Things to do with friends in Chicago, IL

What are fun things to do with friends in Chicago?

We checked 56 real places in Chicago, IL from OpenStreetMap, including 8 places to eat, 8 bars and nightlife spots (21+) and 8 sights. Squad Plan's three day plans below draw on these places, and your group can vote on the one you like best.

Last updated 2026-10-14

We found 8 places to eat, 8 bars and nightlife spots (21+), 8 sights, 8 parks and outdoor spots, 8 game spots, 8 sports venues and 8 places to shop in Chicago, from OpenStreetMap map data.

Three ready-made day plans

Costs are rough estimates per person in US dollars. Check hours and prices before you go.

Plan A

Historic Pullman Foundation Exhibit Hall to Jovial Club

Slow pace, good food, plenty of time to talk. Group of 4 for friends hangout.

Estimated total per person: $69–210

10:00Visit Historic Pullman Foundation Exhibit Hall
Chicago, IL 60628
Free to $25 (estimate)
11:00Explore Luella Park
10021, Chicago, IL 60617
Free
12:30Lunch at Casa Del Sol
8918 South Commercial Avenue, Chicago, IL 60617
$12–20 (estimate)
14:00Play at Skyway Bowl
9915 South Torrence Avenue, Chicago, IL 60617
$15–30 (estimate)
15:00Get active at Bradley Park Fieldhouse
9729 South Yates Avenue, Chicago, IL 60617
$10–25 (estimate)
16:00Browse Boxville
330 East 51st Street, Chicago, IL 60615
Free to $40 (estimate)
18:30Dinner at Taquería Picazo
9710 South Commercial Avenue, Chicago, IL 60617
$20–40 (estimate)
20:30Drinks at Jovial Club
9615 South Commercial Avenue, Chicago, IL 60617
$12–30 (estimate)

Plan B

A. Philip Randolph Pullman Porter Museum to O’Hara’s Tavern

A fuller day of sights and new places. Group of 4 for friends hangout.

Estimated total per person: $69–210

10:00Visit A. Philip Randolph Pullman Porter Museum
10406 South Maryland Avenue, Chicago, IL 60628
Free to $25 (estimate)
11:00Explore Pine Park
9507, Chicago, IL 60617
Free
12:30Lunch at Cocula Restraunt
8847 South Commercial Avenue, Chicago, IL 60617
$12–20 (estimate)
14:00Play at Lawn Lanes
6750 South Pulaski Road, Chicago, IL 60629
$15–30 (estimate)
15:00Get active at Dr. Conrad Worrill Track and Field Center
10201 South Cottage Grove Avenue, Chicago, IL 60628
$10–25 (estimate)
16:00Browse 61st Street Farmers Market
East 61st Street, Chicago, IL 60637
Free to $40 (estimate)
18:30Dinner at Mariscos El Malecon
9706 South Commercial Avenue, Chicago, IL 60617
$20–40 (estimate)
20:30Drinks at O’Hara’s Tavern
3541 East 106th Street, Chicago, IL 60617
$12–30 (estimate)

Plan C

Ford Calumet Environmental Center (FCEC) to Crow Bar Inc

High energy from start to finish. Group of 4 for friends hangout.

Estimated total per person: $69–210

10:00Visit Ford Calumet Environmental Center (FCEC)
11555 South Stony Island Avenue, Chicago, IL 60617
Free to $25 (estimate)
11:00Explore Dinah Washington Park
8213, Chicago, IL 60617
Free
12:30Lunch at Gusi's Pizza
10606 South Torrence Avenue, Chicago, IL 60617
$12–20 (estimate)
14:00Play at Dr. Martin Luther King, Jr. Family Entertainment Center
7600 South Racine Avenue, Chicago, IL 60620
$15–30 (estimate)
15:00Get active at Tuley Park Fieldhouse
501 East 90th Place, Chicago, IL 60619
$10–25 (estimate)
16:00Browse The Maxwell
1100 South Canal Street, Chicago, IL 60607
Free to $40 (estimate)
18:30Dinner at A Town Wings
9119 South Commercial Avenue, Chicago, IL 60617
$20–40 (estimate)
20:30Drinks at Crow Bar Inc
4001 East 106th Street, Chicago, IL 60617
$12–30 (estimate)

Family friendly things to do in Chicago

Real places in Chicago for a day out with kids.

