Big List of Date Ideas for Chicago Summer 2023

May 28, 2023

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 2023!

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.
  • Live at Lighthouse: Summer Series – this is a new concert series at the beautiful Lighthouse ArtSpace and it sounds so cool! Of the six different immersive performances, the one I would pick would be Allan Harris, a Harlem-based vocalist, guitarist, bandleader and composer, performing on July 13. Pair it with dinner at The Vig before or after!
  • 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! Upcoming concerts include Nickel Creek, Jenny Lewis, Le Tigre, Trombone Shorty, and Guster with Neko Case.
  • 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, but they just added two Lizzo/Beyonce shows, too! Definitely go to the later show to get the full experience!
  • Hyde Park Summer Fest – The Hyde Park Summer Fest is a ticketed event running June 17-18 at Midway Plaisance Park. Big-name acts this year at 2 Chainz, Clipse, and Lil’ Kim! Manny and I are going with some college friends this year, can’t wait!

Indoor Things

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

  • Art Institute – The new Van Gogh exhibit is only here for the summer and the Gio Swaby pop-up closes July 3, so we gotta get over there for a quiet, chill day date!
  • Color Factory – I know this seems like it would be a family event, but both times I’ve been, I’ve seen couples exploring the interactive museum and it just looks so cute and fun to do without the munchkins dictating how fast or slow we go. 🙂 Use my code GOODLIFE for 20% off!
  • Visit Mario’s Italian Lemonade in Little Italy – another Chicago classic! There may be a line, but it goes quick!

Hang along the Riverwalk


  • 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!
  • 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!

Street Festivals

There’s approximately 2,784 festivals you can attend this year in Chicago but these are the ones that I think are the most date-worthy!

Dinner and a Show

  • West Side Story + Alla Vita – for a super fancy night out, head to the gorgeous Alla Vita for an Italian dinner and then to the Lyric Opera House to see West Side Story.
  • Improv at iO Theater + Summer House Santa Monica – you can’t NOT have fun at an iO improv show! They have a ton of different series, but I’m definitely interested in the Satirical Race Theory show playing on Saturdays! Summer House Santa Monica has a great airy space and is walkable to and from the theater!
  • Movies at Gallagher Way – Choose a restaurant like Big Star, Smoke Daddy, or Swift & Sons and then enjoy a movie on the big screen! I’d love to see Clueless or Top Gun: Maverick there!

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


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