Chicago Travel & City Adventures

10 Unique Fall Date Nights in Chicago

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.

So here’s my Fall 2022 list of ideas for date nights in Chicago!

Food & Drinks

Celebrate Oktoberfest with a 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! 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!

Lincoln Park Wine Fest

The next one is for my wine lovers! Jonquil Park gets transformed into an open-air market featuring wine and food pavilions for the 6th annual Lincoln Park Wine Festival, happening Oct. 7-9. General admission tickets are $40 presale ($55 at the door if available) and include 12 tastings, a commemorative wine glass, and tasting access. Lines do get long, so I would go early! This would be such a fun date night out and then end it with dinner at Galit or La Crosta for wood-fired pizza (it’s so good!).

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 23 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. Tickets are $40-$95 plus fees.

Bloody Mary fest is a unique fall date night idea in Chicago!
Bloody Mary fest is a unique fall date night idea in Chicago!

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!


See a Halloween Movie at Music Box

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 this year’s theme is Scared Stupid! Whether it’s Gremlins 2, Jennifer’s Body, or Nosferatu, these scary movies are great to experience during the spooky fall season!


Earlier this year I went to WhirleyBall 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 with your special someone!

Whirlyball is so much fun! It is great for teenagers and adults! Love this for a date night idea in Chicago.

The Magic Parlour at Palmer House Hotel

This is definitely more of a splurge activity, but so unique! Take your partner to a one-of-a-kind experience at The Magic Parlour. It’s a bit of magic, some drinks, mind reading, and just a full show! It’s definitely a bit of a splurge, but I think it is totally worth it!


Explore Pilsen
Check out the National Mexican art Museum in Pilsen for a fall date night or even day idea.
Dia de Los Muertos at the National Musuem of Mexican Art

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 Howl-o-ween on Thursday, October 27. Early bird tickets are $15. You’ll have access to unique animal chats, games, free rides on the carousel, a live DJ, and multiple bars and food options throughout the zoo all evening. Take in the beauty of the gardens while you wander paths with refreshment in hand—and savor fall in the best way possible.

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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