10 Chicago Spring Date Ideas we love for all budgets
May 13, 2025
Spring in Chicago is finally here—and after months of freezing temps and staying indoors, it’s time to get out and enjoy the city again. Whether you’re going on a first date or just looking for something new to do with your partner, there are tons of fun ways to take advantage of the warmer weather. From grabbing ice cream by the lake to catching a game or checking out a street fest, here are some easy, laid-back date ideas that’ll help you make the most of spring in the city.
Food & Drinks
Malt Row Crawl
For all the beer lovers out there, create your own beer crawl! Malt Row in Ravenswood is home to a ton of craft breweries, an award-winning distillery, and a winery! We did Dovetail, Begyle, Forbidden Root and Koval (which is dog and family-friendly + they have a brand new space) This area is super walkable and accessible from the Brown Line. You can end the day at Spacca Napoli, which has some of the best wood-fired pizza! Check their official guide here!
We did a food crawl date night for our wedding anniversary through Albany Park recently and went to so many great spots to enjoy food from all over the world! It was the perfect spring date night in Chicago! Here’s our round-up: Subo Flipino Kitchen, Hot Dog Station, Cilantro Taco House – Mexican, Pisco Peruvian, Antepli Turkish Gourmet for desserts, Lindo Michocan – Mexican, Atitlan Restaurant – Guatemalan, Dulce De Leche Cafe – open until 4pm, great for brunch and coffee!
I would also stop in at Bokeh for some cocktails and mocktails! They are amazing!
Entertainment
We sawArt by Remy Bumppo Theatre at Theatre Wit, and WOW — what a smart, funny, and heartfelt ride. Three longtime friends, one $200K modern art painting, and a whole lot of sharply written banter that had the whole audience laughing and thinking. It flew by at just 80 minutes with no intermission — we could’ve watched these three talk for hours. Highly recommend this for a night out — and bonus: tickets are only $17 on Hot Tix this weekend (normally $40)! Theater Wit is walkable from both the Belmont Red/Brown/Purple and Southport Brown Line stations, with tons of great spots for dinner nearby.
If it’s raining outside, play ping pong at Ace Bounce (really great happy hour deal) or the newly opened Electric on Elston! They have a lot of old school games and the space is really cool.
Another rainy spring day is the new Vinyl Sundays at the Park Hyatt! You can a Side A/B cocktail to match the theme of the Vinyls. it’s a cool concept for any music, vinyl lovers out there.
Arts
Pilsen is one of our favorite neighborhoods for the food and culture! When it’s a nice spring day, take a walk to see all the street murals, explore the National Museum of Mexican Art, and then have dinner at 5 Rabinitos or La Mejikana. There is a such good shopping too. The vintage shop on 18th is amazing. End the night at a nightcap at La Luna or Del Toro. I have a whole itinerary that includes a day in Pilsen here if you want even more ideas!