8 Unique Fall Date Nights in Chicago

August 27, 2023

This blog post comes highly requested on Instagram! I tried to come up with budget-friendly and splurge fall date night ideas around the city! Hopefully, some of these are helpful – I’d love to hear from you. Some are fall-themed, and others are just happening

So here’s my Fall 2023 list of ideas for date nights in Chicago!

Food and Drinks

Celebrate Oktoberfest with a Malt Row crawl

For all the beer lovers out there! Create your own beer crawl or check our Brewer’s Triangle Oktoberfest, which is a beer festival happening a 3 different breweries on September 23rd!

Malt Row in Ravenswood is home to a ton of craft breweries, an award-winning distillery, and a winery! Manny just did this with his friends and had the best time. He did Dovetail, Begyle, 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! There are also plenty of restaurants and shopping in the area. Check their official guide here!

Bloody Mary Fest

Last of the drink date night ideas…..Bloody Mary Fest! It’s one of Manny’s absolute favorite weekend drinks! Bloody Mary Fest returns on Sunday, October 15th to Theater on the Lake. We did this a few years ago and it’s a great event in the beautiful event space on the lake, Lakefront Restaurant. This event will feature a competition where you can sample some of Chicago’s best Bloodies and vote for your favorite. There will also be brunch bites, other brunch cocktails, and an artisan market.

Create your own Albany Park Food Tour

Manny and I did a food crawl date night through Albany Park recently and went to so many great spots to enjoy food from all over the world! It was the perfect date night in Chicago! Here’s our round-up:

  • Subo Flipino Kitchen
  • Hot Dog Station
  • Cilantro Taco House – Mexican
  • Pisco Peruvian
  • Antepli Turkish Gourmet
  • Lindo Michocan – Mexican
  • Atitlan Restaurant – Guatemalan
  • Lawrence Fish Market
  • 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!

Bokeh is a great fall date night spot for cocktails in Chicago


See a Halloween Movie

If you haven’t been to the iconic Music Box Theatre, it’s a Chicago landmark! So much history and they are having their annual 31 days of horror films in October and have lot’s of Halloween movies.

Gallagher Way and Rooftop Cinema in The Emily Hotel will also have fall-themed movies!


Earlier this year I went to WhirlyBall for the first time and it was SO 👏MUCH 👏 FUN 👏. There’s also bowling, bags, a full bar, and lots of delicious food on the menu! This would be such a unique date, especially if it’s a cooler day out!

CLUE Walking Mystery

This interactive experience takes you along downtown Chicago, starting at State Street to play the game, CLUE! Choose your character and find your clues in 90 minutes while walking around the city. Such a fun date idea that doesn’t involve eating or drinking!


Explore Pilsen

Pilsen is one of our favorite neighborhoods for the food and culture! 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. 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!


Open House Chicago

If you have never done Open House Chicago with the Chicago Architecture Center, I highly recommend it! It’s happening October 15th-16th this year. This is your chance to check out buildings and parts of the city that are usually closed to the public and learn its history, etc. It’s FREE & really cool way to explore the city. Many of the sites will indicate if they are family-friendly, accessible, etc. This is awesome for tourists and residents to explore the city! Tickets are required just to reserve your spot because some locations fill up quickly.

Adults Night Out at Lincoln Park Zoo

Lincoln Park Zoo hosts an adults-only event called OkSOBERfest on September 17th. You’ll have access to unique animal chats, games, free rides on the carousel, a live DJ, NA drinks, and food options throughout the zoo all evening.

I hope this helps with date night ideas in Chicago this fall! I’ve got more fun activity recommendations in my Fall Bucket List Roundup here!


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