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The Zig Zag bridge in the Chicago Botanic Garden's Japanese Garden.
The Zig Zag bridge in the Chicago Botanic Garden's Japanese Garden. | © Kaosfere / WikiCommons
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11 Free and Cheap Date Ideas to Try in Chicago, IL

Picture of Sarah Ashley
Updated: 6 April 2018
Let’s face it: as much as we all might like to be millionaires, we just aren’t. In any case, being on a budget is the smart, responsible thing to do! In cities like Chicago, where the cost of living can be pretty high, finding new activities for date night can feel draining – especially on the wallet. It’s a good thing there are tons of excellent options for couples looking to save up for a trip to Mexico (to avoid the winter) or a new puppy (to avoid being without a puppy). Here are 11 free and cheap date ideas for Windy City couples in every tax bracket.

Quenchers Saloon

Bar, American, Vegetarian, Vegan, $$$
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The outdoor patio at Quenchers Saloon.
The outdoor patio at Quenchers Saloon. | © Joram Zbichorski / Quenchers
On the corner of Fullerton and Western in Chicago’s Logan Square neighborhood is a homey bar serving beer from all over the world. Dubbed “Chicago’s Original Beer Bar,” Quenchers Saloon boasts a beer list hundreds of labels long with options from India, New Zealand, Estonia and Japan, to name just a few. The venue also hosts free improv entertainment on Mondays and concerts for as little as $6 throughout the week. With new happy hour specials daily from 4 p.m. – 8 p.m. (and $2 beers on Mondays) and free popcorn out of an enormous popcorn machine, this friendly dive is a must-visit for couples looking for a night out on a budget.
More Info
Mon - Fri:
12:00 pm - 2:00 am
Sat:
11:00 am - 3:00 am
Sun:
11:00 am - 2:00 am

Meal service:

Dinner, Lunch, Late Night

Atmosphere:

Casual

Chicago Botanic Garden

Botanical Garden
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The Zig Zag bridge in the Chicago Botanic Garden's Japanese Garden.
The Zig Zag bridge in the Chicago Botanic Garden's Japanese Garden. | © Kaosfere / WikiCommons
The Chicago Botanic Garden is a tropical, exotic retreat just outside Chicago in the city of Glencoe. Accessible by car, bicycle or a $3.25 Metra train ticket, the park boasts 27 unique gardens and four specific nature areas across 385 acres. Admission is free to the gardens, which is a huge draw for Chicagoans. Other reasons to visit? The Botanic Garden’s enormous bonsai tree collection and its annual orchid show exhibition. This is a perfect date option or day-trip for couples seeking a little adventure and a lot of romance.
More Info
Sun - Sat:
8:00 am - 7:00 pm

Accessibility & Audience:

Accessible (Wheelchair), Kid Friendly, Family Friendly

Services & Activities:

Guided Tours, Free, Fitness classes

Atmosphere:

Outdoors, Indoors, Scenic

Ghareeb Nawaz

Restaurant, Indian, Pakistani, Vegetarian, $$$
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Choose between 22 different types of Paratha at Ghareeb Nawaz.
Choose between 22 different types of Paratha at Ghareeb Nawaz. | © Ravishankardubey / WikiCommons
Couples that enjoy delicious meals for hot prices must venture to Ghareeb Nawaz on Devon Avenue. The restaurant serves mouth-watering Indian and Pakistani cuisine such as chicken tikka tandoori and lamb biryani – and those dishes are just the tip of the iceberg. This place also starts serving early in the morning and doesn’t stop until late at night, so any time of day that suits you, suits them. Plus, nothing on the entire menu costs more than $7 and the portions are big enough to share. The only problem with this place is the long line – so get there early!
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Guthrie's Tavern

