Date ideas in Chicago: 15 ideas for every season

• Budgetfree
• Best forfirst date
• Time1 hour
• WhereMain Branch of the Chicago River, the Loop

The Riverwalk runs along the south bank of the river through downtown, below the bridges and right next to the water. You get skyscrapers on both sides, boats gliding past and plenty of benches and terraces to sit down. It's lively without being loud, which is ideal for a first conversation.

Tip: Walk from the lake end toward the west and look up at each bridge as you pass. In warm months, the Riverwalk has spots for a drink by the water.

• Budgetfree
• Best forfirst date, sightseeing
• WhereMichigan Avenue, the Loop

Cloud Gate, the mirrored sculpture everyone calls "the Bean," reflects the skyline and anyone standing beneath it. Nearby, the faces on Crown Fountain spit water in summer, and the Lurie Garden is a quiet corner of flowers. It's a classic for a reason and a fun place for a first photo together.

Tip: Go early in the morning or later in the evening to avoid tour groups. In summer, check the free concert schedule at the Pritzker Pavilion.

• Budgetfree
• Best forfirst date, any weather
• WhereMichigan Avenue and Washington Street

The Chicago Cultural Center is a free public building with one of the largest Tiffany glass domes in the world. Exhibitions, concerts and that glowing ceiling make it a surprising first date stop, and it's directly across from Millennium Park.

Tip: Pair it with Millennium Park as a mini tour. Lie back on a bench and look up at the dome together for a minute without talking. It's more romantic than it sounds.

• Budgetmedium
• Best forsecond date, visitors
• Timeabout 90 minutes
• WhereChicago River, downtown

Several operators run architecture tours on the Chicago River, and the best ones turn the skyline into a series of stories: the fire of 1871, the race for height, the towers that broke the rules. Even locals learn something, and you'll leave with dozens of conversation topics.

Tip: Choose a sunset departure if one is offered and sit on the open top deck. Cruises usually run from spring to fall.

• Budgetfree to low
• Best foractive, summer
• Timehalf a day
• Wherealong Lake Michigan

The Lakefront Trail runs for miles along Lake Michigan, past beaches, harbors and parks with the skyline always in view. Renting bikes and riding a stretch together is active, scenic and gives you lots of natural stops for a break.

Tip: Ride north toward North Avenue Beach and stop for a swim or a cold drink on the sand. Weekday evenings are calmer than weekend mornings.

• Budgetfree
• Best forromantic, evening
• WhereHyde Park, South Side

This small peninsula in Burnham Park sticks out into the lake and has one of the most beautiful views of the skyline from the south. Stone steps lead down to the water, and in summer locals picnic on the lawn. It's the kind of place that feels like a secret even though it isn't.

Tip: Bring a blanket and food to share. Combine it with a walk through Hyde Park and the University of Chicago campus.

• Budgetmedium
• Best forplayful, visitors
• WhereNavy Pier, Streeterville

Navy Pier stretches into Lake Michigan with the Centennial Wheel at its heart. Its enclosed gondolas climb high above the lake for a slow loop with views of the shoreline and skyline. It's touristy, but a Ferris wheel at dusk with the right person is still a good idea.

Tip: In summer, Navy Pier usually has fireworks on some evenings. Walk to the very end of the pier for the best view back at the city.

• Budgetfree to low
• Best forwinter, rainy day
• WhereGarfield Park, West Side

One of the largest conservatories in the country, Garfield Park Conservatory is full of palms, ferns and desert plants under glass. Stepping in from a snowy street into warm, humid air feels like a short trip to somewhere tropical, and the quiet paths are perfect for talking.

Tip: Check the website for current entry rules and reservations. Bring a layer you can take off, it gets warm inside.

• Budgetmedium
• Best forrainy day, second date
• WhereMichigan Avenue, the Loop

The Art Institute of Chicago is one of the great museums in the world, home to famous works like Seurat's "A Sunday on La Grande Jatte" and Hopper's "Nighthawks." For a date, choose one wing and take your time rather than racing through.

Tip: Each of you secretly picks the painting you'd take home and reveals it at the end. Illinois residents sometimes get free days, so check the website.

• Budgetfree
• Best forrelaxed, any season
• WhereLincoln Park, North Side

Lincoln Park Zoo is one of the oldest zoos in the country and free to visit. Watching animals together is easy, playful and gives you something to talk about without trying. The Lincoln Park Conservatory next door adds a warm greenhouse for colder days.

Tip: Make a small bet: whoever spots a specific animal first picks where you eat afterwards. Then walk to the lake at North Avenue Beach.

• Budgetlow to medium
• Best forsecond or third date
• WhereBroadway, Uptown

The Green Mill has been open in Uptown since 1907 and is one of the most famous jazz lounges in the country. Dark booths, an old bar and live music most nights make it feel like stepping into another decade, without any dress code drama.

Tip: Arrive early on weekends to get a booth. Respect the "no talking during sets" vibe and save the conversation for the breaks.

• Budgetmedium
• Best forsecond date, fun
• WhereOld Town

The Second City has launched the careers of many famous comedians since 1959. An evening of sketches and improv gives you a shared laugh and plenty to quote on the walk home through Old Town.

Tip: Book ahead on weekends. Avoid the front row unless you're both happy to become part of the show.

• Budgetmedium
• Best forsummer, sports fans
• WhereWrigleyville

Wrigley Field is one of the oldest ballparks in Major League Baseball, with ivy on the outfield walls and a neighborhood that buzzes on game days. A baseball game is relaxed enough to talk through and exciting enough to share a few high fives.

Tip: Even if you aren't big fans, an afternoon game in summer is a great date. Wear the right cap or none at all, the Cubs and White Sox rivalry is real.

• Budgetfree
• Best forrelaxed, any season
• WhereWicker Park, Bucktown and Logan Square

The 606 is an elevated trail on an old railway line that runs through several neighborhoods on the Northwest Side. You can walk it end to end or drop down into Wicker Park and Bucktown for coffee, record shops and vintage stores.

Tip: Plan your route so you end in Wicker Park. Each of you picks one shop to pop into along the way.

• Budgetlow to medium
• Best forwinter, festive
• WhereDaley Plaza and Lincoln Park Zoo

The Christkindlmarket in Daley Plaza is inspired by German Christmas markets and usually runs from late November until Christmas Eve, with mulled wine in collectible mugs. Lincoln Park Zoo usually lights up for ZooLights during the same season. Add skating on the ribbon at Maggie Daley Park and you have a full winter date.

Tip: Weeknights are calmer. Keep the mug as a souvenir of your first winter date.