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Fun, affordable date spots in Chicago

Popular Chicago influencer @bestdatenight shares their favorite fun and affordable date spots in the Windy City.

January 25, 2023
 min read
Last updated:
Jan 15
A man and a woman holding hands at a restaurant.

We caught up with popular Chicago influencer @bestdatefood to ask them some questions about their favourite Chicago date spots.

1. Where is a fun brunch spot that is still a good deal?

Choice: Taquizo.

Brunch dates are the best dates, right?! While brunching in Chicago has become incredibly popular, it can still be difficult to find a fun place that also has good prices! Look no further than Taquizo in Wicker Park! They have good food at affordable prices, but the star of the show is their amazing bottomless mimosas deal! While many places in Chicago charge around $30-$35 per person, Taquizo comes in at a wildly low $12 per person! Combine that with a DJ and fun atmosphere and you just found your new brunch spot to check out!

2. Where is your go-to restaurant for a first date and why?

Choice: Centennial Crafted Beer & Eatery

When we think of a good first-date restaurant, we want somewhere that will have a classy atmosphere, high-quality food and plenty of options to choose from that won’t break the bank! Centennial in River North has just that. It sits in a historic, yet renovated building with exposed brick and beautiful woodwork throughout. They have 56 beer taps with 36 rotating craft beers, an extensive cocktail list and wine as well! Pair this with their equally impressive chef-driven menu (get the Mac + Cheese), and we have a great spot on our hands! Last but not least, they have a weekly happy hour with $5 pints, $7 wine and a couple half-price apps! 

3. Where would you take someone for a special romantic dinner, like an anniversary, that’s still great value for money?

Choice: Geja’s Café

Lincoln Park is where you will find Chicago’s most romantic restaurant: Geja’s Café. This is Chicago’s premier fondue restaurant, and we all know that fondue makes for a great date night! The candle-lit dining room, wine-cellar vibes and live music create an atmosphere perfect for any special evening. You can even work with the restaurant to have custom flower arrangements added to your table! For the first hour they are open each day, they have 50% off cocktails and 25% off all wine bottles! Additionally, every Wednesday you can get $10 off all their wine flights! 

4. Where’s the best spot for a summer date?

Choice: Miku Sushi

Summer in Chicago means that it is patio season! Miku Sushi in Lincoln Square has a nice front patio and an amazing happy hour that is even available on the weekend! Every day from 4-6pm, you can get $6 Martinis from and half off sushi! It’s simply one of the best happy hour deals in all of Chicago! There are 33 Classic and Traditional Makis that qualify for half off! 

5. What about a winter date?

Choice: Trivoli Tavern

If you are looking to escape the Chicago winter, there is no better place to feel warm and cozy than Trivoli Tavern in West Loop! You have to search a little to find this old-school, American tavern hiding down a cobblestone courtyard, but it’s absolutely worth it! Immediately upon entering, you feel like you’ve been transported into the past. It’s incredible, just like the happy hour prices with $6 Martinis, draft beer and wine, plus five different food deals as well! Don’t miss half-off wine bottle Wednesdays as well! 

6. Where would you take a date who is brand new to the city?

Choice: Chicago Riverwalk

If you are new to Chicago, you will learn quickly that Chicago comes alive during the warm weather months! In our opinion, there is no better place to experience it and all the city has to offer than on the Chicago Riverwalk! It’s a 1.25-mile long, beautifully constructed path that runs adjacent to the Chicago River! It’s free and open to the public from 6am – 11pm. Bring your date there to get some steps, have a meal, grab drinks, people watch or just relax and talk!

7. What is one of your favorite happy hour spots?

Choice: Osteria Via Stato

Happy Hour is the most important meal of the day, right?! In Chicago, it most certainly is! A ton of places offer great deals that will allow you to save money when dining out. One of our personal favorites is Osteria Via Stato in River North. They have 50% off all six of their pizzas and 50% off select wines by the glass! You can get an entire cheese pizza for $6.48, charred pepperoni for $7.98 and a glass of wine for $6! You can get this deal every single day during the first hour that they are open. Sunday-Thursday it’s from 5pm-6pm and Friday-Saturday it’s 4:30pm-5:30pm. Add it to your happy hour list!



So there you have it, seven incredible Chicago date spots that won't break the bank. If you're looking for more great things to do (and eat!) around Chicago check out our full Chicago City Guide.

*Prices fluctuate based on season and day of the week.

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Best Date Food is Chicago’s trusted source for what to do and where to go, highlighting local restaurants, events, news and more! Their videos have garnered millions of views and hundreds of thousands of followers across social platforms. In 2021, Best Date Food launched Best Date Foodies, a community where members save money when dining out in Chicago by gaining access to amazing restaurants discounts, which rotate on a monthly basis.