Bar, American, $$$
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With over 70 beer, wine and cider options at Guthrie's Tavern, it's impossible to go wrong.
With over 70 beer, wine and cider options at Guthrie's Tavern, it's impossible to go wrong. | © Quinn Dombrowski / Flickr
Hitting up a hip bar for craft beer or cocktails is an obvious date night option. Not so obvious? Hitting up bars with craft beer, cocktails and board games for entertainment. Guthrie’s Tavern in Lakeview is the perfect spot for a couple to get cozy, enjoy a beverage and try to beat each other at Battleship. Or Monopoly. Or Sorry! It’s also a great place for a double date for competitive couples. With more than 10 beers on draft under $7 and a rotating list of specials, it’s hard to beat Guthrie’s for a fun night out. On top of all that, the bar allows you to bring your own food or order delivery.
More Info
Mon - Fri:
5:00 pm - 2:00 am
Sat:
2:00 pm - 3:00 am
Sun:
2:00 pm - 12:00 am

Atmosphere:

Casual, Relaxed, Cosy

Millennium Park Summer Concert Series

Music Venue, Park
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Jay Pritzker Pavilion in Millennium Park just off Chicago's Michigan Avenue.
Jay Pritzker Pavilion in Millennium Park just off Chicago's Michigan Avenue. | © Alanscottwalker / WikiCommons
What’s more romantic than a picnic in the park? Live music at a picnic in the park! Millennium Park’s Summer Music Series offers free concerts several nights a week beginning in June and running through August. Chicagoans can set up blankets, folding chairs, snacks and coolers on the park’s 95,000 sq. ft. lawn before the concerts begin at 6:30 p.m. Sitting outside at dusk under the sparkling city and Jay Pritzker Pavilion as jazz, indie rock or Afrobeat wafts over you is a perfect summertime date night.
More Info
Mon:
6:30 pm - 9:30 pm
Thu:
6:30 pm - 9:30 pm

Accessibility & Audience:

Accessible (Wheelchair), Family Friendly

Services & Activities:

Free

Atmosphere:

Outdoors, Scenic, Architectural Landmark

The Empty Bottle

Concert Hall, Music Venue
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The Empty Bottle as part of Red Bull Sound Select Presents: 30 Days in Chicago, in Chicago, IL, USA on November 15, 2017.
The Empty Bottle as part of Red Bull Sound Select Presents: 30 Days in Chicago, in Chicago, IL, USA on November 15, 2017. | © Koury Angelo / The Empty Bottle
This concert venue is one of the best places to see live music in the city. Luckily, The Empty Bottle offers a free concert series on Monday nights. A wide variety of musicians and bands come through the doors of this Ukrainian Village institution, and free Mondays are no exception. Just like other nights at The Empty Bottle, every Monday features performances by three different groups. In a single night you and your date could catch punk by Absolutely Not, rock by Dumb Vision and indie-pop by No Men. Couples looking for an exciting night of music without having to pay an arm and a leg must check out The Empty Bottle.
More Info
Mon - Wed:
5:00 pm - 2:00 am
Thu - Fri:
3:00 pm - 2:00 am
Sat:
11:00 am - 3:00 am
Sun:
11:00 am - 2:00 am

Accessibility & Audience:

Adults Only

The Paper Machete

Theater, Music Venue
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The Paper Machete is a live magazine hosted by The Green Mill.
The Paper Machete is a live magazine hosted by The Green Mill. | © Gene Jackson / WikiCommons
Every Saturday afternoon at The Green Mill, a jazz club on Chicago’s north side, comedians and musicians perform a comedy variety show. The Paper Machete is marketed as a “live magazine,” because all performances pertain to current events from the previous week or so. For the right price of $0, audience members are treated to comedic essays, character monologues and music by some of Chicago’s (and the country’s) most talented goofballs and writers. Now, with an additional performance on Wednesday evenings, patrons can expect to hear new material, experimental performances and something hysterical twice a week.
More Info
Wed:
6:30 pm - 8:00 pm
Sat:
3:00 pm - 5:00 pm

Accessibility & Audience:

Adults Only

Services & Activities:

Free

Atmosphere:

Indoors

Old Town Art Fair

Art Gallery, Shop
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The Old Town Art Fair is one of many outdoor art festivals in Chicago.
The Old Town Art Fair is one of many outdoor art festivals in Chicago. | © victorgrigas / WikiCommons
Every summer in the Old Town Triangle Historic District artists from all over the country set up shop for the Old Town Art Fair. As with most street festivals and markets in Chicago, this fair takes place in the summertime and admission is free (though donations are always accepted and appreciated). Since 1950, this fair has graced the Old Town neighborhood and benefited local arts and culture organizations. Complete with a garden walk, live music, local food and drinks, the fair hosts over 250 artists every year. Peruse unique paintings, ceramics, photographs, prints and more with your sweetheart at this “outdoor art museum.”
More Info
Sat:
10:00 am - 7:00 pm
Sun:
10:00 am - 6:00 pm

Accessibility & Audience:

Accessible (Wheelchair), Dog Friendly, Family Friendly, Kid Friendly

Services & Activities:

Free

Atmosphere:

Outdoors, Crowded

Maggie Daley Park

Park
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Slide Crater is a great place for kids inside Maggie Daley Park
Slide Crater is a great place for kids inside Maggie Daley Park | © Monicaacosta34 / WikiCommons
Located just outside Millennium Park in downtown Chicago, Maggie Daley Park features tons of activities for people of all ages. The site offers a playground for kids, a climbing wall, picnic tables, a skating ring and more. Dedicated to Maggie Daley, the city’s former first lady and founder of several several arts programs for teens, the park is a reminder of her generosity and devotion to educating young people. Admission is free, but we highly recommend paying the $11 fee to play a round of mini golf. A course designed with Chicago architecture in mind, players have to navigate obstacles including a 6-ft.-tall Willis Tower. With the city skyline in the background, this is a terrific downtown date option.
More Info
Mon - Sun:
6:00 am - 11:00 pm

Accessibility & Audience:

Accessible (Wheelchair), Kid Friendly, Family Friendly

Services & Activities:

Free, No Smoking

Atmosphere:

Outdoors

The Annoyance Theatre & Bar

Theater
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The Annoyance Theater & Bar in Chicago's Belmont Theater District.
The Annoyance Theater & Bar in Chicago's Belmont Theater District. | © The Annoyance Theater & Bar
Located in the heart of Lakeview, just a few doors down from the Belmont L train stop, this quirky theater is the best place to find cutting-edge comedy in Chicago. The Annoyance Theater & Bar serves up original comedic musicals, plays, improv shows and stand-up sets seven nights a week. The venue is also known for pushing the envelope when it comes to subject matter; its original musical “Co-Ed Prison Sluts” is the longest running musical in the city’s history. Their Friday night midnight sketch show, “The Holy Fuck Comedy Hour,” is free and most shows during the week are less than $10 per ticket.
More Info
Sun - Sat:
6:00 pm - 2:00 am

Accessibility & Audience:

Accessible (Wheelchair), Adults Only

Museum of Contemporary Art

Art Museum
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A stunning stairwell at the Museum of Contemporary Art in Chicago.
A stunning stairwell at the Museum of Contemporary Art in Chicago. | © Kris / Flickr
Chicago is the perfect city for lovers, art and lovers of art. The Museum of Contemporary Art houses multiple must-see exhibitions, from the works of Andy Warhol to its unique in-house artist residency program. With innovative galleries, performances and educational programs, you are guaranteed to leave inspired. On Tuesdays, admission is free for Chicago residents. This is just one of many free museum days offered around Chicago; The Chicago History Museum offers free admission to everyone, no matter residency, on Tuesdays from 12:30 p.m. – 9 p.m. Even better? The National Museum of Mexican Art is free every day to every visitor.
More Info
Tue:
10:00 am - 9:00 pm
Wed - Thu:
10:00 am - 5:00 pm
Thu:
10:00 am - 9:00 pm
Sat - Sun:
10:00 am - 5:00 pm

Accessibility & Audience:

Accessible (Wheelchair), Accessible (Deaf), Accessible (Blind)

Services & Activities:

Guided Tours

Atmosphere:

Indoors, Instagrammable