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Cheap, But Fun, Date Night Ideas in Chicago, IL

The perfect date night doesn’t have to cost a ton of money, at the end of the day it’s really just about spending time together. We’ve put together a list of cheap and FUN date ideas for you and your significant other to take part in, whether it’s sunny and 75 or snow is coming down in Chicago, IL. 

 

christkindl market in chicago
Photo credit: Instagram.com

Shopping around at the seasonal markets 

Winter: Christkindl Market | Summer: Farmers Market 

One of the best things about Chicago is that there’s always something to do, no matter what time of year it is. And one thing Chicago knows how to do is markets. In the summer you can count on there being a farmers market almost any day of the week and you can buy all kinds of produce, baked goods and more. A lot of these farmers markets even run through November, but come winter and the holiday season, you have to check out the infamous Christkindl Market. Whether you’re buying goodies or just going for a stroll and enjoying all of the booths, checking out the markets all around town is a fun and cheap date idea year round. 

 

exterior of music box theater in chicago
Photo credit: Musicboxtheater.com

Go see a movie at Music Box on Southport 

3733 N Southport Ave, Chicago, IL 60613

Music Box is a classic, old school theater that opened up in 1929 in Lakeview. It’s the perfect spot for a movie date night and you can catch all kinds of films from independent, foreign, cult and of course the classics. The vintage vibes in this theater are so cozy and it’ll take you right back to the good old days, and the best part is that the prices are vintage, too! Movies can cost at least $20 at big theaters, at Music Box, you can get tickets for as low as eight bucks. 

 

coffee from colectivo in chicago
Photo credit: Instagram.com/colectivocoffee

Coffee walk in the park 

Two things that this city has tons of? Coffee shops and cute parks! The perfect date doesn’t have to cost a lot of money and we’ve made that pretty clear. Grab a coffee from one of the many adorable coffee shops around town and if it’s nice out, take a stroll through Lincoln Park or Humblot park, sit on a bench and people watch and enjoy each others company.

 

pizza from frasca in chicago
Photo credit: Instagram.com/frascapizzeria

Try a new happy hour spot 

Happy hours are the way to go when you still want to go out for a delicious bite and cocktails but don’t want to drop $100. Luckily, it seems like just about every restaurant in Chicago has a happy hour deal running during the week so be sure to take advantage of them! Plenty of nice steakhouses and seafood restaurants will host a happy hour during the week so you can enjoy the ambiance without the price tag. 

 

Diversey bowling alley in chicago
Photo credit: Drbowl.com

Go bowling at Diversey River Bowl 

2211 W Diversey Ave Chicago, IL 60647

Going bowling with a group of friends is the ideal, fun and cheap activity. Go out for a double or triple date night at Diversey River Bowl for good vibes, music and beer. They are always running deals so be sure to check their website when you book your reservation. This spot is stuck in the early 2000’s and we can’t get enough of it. 

 

sandwich from the fat shallot in chicago
Photo credit: Instagram.com/thefatshallot

Ride bikes on the lakefront trail and have a picnic 

On a nice afternoon in this city, the lakefront is filled with people biking, running, swimming and just enjoying the sunshine. There are Divvy bike stations every few blocks so you can go for a lakefront bike ride until you find a nice little spot to set up camp. You can bring your own food or go somewhere like The Fat Shallot and pick up a few sandwiches to enjoy. 

 

interior of tango Sur in chicago
Photo credit: Tangosurgrill.com

Lots of BYOB restaurants 

Something we love about Chicago is the versatility in the dining/drinking scene. If you want to go to a fancy cocktail bar and spend $24 on a cocktail you can. And you if you want to go out for a good meal and spend no money on alcohol, you can also do that! There’s so many BYOB restaurants all over town so head to your favorite one, maybe split a few appetizers and enjoy sipping on a bottle of wine that you brought from home. 

 

For more recommendations on where to eat and drink in the city, check our our Chicago page, here