Sailing in Chicago, IL

Three-Hour Sailing Lesson for Two, Four, or Six at Sailboat-X (Up to 54% Off)

Multiple Locations

US Sailing–certified instructors teach students to rig the boat and take the helm on a 33-foot vessel

$250 $132

"Learning The Ropes" or "Learning To Boulder" Classes for One or Two at First Ascent Climbing (Up to 49% Off)

First Ascent Climbing

Multiple Locations

Learn rope skills for climbing up to 6 stories tall, or learn technique for bouldering, a more powerful style of climbing on shorter walls.

$73 $39

$12 for 15 Batting Cage Tokens at Sluggers World Class Sports Bar ($20 Value)

Sluggers World Class Sports Bar


Sports bar’s upstairs game room includes batting cages where guests can practice their swings and crush fastballs

$20 $12

Bike Rentals from Wheel Fun Rentals (Up to 49% Off)

Wheel Fun Rentals

Multiple Locations

Group and solo pedalers mount bicycles, surreys, and other wheeled contraptions to cruise the waterfront and city

$35 $18

Open Roller-Skating with Skate Rentals for Two or Four at The Rink (Up to 52% Off)

The Rink

Far South Chicago

A classic hardwood-maple roller-skating rink eschews inline skates for traditional skates with two rows of wheels

$20 $10

Chicago Bears Tickets

Chicago Bears Tickets


Find tickets for sports, concerts and theatre events on FanXchange’s secondary ticket marketplace and get the best seats for live events.

$47 $47

NIU Huskies vs Toledo Rockets at Guaranteed Rate Field on November 9 at 7 p.m.

Northern Illinois Huskies vs. Toledo Rockets 

Guaranteed Rate Field

The NIU Huskies face their division rivals at a historic Chi-Town Showdown—the first football game ever played on the White Sox’s home turf

$55.40 $38

Chicago Blackhawks Game for Two with Options for Signed Memorabilia (October 30–November 3)

Official Fan Package

United Center

The Blackhawks sink their blades into the season with matches against the Kings, Flames, and Avalanche

$220 $139

5 or 10 Group Martial-Arts Classes at Valko Brazilian Jiu-Jitsu Academy (Up to 62% Off)

Valko Brazilian Jiu-jitsu Academy

Near North Side

Group martial-arts classes available in varying belt levels and led by instructors with vast amounts of experience

$170 $65

Chicago Bulls Game for Two and Optional Memorabilia Signed by Jimmy Butler or Dennis Rodman (November 7–March 10)

Official Fan Package

United Center

Seasoned vets Rajon Rondo, Dwyane Wade, Jimmy Butler, and Robin Lopez take the court against NBA opponents

$181 $69

$20 for 30 Kickboxing and Fitness Classes from FIGHT2FITNESS ($299 Value)


Multiple Locations

30-class pass allows students of all ability levels to gain access to a variety of fitness and Kickboxing classes at various locations

$299 $20

Five or Ten Kickboxing Classes at Kickboxing Beverly (Up to 86% Off)

Kickboxing Beverly

Multiple Locations

Punch, kick, and jab your way to fitness, reduce stress, and learn self-defense in these calorie-burning kickboxing classes

$90 $15

5 or 10 Kickboxing Classes at Kickboxing Stoney Island (Up to 86% Off)

Kickboxing Stoney Island

Multiple Locations

Participants kick and punch their way through a full-body workout

$90 $15

Bowling Package for Two, Four, Six, or Eight at Skyway Bowl and Sports Bar (Up to 50% