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New Yorkers 1st Choice
Guide to Chicago

Cheap fun activities

Finding something to do that keeps you entertained without draining your entire paycheck.

Based on 727 Opinions
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Updated April 2026
01
Reed's Local image 1
Reed's Local image 2
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Dive bar with punk rock charm and nostalgic memorabilia offers a cozy, community-oriented vibe with live local music and pinball machines. The space feels warm despite a rough acoustic setting, attracting a supportive, queer-friendly crowd. Cash-only policy and cheap drinks add to its authentic neighborhood feel.

Events include live music and karaoke that create a lively atmosphere. Hosts focus on making sure everyone has a fun experience in a local, dive bar setting.

Divey, punk rocky bar with a cash-only policy offers cheap beer and shot specials. Prices for beers like Hamm's and handshake combos stay unbeatable.

People are saying

"The karaoke nights here are really lively and fun."

"It's a classic local dive bar with tons of charm."

"I loved the fun activities like karaoke and local music shows."

Good to know

1

Karaoke nights are on Saturdays and Tuesdays, starting at 8pm.

2

Reed's Local is a cash-only bar; an ATM is available on-site.

3

Prices for drinks are welcoming, with beers starting around $4.

02
Timber Lanes Bowling Alley image 1

Old school bowling alley with manual scoring and well-maintained wood lanes creates a nostalgic, vintage atmosphere. The space feels warm and welcoming, attracting a friendly community for relaxed fun. A small bar offers classic drinks like PBR and whiskey, with cash-only payment.

Vintage vibes create a retro bowling alley feel with lanes in great condition. Games cost $3 during off hours, making it a cheap, fun spot for relaxed nights with friends or solo.

Cheap drinks and affordable prices make this bowling alley stand out. The lanes stay in great condition while keeping costs low.

People are saying

"It's a fun, old school bowling alley with a nostalgic atmosphere."

"It's a super chill atmosphere here."

"The staff here for fun activities are awesome and super nice."

Good to know

1

Timber Lanes is cash only, so bring cash for payments.

2

Parking at Timber Lanes can be limited, so arrive early.

3

They host bowling leagues throughout the year.

03
Bernice's Tavern image 1

Small, family-run dive bar with intimate atmosphere and live jazz music. Friendly, laid-back vibe attracts local regulars and colorful community characters. Cash-only setup with limited liquor selection and no food service.

Fun atmosphere makes it a lively spot. Bartenders are kind and engaging, adding to the enjoyable vibe. Wednesdays feature Stingo, which adds to the fun.

Offers very cheap drinks with a no frills local bar vibe.

People are saying

"The live music here makes the atmosphere really great."

"I found the live music and Stingo on Wednesdays to be fun activities."

"I thought it was a spectacular dive bar."

Good to know

1

Bernice's Tavern is cash only; bring cash for drinks and games.

2

Bingo night, called 'Stingo', happens every Wednesday with fun prizes.

3

Live music performances occur regularly, enhancing the bar's lively atmosphere.

04
Big Joe's image 1

Dive bar atmosphere with cash-only policy and turtle races creates a quirky, lively vibe. Crowd enjoys silly fun and local charm in a relaxed setting. Pizza offerings add a casual, tasty touch to the experience.

Endless silly fun keeps the energy high here. Activities offer a steady stream of good laughs and enjoyment.

Cheap pitchers and affordable beer stand out here. Drinks consistently come at a low price.

People are saying

"You've gotta check out the Friday night turtle races at the bar."

"You have to check out the turtle races; they're a blast!"

"I found the drinks here to be cheap."

Good to know

1

Big Joe's is cash only; bring cash for drinks and food.

2

Turtle races happen every Friday night, offering a lively atmosphere.

3

Expect a fun and energetic vibe during the turtle races.

05
Liarโ€™s Club image 1

Classic dive bar with dark, gritty atmosphere and punk rock decor sets a raw, authentic tone. Loud, powerful live music energizes the space, attracting fans of punk and rock scenes. Tight layout offers room to dance without feeling cramped, creating a vibrant, underground vibe.

Fun comes from the rock n roll kiss decor and eclectic vibe. Staff stays friendly and lively, making it a great spot for music fans.

Cheap drinks include beer and shots. Prices stay low throughout the menu.

People are saying

"I found the live music here to be great and the vibes were rad."

"This bar's punk vibe is dark, gritty, and loud."

"It's a fun place with great live music."

Good to know

1

Liarโ€™s Club is cash only, so bring cash for drinks.

2

Street parking is the only option available near Liarโ€™s Club.

3

They host Kiss karaoke around Halloween every year.

06
Brando's Lincoln Park image 1

Bar offers an upscale karaoke setup with an easy queue system and live music on Sundays. Decor combines cozy lounge-like and beautiful aesthetic elements, creating a classy and fun atmosphere. DJs and karaoke hosts maintain a lively vibe with great music and song availability.

Karaoke nights bring a fun atmosphere with a live band adding energy. The overall vibe stays super fun and welcoming for a lively night out.

Drinks come at a cheap price and taste great. Prices stand out as reasonable compared to most spots in the city.

People are saying

"The bartenders here are phenomenal, especially during karaoke."

"Karaoke nights here are so fun, the host really makes it."

"The drinks here are cheap and taste great."

Good to know

1

Karaoke is free, but tips for the DJ are appreciated.

2

Happy hour runs daily from 5 to 7 PM with discounted drinks.

3

There is no cover charge to enter the bar.

07
Rossi's image 1

Dark dive bar with a half-circle bar, limited seating, and country flags hanging from the ceiling creates a true neighborhood vibe. Customers grab beers from refrigerators and bring them to the bar for opening, adding to the casual, self-serve feel. The atmosphere is lively and authentic, with good music and a jukebox enhancing the experience.

Casual, low-key dive bar vibe creates a fun atmosphere. Small size and lighting do not stop it from being a great place to meet people and have fun times.

Drinks come at a cheap price here. The spot feels comfy and welcoming without being a dirty dive bar.

People are saying

"I thought it was the best and most authentic dive bar."

"I had a fun time with a casual, low-key vibe."

"The drinks here are cheap and appropriately priced."

Good to know

1

Rossi's is a cash-only bar that opens at 7am.

2

Rossi's has a full crowd during Riot Fest season.

3

Expect limited seating during peak hours.

08
Blue Chicago image 1
Live music bar

Small, vintage blues bar with an intimate, no-frills setup focused on live music. Atmosphere feels authentic and cozy, with close proximity to local talent performing on a narrow stage at the back. Venue stays lively until late, attracting an enthusiastic crowd and offering cash-only service with room to dance.

A fun, vibrant musical environment fills the small space with a super positive vibe. The crowd stays fun loving but mature, matching the energy of the tight, hardworking band.

Drinks cost between $6 and $10, making them notably cheap. Both beers and other drinks stay within this affordable range.

People are saying

"The live music here is phenomenal and top-notch."

"The live music here is outstanding and kept everyone dancing."

"The drinks here are cheap."

Good to know

1

Blue Chicago is a cash-only bar, so bring cash for drinks.

2

There is a $15 cover charge to enter Blue Chicago.

3

Live performances start at 9pm, with doors opening at 8pm.

09
Cole's Bar image 1

Narrow space combines dive bar vibes with a small concert venue featuring live jam bands and eclectic shows. Walls display local art, and wooden bench booths add to the creative, relaxed atmosphere. Crowd is diverse, lively, and drawn by affordable drinks and authentic counterculture energy.

Loud, divey bars set the tone with fun happenings in the back. The vibe stays cute and lively for a night out.

Cheap drinks stand out here, especially the house lager which is both tasty and affordable compared to typical American beers.

People are saying

"It's a chill, friendly dive bar with pool tables and live music."

"I had a blast at the super funny comedy show."

"It's a really fun place with a great atmosphere."

Good to know

1

There is a $10 minimum for card payments, equivalent to two drinks.

2

Expect a lively atmosphere with frequent live events like comedy and music.

3

Open mic nights happen regularly, showcasing local talent.

10
Christina's Place image 1

Small, cozy bar with pool table and large screens for games creates a laid-back, friendly vibe. Locals gather for karaoke and cheap drinks in a relaxed, neighborhood setting. Atmosphere feels welcoming but can be quiet or awkward for newcomers.

Lots of fun activities happen here, with karaoke being a regular highlight. The spot works well for a shot and a dance.

Cheap drinks stand out here, especially the Guinness which is priced very low. Karaoke adds to the value without raising costs.

People are saying

"Karaoke nights here are a blast and bring everyone together."

"The vibe here is so chill and welcoming."

"The karaoke here is always fun."

Good to know

1

There is a 20-30 minute wait for a chance to sing karaoke.

2

There is a $15 minimum for credit card payments.

3

You can bring your own food to eat while enjoying drinks.