Visit Bronzeville Children's Museum
A good first stop for a family day. Check the hours before you go.
Free to $25 (estimate)9301 South Stony Island Avenue, Chicago, IL 60617
Visit Clara D. Schafer Park
Free to visit, with room to run around. Bring snacks and water.
Free8900, Chicago, IL 60617
Eat at New Hot Wok
A sit-down meal for the whole family. Call ahead for a big group.
$12–20 (estimate)10611 South Ewing Avenue, Chicago, IL 60617
Go to Bluebird Lanes
Mini golf, bowling and arcades are easy for kids. Check the hours before you go.
$15–30 (estimate)3900 West Columbus Avenue, Chicago, IL 60652
Go to AMC Ford City 14
Movies, games or bowling for a rainy or hot afternoon. Check showtimes and hours first.
$15–30 (estimate)7601 South Cicero Avenue, Chicago, IL 60652
Snack stop at Dulce's Café
A quick stop for drinks and a snack between activities.
$8–18 (estimate)2957 East 88th Street, Chicago, IL 60617

Make a family plan for Chicago

Date night ideas in Chicago

Real places in Chicago for two people, with a rough cost per person.

Coffee at Dulce's Café
Short, cheap, and easy to make longer if it goes well.
$8–18 (estimate)2957 East 88th Street, Chicago, IL 60617
Walk through Park No. 588
Free, and easy to talk while you walk side by side.
Free10440, Chicago, IL 60628
Look around Vanderpoel Art Museum
Something to look at together, so there is always something to talk about.
Free to $25 (estimate)9625 South Longwood Drive, Chicago, IL 60643
Play a round at Skyway Bowl
Something to do together, so you are not just making small talk across a table.
$15–30 (estimate)9915 South Torrence Avenue, Chicago, IL 60617
Dinner at Casa Del Sol
Pick a table where you can talk, and share a few dishes if you both like that.
$20–40 (estimate)8918 South Commercial Avenue, Chicago, IL 60617
Drinks at Family Den (21+)
One drink, then decide together if the night keeps going.
$12–30 (estimate)8942 South Stony Island Avenue, Chicago, IL 60617

Make a date plan for Chicago

Things to do with a large group in Chicago

Real places in Chicago for a group of 10 or more people.

Bowling at Skyway Bowl
Teams take turns, so everyone stays in the game. Book lanes ahead for a big group.
$15–30 (estimate)9915 South Torrence Avenue, Chicago, IL 60617
Play at Seven Ten Social
Ask about group rates and book ahead before you go.
$15–30 (estimate)1055 East 55th Street, Chicago, IL 60637
Park time at Dougherty Park
Bring a ball, a frisbee or lawn games. Free, and easy to split into smaller groups.
Free9336, Chicago, IL 60617
Dinner at Casa Del Sol
Book ahead for a big table, and ask if they can seat your group together.
$20–40 (estimate)8918 South Commercial Avenue, Chicago, IL 60617
Drinks at Riverfront Saloon Inc (21+)
Only for groups where everyone is 21+. Ask about a reserved table for a big party.
$12–30 (estimate)3301 East 106th Street, Chicago, IL 60617

Make a group plan for Chicago

Weekend in Chicago with friends

A two-day plan of real places in Chicago, from Saturday morning to Sunday afternoon.

Saturday morning: Ridge Historical Society
Start the day with a museum, gallery or other sight. Check opening days before you go.
Free to $25 (estimate)10621 South Seeley Avenue, Chicago, IL 60643
Saturday lunch: Casa Del Sol
Sit down together for lunch. Book ahead if the group is big.
$12–20 (estimate)8918 South Commercial Avenue, Chicago, IL 60617
Saturday afternoon: South Chicago People's Park
Free, and easy to split up and meet again. Good for a walk between stops.
FreeSouth Chicago, Chicago, Illinois
Saturday night: Loncar Chico (21+)
A drink or two to end the day. Everyone needs to be 21 or older.
$12–30 (estimate)3201 East 92nd Street, Chicago, IL 60617
Sunday morning: coffee at Dulce's Café
A slow start for the last day. Quick, cheap, and easy to fit a group in.
$8–18 (estimate)2957 East 88th Street, Chicago, IL 60617
Sunday afternoon: Black Cinema House
Bowling, an arcade or a movie. Something to do together before heading home.
$15–30 (estimate)7200 South Kimbark Avenue, Chicago, IL 60619

Make a weekend plan for Chicago

Birthday ideas for adults in Chicago

Real places in Chicago for a birthday the whole group will show up for.

Birthday dinner at Casa Del Sol
Book a table for the whole group and let the birthday person order first.
$20–40 (estimate)8918 South Commercial Avenue, Chicago, IL 60617
Play at AMC Roosevelt Collection 16
Something to do together beats only sitting and talking. Book ahead for a big group.
$15–30 (estimate)1011 South Delano Court, Chicago, IL 60605
Drinks at Frank's Tap & Grill (21+)
Finish the night with a round on the group for the birthday person.
$12–30 (estimate)9621 South Commercial Avenue, Chicago, IL 60617
Visit Chinese American Museum of Chicago
A low-key daytime start before dinner, good for a smaller group.
Free to $25 (estimate)238 West 23rd Street, Chicago, IL 60616
Picnic at Eckersall Park
Bring a cake and some snacks. Free, and nobody has to shout over music.
Free2400, Chicago, IL 60617

Make a birthday plan for Chicago

Things to do with friends under 21 in Chicago

Real places in Chicago for a group where some friends are under 21.

Play at Skyway Bowl
Games or fun for the group. Call ahead if the group is big.
$15–30 (estimate)9915 South Torrence Avenue, Chicago, IL 60617
See a movie at AMC Ford City 14
Check showtimes first, and pick a film the whole group can agree on.
$15–30 (estimate)7601 South Cicero Avenue, Chicago, IL 60652
Get active at Gately Stadium
Play, swim or work out together. Some places need a pass or booking, so call first.
$10–25 (estimate)810 East 103rd Street, Chicago, IL 60628
Coffee or a snack at Dulce's Café
A cheap place to sit and hang out. Order something small and stay a while.
$8–18 (estimate)2957 East 88th Street, Chicago, IL 60617
Eat at Casa Del Sol
Order a few dishes to share to keep the bill down. Check the menu online first.
$12–20 (estimate)8918 South Commercial Avenue, Chicago, IL 60617
Hang out at Luella Park
Free to visit. Bring a ball or a frisbee if you want to play.
Free10021, Chicago, IL 60617

Make an under-21 plan for Chicago

Places in Chicago

Places to eat

Casa Del Sol8918 South Commercial Avenue, Chicago, IL 60617
Taquería Picazo9710 South Commercial Avenue, Chicago, IL 60617
Dulce's Café2957 East 88th Street, Chicago, IL 60617
Cocula Restraunt8847 South Commercial Avenue, Chicago, IL 60617
Mariscos El Malecon9706 South Commercial Avenue, Chicago, IL 60617
Gusi's Pizza10606 South Torrence Avenue, Chicago, IL 60617
A Town Wings9119 South Commercial Avenue, Chicago, IL 60617
New Hot Wok10611 South Ewing Avenue, Chicago, IL 60617

Bars and nightlife (21+)

Jovial Club9615 South Commercial Avenue, Chicago, IL 60617
Family Den8942 South Stony Island Avenue, Chicago, IL 60617
O’Hara’s Tavern3541 East 106th Street, Chicago, IL 60617
Riverfront Saloon Inc3301 East 106th Street, Chicago, IL 60617
Loncar Chico3201 East 92nd Street, Chicago, IL 60617
Crow Bar Inc4001 East 106th Street, Chicago, IL 60617
Frank's Tap & Grill9621 South Commercial Avenue, Chicago, IL 60617
Bar 10610649 South Pulaski Road, Chicago, IL 60655

Sights

Historic Pullman Foundation Exhibit HallChicago, IL 60628
Bronzeville Children's Museum9301 South Stony Island Avenue, Chicago, IL 60617
A. Philip Randolph Pullman Porter Museum10406 South Maryland Avenue, Chicago, IL 60628
Ridge Historical Society10621 South Seeley Avenue, Chicago, IL 60643
Vanderpoel Art Museum9625 South Longwood Drive, Chicago, IL 60643
Ford Calumet Environmental Center (FCEC)11555 South Stony Island Avenue, Chicago, IL 60617
Chinese American Museum of Chicago238 West 23rd Street, Chicago, IL 60616
Obama Presidential Center Museum6001 South Stony Island Avenue, Chicago, IL 60637

Parks and outdoor spots

Luella Park10021, Chicago, IL 60617
Clara D. Schafer Park8900, Chicago, IL 60617
Pine Park9507, Chicago, IL 60617
Park No. 58810440, Chicago, IL 60628
Dougherty Park9336, Chicago, IL 60617
Dinah Washington Park8213, Chicago, IL 60617
South Chicago People's ParkSouth Chicago, Chicago, Illinois
Eckersall Park2400, Chicago, IL 60617

Game spots

Skyway Bowl9915 South Torrence Avenue, Chicago, IL 60617
Bluebird Lanes3900 West Columbus Avenue, Chicago, IL 60652
Lawn Lanes6750 South Pulaski Road, Chicago, IL 60629
AMC Ford City 147601 South Cicero Avenue, Chicago, IL 60652
Seven Ten Social1055 East 55th Street, Chicago, IL 60637
Dr. Martin Luther King, Jr. Family Entertainment Center7600 South Racine Avenue, Chicago, IL 60620
Black Cinema House7200 South Kimbark Avenue, Chicago, IL 60619
AMC Roosevelt Collection 161011 South Delano Court, Chicago, IL 60605

Sports venues

Bradley Park Fieldhouse9729 South Yates Avenue, Chicago, IL 60617
Gately Stadium810 East 103rd Street, Chicago, IL 60628
Dr. Conrad Worrill Track and Field Center10201 South Cottage Grove Avenue, Chicago, IL 60628
Calumet Park Field House9801 South Avenue G, Chicago, IL 60617
Pullman Community Center10355 South Woodlawn Avenue, Chicago, IL 60628
Tuley Park Fieldhouse501 East 90th Place, Chicago, IL 60619
Scottsdale Park Fieldhouse4558 West 83rd Place, Chicago, IL 60652
Avalon Park Field House1215 East 83rd Street, Chicago, IL 60619

Places to shop

Boxville330 East 51st Street, Chicago, IL 60615
Ford City Mall7501-7601 South Cicero Avenue, Chicago, IL 60652
61st Street Farmers MarketEast 61st Street, Chicago, IL 60637
Super Mall5220 South Pulaski Road, Chicago, IL 60632
Hyde Park Shopping CenterSouth Lake Park Avenue, Chicago, IL 60653
The Maxwell1100 South Canal Street, Chicago, IL 60607
Swap-O-Rama4100 South Ashland Avenue, Chicago, IL 60609
Block 37 Shops108 North State Street, Chicago, IL 60602

How much does a day out with friends cost in Chicago?

Across the three day plans above, a day out with friends in Chicago costs about $69 to $210 per person, from the lowest plan to the highest. Each total adds up the typical price of its stops, so treat it as a rough estimate and check prices before you go.

Frequently asked questions

What can a group do in Chicago for free?

Free places on our list include Luella Park, Clara D. Schafer Park and Pine Park. Plans also leave time to wander around town at no cost.

Where can friends eat in Chicago?

Good places to start are Casa Del Sol, Taquería Picazo and Dulce's Café. The day plans above include food stops from this list.

What is there to see in Chicago?

Sights on our list include Historic Pullman Foundation Exhibit Hall, Bronzeville Children's Museum and A. Philip Randolph Pullman Porter Museum. The full list is in the places section below.

What are good things to do with kids in Chicago?

Try visit Bronzeville Children's Museum, visit Clara D. Schafer Park and eat at New Hot Wok. Every idea here is a real mapped place, with a rough cost per person.

What are good date night ideas in Chicago?

Try coffee at Dulce's Café, walk through Park No. 588 and look around Vanderpoel Art Museum. Start small with coffee or a walk, and save dinner for when it is going well.

What are good things to do with a large group in Chicago?

Try bowling at Skyway Bowl, play at Seven Ten Social and park time at Dougherty Park. Book ahead for a group this size, and send the link so everyone can vote on the plan.

What can friends do on a weekend in Chicago?

Try saturday morning: Ridge Historical Society, saturday lunch: Casa Del Sol and saturday afternoon: South Chicago People's Park. Every stop is a real mapped place, with a rough cost per person.

What are good birthday ideas for adults in Chicago?

Try birthday dinner at Casa Del Sol, play at AMC Roosevelt Collection 16 and drinks at Frank's Tap & Grill (21+). Every idea here is a real mapped place, with a rough cost per person.

What can friends under 21 do together in Chicago?

Try play at Skyway Bowl, see a movie at AMC Ford City 14 and get active at Gately Stadium. Every idea here is a real mapped place. Costs are rough estimates.

Can Squad Plan make a custom plan for Chicago?

Yes. Pick the city, your group and the vibe, and Squad Plan gives you three plans your friends can vote on. It is free for 5 plans a week.

Make a plan for Chicago

Nearby city guides

All city guides