Chicago
Group
Rides

Mondays; 6:00 pm

Dunkin Donuts at Lincoln and California

20-25 mph; 30-35 miles

Link to route

Link to ride website

emphasis on smooth riding techniques, paceline etiquette, practice sprints, and building confidence on the open road

Updated on 6/13/2023

Mondays; 6:00 pm

Specialized Chicago Lincoln Park

Distance may change, so please check the Strava event to see what's on the menu.

Link to ride website

Join us at Specialized Lincoln Park for our weekly Monday night ride! Distance may change, so please check Strava or our IG @unofficial.race.team to see what's on the menu.

Updated on 5/7/2025

Mondays, 6:15 pm

Prospect Park

16 miles with cruising speeds capped at 18mph and 14mph for the two groups

Link to ride website

Monday Social Rides depart summer evenings at 6:15 pm in front of the Park Ridge library, 20 S Prospect Ave. A 1-hour loop into Glenview. Two speed options. Newcomer? Start here! Rides often end at Beer on the Wall or Harp & Fiddle (both on Main St.) for those who wish to grab dinner or a drink. Rides run June 3 to Sept 9 (first Monday after Memorial Day to the first one after Labor Day). For September rides, bring front and rear lights.

Updated on 12/29/2025

Monday, 5:30am

LA Fitness Parking Lot (3435 S. King Dr., Chicago, IL)

13-14 MPH, 20 miles

Link to ride website

Check the website for more information.

Updated on 5/13/2025

Monday, 6:15am

Lansing Woods Parking Lot (186th St. & Oakley Ave. Bloom Township, IL)

A 18+ MPH , B 15-16 MPH, A 25 miles, B 23 miles

Link to ride website

Check the website for more information.

Updated on 5/13/2025

Monday, 6:00pm

Pep Boys Parking Lot (21610 Cicero, Matteson, IL)

Multiple Groups 12-17 MPH, 12-25 miles

Link to ride website

Check the website for more information.

Updated on 5/13/2025

Tuesday, 6pm meetup, 6:30 rollout

Pedal & Spoke

casual pace 10-20 miles

From the instagram post announcement: "The whole idea behind this gorup ride is to get out and enjoy ourselves while building a positive and inviting community around cycling!"

Updated on 4/9/2025

Tuesday, Meet at 6pm - roll out as soon as we get the shop closed up

ASU Cycles (Aurora, IL)

Pace depending on who shows up typically anywhere from 16 to 18 mph. Distance 25-40miles, usually around 30/35

No drop, we’ll wait. Begins and ends with daylight savings time change.

Updated on 8/18/2023

Tuesdays, 6:00 pm

Turin Bikes

16-19 mph; 32 miles

Link to ride website

Northern burbs and back

Updated on 4/9/2025

Tuesdays, 5:30 am

Location may vary so check the calendar. Normally will be at Hexe Coffee.

Route is ride leader's choice. Check the calendar for details on pace, route, and distance

Link to ride website

From the SMC website: "summers only . . . we go up to Tower and back . . . some of us need to be to work by 8!"

Updated on 4/9/2025

Tuesdays, 7:30pm (year round!)

Meets in Logan Square. Message on IG for location details

13-20mph rolling speed (14ish full average), 30-50 mi during the summer

Link to ride website

no-drop ride with a mix of pavement, dirt, and gravel.

Updated on 6/13/2023

Tuesdays, 5:30pm

933 Skokie Blvd, Northbrook, IL 60062

Expect a 1.5 hour 36 mile road ride. 2 groups (avg. speed) Group A 26mph+ Group B 21mph+

Link to route

Updated on 4/9/2025

Tuesdays, 5pm

Oak Park

Link to ride website

Tuesdays & Thursdays around 5pm. Drinks/socializing after Thurs night ride

Updated on 4/9/2025

Tuesday, 5:30am

LA Fitness Parking Lot (3435 S. King Dr., Chicago, IL)

13-14 MPH, 20 miles

Link to ride website

Check the website for more information.

Updated on 5/13/2025

Tuesday, 6:15am

Lansing Woods Parking Lot (186th St. & Oakley Ave. Bloom Township, IL)

A 18+ MPH , B 15-16 MPH, A 25 miles, B 23 miles

Link to ride website

Check the website for more information.

Updated on 5/13/2025

Tuesday, 6:00pm

Pep Boys Parking Lot (21610 Cicero, Matteson, IL)

12-15 MPH , 15-25 miles

Link to ride website

Check the website for more information.

Updated on 5/13/2025

Tuesday, 6:00pm

Bartel Grasslands (Central Ave. and Flossmoor RD, Tinley Park, IL)

17+ MPH , 25 miles

Link to ride website

Check the website for more information.

Updated on 5/13/2025

Wednesdays, 6:00 pm

Winnemac Park Parking lot, Winnemac and Damen

16-18 mph; 20 miles

Link to ride website

Please RSVP before showing up!

Updated on 4/9/2025

First Wednesday of each month at 6pm

See Instagram for location

Link to ride website

Supporting BIPOC-owned restaurants and providing a safe space for Femme, Trans, Women, and Non-Binary cyclists of color

Updated on 8/5/2025

Wednesdays, 5:30 pm

Lincoln and California

22-32 mph; 35-40 miles

Link to route

Link to ride website

Great race simulation, advanced riders

Updated on 6/13/2023

Wednesdays, 6pm

Belle Plaine & Damen

20-25 mph, drop ride to Highland Park

Link to route

Updated on 5/1/2024

Every 2nd and 4th Wednesday, 7:15pm

Turin Bicycle

Party pace, ~17 miles

Link to ride website

Party pace, come as you are, any bike, get fresh bagels half way, finish at Turin or Half Acre. New York Bagel & Bialy, 17 miles round trip. Wear helmet bring lights

Updated on

Wednesdays, 5:30pm

8201 N. Caldwell Ave., Morton Grove, IL 60053

Expect a 1.5 hour road ride with a 20+ mph average speed.

We will keep the group together. Look for bikes and red and white jerseys. There will be a mid ride stop at the Highland Park train station.

Updated on 4/9/2025

Wednesday, 5:30am

LA Fitness Parking Lot (3435 S. King Dr., Chicago, IL)

13-14 MPH, 20 miles

Link to ride website

Check the website for more information.

Updated on 5/13/2025

Wednesday, 6:15am

Lansing Woods Parking Lot (186th St. & Oakley Ave. Bloom Township, IL)

18+ MPH , 25 miles

Link to ride website

Check the website for more information.

Updated on 5/13/2025

Wednesday, 5:45pm

7-Eleven Parking Lot (425 Sauk Trail, Park Forest, IL)

18-20 MPH , 24-25 miles

Link to ride website

Check the website for more information.

Updated on 5/13/2025

Wednesdays, 5:30pm

Morettis @ 6415 w Dempster in Morton Grove

20-22 mph average over 35-38 miles (no drop)

We ride from Morettis 6415 w Dempster in Morton Grove (plenty of street parking) at 5:30 and maintain a 20-22 mph average. No drop ride and we'll keep everyone together and stop for mechanicals. Main goal is to keep a nice smooth tempo and stay safe. This is about a 35-38 mile ride up to Fort Sheridan and the route will change from time to time either due to sunset times or based on how the group is feeling. Strava group link to join: https://www.strava.com/clubs/2172397

Updated on 7/4/2026

Wednesdays, 7am

John's place - corner of Roscoe & Hamilton

16-18mph No drop. About 15-20 mi.

Intermediate riders who want a casual, friendly pre-work warm-up ride, but nothing super hardcore and not competitive. No predefined route, and will pick river, lake, etc depending on what the group feels like that day. Anyone who wants to join can email [email protected] or message on WhatsApp via +1-312-888-6360

Updated on 8/7/2024

Various Thursdays, 6:30pm to 7:30pm

BFF Bikes, 2056 North Damen

8-10miles, 12-14mph

Link to ride website

Routes varry, but they always end back at BFF Bikes. Beginner friendly, no previous group experience required.

Updated on 4/9/2025

Thursdays, 5:30 pm starting in April

5440 N. Clark Street in the Walgreens parking lot in Andersonville

Depending who shows; +/-30 miles

Link to route

Link to ride website

No drop, Lights required, Ride ends at Spiteful Brewery 2024 W. Balmoral Ave, Chicago

Updated on 3/3/2024

Every third Thursdays; 6:00 pm

The Bike Lane - 2130 N Milwaukee

chill pace; less than 20 miles

Link to ride website

Check The Bike Lane's Instagram/stories for updates

Updated on 9/14/2022

Last Thursday of every month at 6pm

Reed's Local

6-8 mile ride through the Avondale neighborhood

Link to ride website

Reed's Local Cycling Club! ALL levels welcome. a chill 6-8 mile ride through the Avondale neighborhood 5:30 meetup and mingle 6pm ride out 21+ for inside the bar All ages welcome to ride along

Updated on 7/4/2026

Thursdays, 8pm (see notes)

McCormick Place

typically about 10 miles

Link to ride website

Starting in May, typically Thursday nights at 8pm with some weeks switch to Wednesdays. And some special rides on Saturdays, as well as the Juneteenth ride. Pace at the front is a little fast, but it's open to all paces/skillsets. For more information, visit the website or @streetscalling.bc on Instagram.

Updated on 4/3/2025

Tuesdays, 5pm

Oak Park

Link to ride website

Tuesdays & Thursdays around 5pm. Drinks/socializing after Thurs night ride

Updated on 4/9/2025

Thursday, 5:30am

LA Fitness Parking Lot (3435 S. King Dr., Chicago, IL)

13-14 MPH, 20 miles

Link to ride website

Check the website for more information.

Updated on 5/13/2025

Thursday, 6:15am

Lansing Woods Parking Lot (186th St. & Oakley Ave. Bloom Township, IL)

19-20 MPH , 25 miles

Link to ride website

Check the website for more information.

Updated on 5/13/2025

Thursday, 6:00pm

Bartel Grasslands (Central Ave. and Flossmoor RD, Tinley Park, IL)

18+ MPH , 25-30 miles

Link to ride website

Check the website for more information.

Updated on 5/13/2025

Friday, 6:30am

Check Instagram

average pace 16-18mph

Link to ride website

Meetup location and route change week-to-week. Check Instagram for updates. Please RSVP with the link in our Instagram bio.

Updated on 6/12/2024

Fridays, 6:30am

Fullerton and LFT

16-18 mph, sprint on the south end of LFT

Updated on 4/9/2025

Friday, 5:30am

LA Fitness Parking Lot (3435 S. King Dr., Chicago, IL)

13-14 MPH, 20 miles

Link to ride website

Check the website for more information.

Updated on 5/13/2025

Friday, 6:15am

Lansing Woods Parking Lot (186th St. & Oakley Ave. Bloom Township, IL)

20+ MPH, 25 miles

Link to ride website

Check the website for more information.

Updated on 5/13/2025

Friday, 10:00am

Columbia Woods Parking Lot (8424 Willow Springs RD, Willow Springs, IL)

16 MPH , 25-36 miles

Link to ride website

Check the website for more information.

Updated on 5/13/2025

Friday, 6:00am

Damen and Belle Plaine

17-20 MPH, 27 miles

Updated on 5/31/2025

Friday, 7:00am

Chess Pavilion

18-20mph no drop. 22miles

Starting at Chess Pavilion, ending at Hertiage Coffee and Bikes.

Updated on 5/19/2026

Saturdays, 7:30am meet for a 8:00am roll out

Comrades Cycles, 1908 W Chicago Ave, Chicago, IL 60622

~45 miles, 17mph - 20mph rolling, paceline practice included, no drop

Alternates between North (Highland Park) and South (Wolf Lake). With a coffee stop at the midpoint always (Tala Coffee Roasters in Winnetka and Colibrí in the Southeast Side of Chicago)! Check our social media for the most up-to-date info.

Updated on 7/4/2026

Saturdays 7:30am

Grosse Point Lighthouse

24-34 mph; 50-80 miles

Updated on 4/9/2025

Saturdays, 7:00am starting in April (8am in March)

5440 N. Clark Street in the Walgreens parking lot in Andersonville

Rolling pace of 20-22+ mph; 55+ Miles that Vary each week

Link to ride website

Varies every week join our discord for more info on Saturday rides. Typically stays as one group but may separate into more groups depending on turn out and experience of riders. One stop for midway that can be at a coffee stop, gas station or park depending the route. At end of ride group might end up going to Spiteful for beers.

Updated on 4/24/2024

Saturdays 8am

Belle Plaine & Damen

18-20 mph no drop

Link to route

Updated on 6/13/2023

Saturdays, 8:00am

Hexe Coffee

18-22 mph to Highland Park (with optional extensions)

Link to ride website

From the SMC website: "Great ride for a beginner, we will make sure you get up to Highland Park with us."

Updated on 4/9/2025

usually first Saturday of the month (check social media for details)

Location varies (check social media for details)

depends on who shows up, beginner friendly

Link to ride website

very beginner friendly

Updated on 6/13/2023

Saturdays, 7:00am (summer) Offseason starts at 8am. Goes year round!

Northwest corner of Wicker Park, south of the intersection of North/Damen/Milwaukee

18-22 mph; 47 miles

Link to ride website

Second meeting point at Pratt and Ridge at 7:30. no drop up to HP, drop on the way back. May-Oct start 7:00 AM, Nov-Apr start 8:00 AM. Thorough details are available on the ride page, check it out!

Updated on 4/9/2025

Saturdays, 9am

Addison intersection of the Lake Path

12-15mph, 27 Miles

Link to ride website

Windy City Cycling. A LGBTQ+ cycling group in Chicago.Casual lakefront bike ride to Hyde Park

Updated on 8/16/2023

Saturdays, 7am

Turin Bicycle

16-20mph, no drop, 45 miles

Rolls out at 7am, friendly approachable no drop group ride, pace dependent on group, distance 35-60 miles dependent on group

Updated on

Saturdays, 7:30am

Specialized Fulton Market

18-19mph, 54 miles

Intermediate pace with opportunities along the way and back, to bring up the pace a little bit. After these sections we will give others a chance to catch back on to the group as this is a 'no-drop' ride. Group riding experience is highly recommended.

Updated on 4/9/2025

Saturdays, 10am

Lake Front Trail at Ohio Beach

Casual spin, 1 hour

Link to ride website

The vibe/pace is very chill coffee ride and the club is social centric. Open to anyone.

Updated on 4/9/2025

Saturdays, 9:00am

Dam No. 1 Woods East, 621 W Dundee Rd, Wheeling, IL 60090, 42.136019, -87.900645

Expect a 2.5 hour ROAD Ride. 46 to 50 mile ride with a 19+ mph average speed.

This is a tempo ride and both routes feature a coffee stop and regroup areas, we will do our best to keep the group together. We alternate routes weekly. We do a route to Tala Coffee Roasters and a hilly route that heads west to Barrington.

Updated on 5/28/2024

Saturdays, departure time TBD

Pickwick Theatre

Link to ride website

Group rides are year round, weather permitting, with start times moving based on sunrise. Once we get to the colder months, the best way to be notified is to sign up on our listserv. We run A and B rides year around and C rides between April and October. A/B rides are usually 55 miles with a turnaround option usually 15-20 miles in. C rides are generally 20-35 miles. A/B rides are generally 18-22 mph. B is no drop. C rides are 15-16 mph, no drop.

Updated on 12/29/2024

Saturdays, 7am

Oak Park

Link to ride website

Updated on 4/9/2025

Saturday, 6:00am

La Rabida parking lot (6501 S. Promontory Drive, Chicago, IL)

15-16 MPH , 20-25 miles

Link to ride website

Check the website for more information.

Updated on 5/13/2025

Saturday, 7:30am

Lake Katherine parking lot (7402 Lake Katherine Dr. Palos Heights, IL)

10-12 MPH , 20-30 miles

Link to ride website

Check the website for more information.

Updated on 5/13/2025

Saturday, 8:00am

Jackie Robinson Park (107th St. & S. Sangamon St. Chicago, IL)

10-11 MPH , 10 miles

Link to ride website

Check the website for more information.

Updated on 5/13/2025

Saturday, 8:00am

Bartel Grasslands (Central Ave. and Flossmoor RD, Tinley Park, IL)

17-19 MPH , 62 miles

Link to ride website

Check the website for more information.

Updated on 5/13/2025

Saturday, 8:00am

Palos Heights Public Works (7607 W. College Dr. Palos Heights, IL)

13 MPH , 25-40 miles

Link to ride website

Check the website for more information.

Updated on 5/13/2025

Various Sundays, 8am to 10am

BFF Bikes, 2056 North Damen

12-18miles, 12-14mph pace

Link to ride website

No drop and no previous group ride experience necessary

Updated on 4/9/2025

Various Sundays, 8am to 10:30am

BFF Bikes, 2056 North Damen

16-18 mph, 30-50 miles

Link to ride website

please check the calendar on BFF's site to confirm the ride is being held

Updated on 4/9/2025

Sundays, 7:30am summer (8:30am winter)

5440 N. Clark Street in the Walgreens parking lot in Andersonville

Group A: 25- 30 mph rolling speeds (DROP RIDE with no re-groups); 45 miles

Link to route

Link to ride website

Drop ride, after-ride coffee at Misericordia's Hearts & Flour Bakery and Cafe

Updated on 4/9/2025

Sundays, 7:30am summer (8:30am winter)

5440 N. Clark Street in the Walgreens parking lot in Andersonville

45 miles; Group B will split into B+ and B depending on number of riders that show up. Group B+: 20 - 25mph rolling speeds (Drop Ride). Group B: 17-22mph rolling speeds (No-Drop Ride and Sweeper)

Link to route

Link to ride website

Beginners welcome! No drop, after-ride coffee at Misericordia's Hearts & Flour Bakery and Cafe

Updated on 4/9/2025

Various Sundays, 9:30am

Heritage Coffee

18-20 mph, no drop

Link to ride website

Check social media or Discord to confirm

Updated on 4/9/2025

Sundays, 7:30am (first Sunday of the month) & 7am (all other weeks)

Specialized Fulton Market

See Notes. Variable, check Strava each week for route

Link to ride website

T-Shirt Ride (first Sunday of every month): 30-35 miles, 15mph average, no-drop. Coffee stop at halfway point or end of ride. Wear a t-shirt (or flannel, or crop top, or whatever you want)! This is a social ride and meant to be fun. SMR (all other weeks): 45-60 miles, 19mph average. A/B group splits at the halfway point. Group A: 22mph+ rolling, Group B: 19mph+ rolling. Both are drop groups. No coffee stop. Show up for some spice.

Updated on 5/13/2026

Sundays, 8:00 am

Hexe Coffee

ride leader's choice, details will be on the calendar

Link to ride website

From the SMC website: "This is a ride leader’s choice ride. Normally this ride requires group riding experience. Check the calendar for details. Route varies week to week so always meet at Clybourn and Damen!"

Updated on 4/9/2025

Sundays, 8am

Foster Beach to Fort Sheridan

18-20 mph, 47 Miles

Link to ride website

Windy City Cycling. A LGBTQ+ cycling group in Chicago.

Updated on 8/16/2023

Sundays, 9am

8201 N. Caldwell Ave., Morton Grove, IL 60053

Expect about a 2.5 hour ride. 42 miles with 3 pace groups. Group A is a 25+ mph avg speed - Drop Ride Group B 20+ mph avg speed Group C 17+ mph avg speed

Link to route

There is a stop in Fort Sheridan and an optional coffee stop at Plaza de Lago

Updated on 5/28/2024

Saturdays, departure time TBD

Pickwick Theatre

Link to ride website

Group rides are year round, weather permitting, with start times moving based on sunrise. Once we get to the colder months, the best way to be notified is to sign up on our listserv. We run A and B rides year around and C rides between April and October. A/B rides are usually 55 miles with a turnaround option usually 15-20 miles in. C rides are generally 20-35 miles.

Updated on 12/29/2024

10 rides and tailgates this season, mostly on Tuesdays

Queen’s Landing, across from Buckingham Fountain on the Lakefront Trail (or hop on along the way)

Link to ride website

Chicago Bike Sox is the bike community's summer pastime. They bike to the ballpark and tailgate at the bike racks between gates 2 & 3. Roll from Queen’s Landing, use the ride tracker to hop on along the route, or make your own way and meet up at the racks for the tailgate. The ride is 5 miles at a chill, inclusive pace. Everyone is welcome!

Updated on 5/7/2025

Link to ride website

Check @dykesonbicycles on Instagram for more information about the rides.

Updated on 4/9/2025

Pace varies according to ride and day.

Link to ride website

Chain Reaction Cycling Club (CRCC) a south side based group focused on building better riders. Check Instagram for more information on public rides.

Updated on 4/9/2025

Last Friday of every month, 6pm

Daley Plaza

Link to ride website

Critical Mass is a large group bicycling event, gathering in Chicago the last Friday of every month for decades. Leaves Daley Plaza downtown around 6pm.

Updated on 4/9/2025

First Saturday of the month

Link to ride website

A safe space for women, femme, non-binary and trans Chicagoans to ride bikes together. No-drop social rides every 1st Saturday of the month.

Updated on 4/9/2025

Check Strava for rides that are open to non-members

Rapha Chicago

Link to ride website

Updated on 4/9/2025

Specialized Fulton Market

Link to ride website

Check @indigocyclingchicago on Instagram for details

Updated on 9/9/2024

Link to ride website

The Major Taylor Cycling Club Chicago (MTC3) is dedicated to promoting fitness, fellowship and fun while fostering a sense of community among cyclists, and honoring the legacy of Marshall “Major” Taylor. In addition to the weekly recurring rides, we host additional special rides. Check the website for more information.

Updated on 4/9/2025

First Friday of each month, 6:15 pm

Nichols Park, 55th St. and Kimbark

Route usually 18-22 miles, under 10 mph.

Link to ride website

See Facebook page. April – November. First Friday of the month, departs from Nichols Park, 55th St. and Kimbark 6:15 pm. Route usually 18-22 miles, under 10 mph.

Updated on 1/10/2025