tables with your own party. Bring a jacket, since the room can be cold. The Mainstage show starts at 8pm.

Settle into dinner at Penumbra, a dimly lit wine bar and steakhouse in Logan Square. Choose from wines by the glass or a longer bottle list alongside steaks, seafood, and vegetarian dishes.

Come on a Wednesday between 5pm and 6:30pm and wine by the glass costs half price. Dinner begins at 5pm Wednesday through Sunday evenings, with online booking available.

Explore a changing contemporary American menu at Sepia, a Michelin-starred restaurant in the West Loop. What lands on your plate changes with the evening, from wagyu beef tri tip to lemon doughnuts.

The bar program and wine list, including hard-to-find bottles, give you something to sip between courses. The four-course prix fixe costs $125 per person, with reservations available online.

Dine in low light among ornate furniture and vintage-style art at Ciccio Mio, an Italian supper club in River North.

We'd choose the spicy vodka rigatoni or lasagna rolls, followed by cannoncini for dessert. Reservations open online 21 days ahead at 9am and fill quickly, though a couple of tables are held for walk-ins.

Keep a second date relaxed with a free Chicago Riverwalk stroll and stops for wine or a bite. The 1.25-mile route runs from Lake Street to the lakefront through The Confluence, The Arcade, The Civic, and the Esplanade.

Look for public art, including ART on theMART, along the way. Path hours are 6am to 11pm, with no reservations needed.

At Koval Distillery, you walk the production floor past copper pot stills, then settle in for a guided tasting of three spirits.

The Classic Tour runs Saturday at 1pm and Sunday at 2pm, and the Whiskey Tour runs Saturday at 3pm. Each lasts 45 minutes and costs $12 per person. Book online, since weekend tours can sell out. Tastings are for ages 21 and over; hands-on cocktail classes lasting about 90 minutes offer another option.

Have a drink somewhere with character at Forbidden Root, a West Town brewpub in a remodeled old theater with steampunk light fixtures.

A hidden TV appears only for Chicago playoff games, leaving the room focused on conversation the rest of the year.

Hear live music any night at Empty Bottle in Ukrainian Village, where all shows are for ages 21 and over. Most Mondays bring free performances by local and touring acts, so you can discover a band together without paying for a show.