11
Social Junkie image 1
Bar & grill

Bar and grill with indoor and outdoor seating, including a large patio with pool table and bean bag toss. Atmosphere is lively and fun, with loud music and a crowd that enjoys games and sports events. Offers affordable food and drinks with a focus on burgers, wings, and bar snacks.

Fun crowd creates a lively vibe. Bartenders serve drinks fast and keep the energy up. Food and drinks add to the overall fun experience.

Prices stay low with cheap drinks and well-priced items. A cheap beer is easy to find, making it a budget-friendly spot.

People are saying

"The bar's Parma burger and fries were delightful."

"I loved the great beer selection and local taps."

"The service here is always friendly and engaging."

Good to know

1

Trivia night happens every Wednesday at 8pm with a $5 entry fee.

2

Open mic events take place every Thursday starting at 7pm.

3

Social Junkie has a large parking lot available for guests.

12
Black Friday Deals Chicago image 1

Shopping feels like a random treasure hunt through bins of very cheap, quality items with prices up to 95% off retail. The space has a fun, casual vibe where customers browse openly, sometimes handling opened or imperfect products. Frequent restocking keeps the selection fresh and unpredictable.

Shopping surprises create a fun experience with great prices that keep things exciting. The store offers a super fun atmosphere for browsing and finding deals.

Many items have very cheap prices with good quality. Shopping feels easy and quick, making it simple to find new items at low costs.

People are saying

"I found the prices to be great and the experience to be fun."

"I found so many cheap items, it was amazing."

Good to know

1

Expect a mad dash for new items on Fridays.

2

Many items are very cheap, with prices up to 95% off retail.

3

Wearing gloves or a mask while shopping is recommended.

13
City Pool Hall & Sports Bar image 1

Pool hall offers 12 well-maintained tables including 9-foot tables in a laid back, friendly atmosphere with fantastic music. Space feels old school Chicago billiards with a no frills environment and a backyard smoking area. It gets crowded but maintains a hometown vibe with a mix of quiet and lively energy.

Playing pool and darts offers a fun way to hang out with friends. Friendly staff add to the lively atmosphere, and several additional games keep the energy up.

Food and beers come at a cheap price here. Drinks have a cheap alcohol taste and are not name brand.

People are saying

"The food here is pretty damn good."

"I had a fun time playing pool and pop-a-shot here."

"The beer here is cheap and cold."

Good to know

1

Pool tables cost $14 per hour for one person, $18 for two, and $21 for three or more.

2

Expect to wait for a table on busy nights, especially league nights.

3

Parking includes metered and free spaces, with about 20 spots available in front.

14
K POP & MORE image 1

Cozy store filled with wide variety of K-pop merchandise and affordable prices. Walls display many posters, and a photo booth adds a fun, interactive element. The space feels welcoming and comfortable, with seating available for companions.

Photo booth and decorations in the back create a fun spot for pictures. Arcade games and hosted events add lively activities. Staff interactions bring a friendly vibe.

Prices stay consistently cheap for albums compared to other K-pop stores. Some products show a cheap appearance, which may affect perceptions of value.

People are saying

"I found the albums and merchandise here to be really affordable."

"I thought the prices were really cheap compared to other stores."

"The photo booth and decorations are a fun addition."

Good to know

1

K POP & MORE has the most affordable prices for K-pop merchandise in Chicago.

2

The store offers a wide variety of albums from both girl and boy groups.

3

They host free events regularly, which are fun and engaging.

15
Waveland Bowl image 1
Bowling alley

Bowling alley offers nostalgic atmosphere with loud music and flashy videos above lanes. Crowds include families and birthday parties, creating a fun, lively vibe. Amenities include arcade games, pool tables, and mood lighting for late sessions.

Cosmic bowling nights create a crazy fun vibe with lively music and a super fun atmosphere. The venue suits family outings, birthday parties, or casual hangouts, offering a convenient spot to relax and enjoy.

Bowling lanes and drinks come at cheap prices here. The spot offers affordable fun for hanging out with friends.

People are saying

"It's a super fun place to hang out with friends."

"The food here is surprisingly great and reasonably priced."

"I found the bowling to be cheap and fun."

Good to know

1

Cosmic nights are popular, but some lanes are reserved for league play.

2

Bowling and billiards have great deals from Monday to Wednesday before 4 PM.

3

Bowling costs $60 an hour after 6 PM.

16
Friar Tuck image 1

Cozy dive bar with a neighborhood-style vibe and historic charm featuring 1950s cash registers. Atmosphere stays chill and welcoming, attracting an easygoing crowd that fills up by late evening. Offers free popcorn and a jukebox, creating a casual spot for hanging out or bar crawls.

Fun theme nights like trivia and karaoke create a lively atmosphere. Sunday night bingo and Wednesday trivia add variety to the fun activities available.

Drinks come at cheap prices with daily specials and monthly beer deals. Bar staff stay friendly throughout.

People are saying

"The bartenders here are amazing and remember your name."

"I found the drinks here to be cheap."

"I found the Wednesday night trivia to be fun."

Good to know

1

Karaoke night is every Tuesday, attracting a younger crowd.

2

Trivia happens on Wednesdays at 8pm with a lively host.

3

Seating fills up quickly on weekends, so arrive early.

17
Superdawg Drive-In image 1
Hot dog stand

Drive-in hot dog stand with car hop service and classic 1950s style creates a nostalgic atmosphere. Eating in cars or at outdoor seating offers a fun family vibe with an authentic old-school Chicago feel. Iconic giant hot dog on the roof marks the well-maintained location.

Carhop service adds a fun throwback vibe. The drive-in offers a whimsical atmosphere and a retro experience that feels entertaining and nostalgic.

Affordable crewneck sweatshirts cost around $24 and hold up well after many washes. Other prices feel less cheap, especially compared to a $5 hot dog and fries deal in the city.

People are saying

"I thought the hot dogs and cheeseburgers were great."

"It's a fun retro drive-in with unmatched carhop service."

"I found the prices here to be cheap."

Good to know

1

Superdawg Drive-In is a drive-in restaurant where you eat in your car.

2

Parking at Superdawg Drive-In can be challenging.

3

The bathroom is very clean and well-maintained.

18
Voodoo Doughnut image 1
Donut shop

Donut shop showcases vibrant pink decor and a whimsical donut display that creates a playful, energetic atmosphere. Loud music and occasional noisy groups contribute to a chaotic vibe. The space offers custom donut creations and a photo booth, blending fun with unique treats.

The place offers a fun experience with its New Orleans and Voodoo themes adding unique flair. The selection of donuts keeps the visit lively and enjoyable.

Prices range from $1 to $5 per donut, making them very affordable. The jelly filling tastes bland but keeps costs low.

People are saying

"The vegan donuts here are amazing, with many creative options."

"The donuts were cheap, costing between $1 and $5 each."

"The donuts were excellent and tasted great!"

Good to know

1

Parking can be hard to find, especially during peak hours on weekends.

2

Voodoo Doughnut offers a wide variety of unique flavors.

3

Vegan options are available and are clearly marked on the menu.

19
EL RINCON DE FABIO LLC image 1
Venezuelan restaurant

Small space filled with beautiful Venezuelan decor and a cozy, family-friendly atmosphere. Latin music plays softly, creating an awesome vibe that feels welcoming and pleasant. Outdoor patio offers a nice option for seating in good weather.

Fun atmosphere shines with lively music and an engaging environment. Authentic dishes add to the overall delicious and enjoyable experience.

Food comes in huge portions and costs very little. Specials offer solid, cheap bites but some dishes use cheap ingredients and have small portions.

People are saying

"I found the pabellรณn arepa to be delicious."

"The atmosphere here is so fun and the food is delicious."

"The food here is cheap, tasty, and has huge portions."

Good to know

1

Free drinks are offered after 5pm every day.

2

Enjoy free margaritas daily after 2:00 PM.

3

Free wine is available on Fridays.

20
Snickers Bar & Grill image 1

Dive bar with a wraparound bar, seven TVs, and an internet jukebox creates a lively, classic pub vibe. Front room buzzes with sports energy and regulars chatting, while back booths offer a cozier, relaxed setting. Atmosphere blends nostalgic charm with unpretentious laughter and casual dining.

Late night visits offer quick and fun experiences. The bar keeps a lively and engaging atmosphere throughout.

Offers cheap drinks like $3 mystery shots and cheap beers with generous pours. Food prices stay low, making it a solid spot for a quick, affordable meal in an expensive area.

People are saying

"This bar is a gritty, local hangout with a nostalgic vibe."

"It's a fun bar with a lively atmosphere and a good mix of people."

"I found the food and drinks to be cheap."

Good to know

1

The drink prices at Snickers Bar & Grill are reasonable for downtown Chicago.

2

They accept both credit card and cash payments.

3

The parking lot is small and often full, making parking challenging.

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