Big List of Date Ideas for Chicago Summer 2024

May 24, 2024

I like to try to be outside in the summer! Day or night, we try to get some date nights in. Manny and I often split our date nights or day dates between going to our favorite restaurants and bars and exploring new spots. Sometimes it’s the hardest decision! We love having Summer date nights, but there is SO much we want to do and see in Chicago. Here’s my grand list of ideas for Summer 2024!

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. Some of the big names this year are John Legend, Charlie Puth, Ms. Lauryn Hill, Jason Mraz, Carrie Underwood, Counting Crows, Ne-Yo, and Santana.
  • The Salt Shed – this new concert venue opened last year and is becoming one of my new favorites! The venue is super cool and even if you can’t make it to a concert, Eeeeeatsacon is a fun foodie event we went to last summer – another fun day date (but you can bring the kids too!)
  • 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. Initially, I was thinking of going to the Sinatra evening!

Indoor Things

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

  • Gatsby Speakeasy – this is so fun and right now they have an Alice and Wonder cocktail theme!
  • Art Institute – Stop by the cute cafe that overlooks a garden! Check their free days too.
  • Wine Tasting – I did this with friends but can be done for a date too! It’s an urban winery and they make all the wine onsite! One of the very few wineries in Chicago. There’s a Groupon deal under $40 for a bottle, tasting and a small tour!

Outdoor Things

  • 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!
  • Have a boogie lunch at Miru – this is not cheap but the views are amazing! Definitely special occasion spot. See the reel here.
  • Take the Metra to Downtown Lombard and do some exploring! We had so much fun doing this. See our day here!
  • Take Chinatown tour – see this reel from our day date in Chinatown!
  • Visit Mario’s Italian Lemonade in Little Italy – another Chicago classic! There may be a line, but it goes quick! Talk a walk through Little Italy after.
  • City Winery Riverwalk Wine Garden + Sweet Home Gelato – you can’t go wrong with this classic Chicago date!
  • The Sights & Sips Cruise on the Chicago River – this is more splurge-worthy date, but it includes actually getting on the water! Tickets include a 2-hour cruise, hors d’oeuvres, cash bar, and a guaranteed table.


  • Get a Fireworks Room at the Sable at Navy Pier – this package includes a room perfect for fireworks viewing, specialty chocolates, late check-out, and evening cocktails. This would be perfect for a special summer birthday or anniversary!
  • 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.

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


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