Summer is hard to get out just us two. The kids are home and our schedule is much more inconsistent than the school year. So we try to squeeze in a few hours here and there, even if it’s midweek or midday. Day or night, we try to get some date nights in. I’ve added lots of summer things to do – more than just going out to a restaurant. So here is the big list of date ideas for Chicago summer 2025!

Live Music

There’s just something about enjoying live music with your favorite person! Obviously, Lollapalooza is the biggest concert every Chicago summer, but here are my top picks for a more intimate, unique experience!

• Jazzin’ at the Shedd – your ticket includes a jazz performance on their terrace and admission to the full aquarium after hours. This is definitely a more 21+ event and SO cool! Jazzin’ at the Shedd occurs most Wednesdays with entrance times between 5:00-6:30 pm. Grab dinner before 8:00 pm and dance with the dolphins until 10 pm.
• Ravinia Festival – Making the trek to Ravinia, in Highland Park, is a must-do in your Chicago lifetime! Pack a picnic or order from the multiple restaurants in the park.
• The Salt Shed – The venue is super cool and even if you can’t make it to a concert, they do have lots of events and markets going on all summer.
• Tuesdays on the Terrace – this is another museum event more geared to the 21+ crowd. Every Tuesday, the MCA hosts a free music concert in their terrace garden. Pack a snack or buy from their bar. Capacity is limited so make sure to reserve your spot in advance!
• Concerts Under the Stars at Aire – this sounds so romantic and tickets are selling fast! Aire is the rooftop bar at the Hyatt Centric in the Loop with amazing city views. Use code CHICAGOGOODLIFE10 for 10% off!
• Vinyl night at the Park Hyatt (I know not live music, but still music themed!)

Indoor Things

For those days where you just want some really good air conditioning…

• Play Board Games – we love this spot + food/drinks are good too. See the reel here!
• Arcade – Elston Electric is a new arcade at Salt Shed. They have many old school pinball machines.
• Art Institute – Stop by the cute cafe that overlooks a garden! Check their free days too.
• Wine Tasting – It’s an urban winery and they make all the wine onsite! It’s a very small winery, but cool they make it all there. One of the very few wineries actually in Chicago. There’s a Groupon deal under $40 for a bottle, tasting and a small tour! Check out other breweries along Malt Row too!

Outdoor Things

• $5 dollar White Sox game night!
• Spend the day in Pilsen! Check out the National Mexican Art Museum (free to enter)! See the itinerary here.
• Rent bikes along the lakefront! I also have a free unlock. Pack a picnic too!
• Art on the Mart – The “World’s largest digital art platform” projects contemporary art onto the facade of the massive Merchandise Mart building. The best spot is the Chicago Riverwalk Jetty between Wells and Franklin Street. Pack a picnic and grab a beer from The Northman Beer & Cider Garden and enjoy the show!
• Movies in the park at Millennium Park – BYO food and drinks!
• Spend the day in Chinatown – see this reel from our day date in Chinatown!
• Visit Mario’s Italian Lemonade in Little Italy – another Chicago classic! Talk a walk through Little Italy after.
• City Winery Riverwalk + Sweet Home Gelato – you can’t go wrong with this classic Chicago date!

Fireworks

• Have dinner at Reunion at Navy Pier and then watch the fireworks from the restaurant!
• Fireworks Kayak Tours – I would love to try this! We’ve kayaked the river at night before and it’s so cool!
• Roberts Pizza and Dough Co. – right on the river, have dinner and drinks and watch the show! One of my favorite spots.

Street Festivals

You can see some of the 100’s of street festivals here in our summer bucket list.

Some Burbs things to do

• Head out to Woodfield mall! They have a few games and arcades, then see a comedy show. You can see out day here!
• Kayak the Skokie Lagoons and walk along the trails. Bring a picnic and some folks even fish.
• Visit Vivid Creatures at the Morton Arboretum – these were really cool. You can also mini-golf too at Wonder Woods.

Hopefully you find a little something for you and your partner!

Christine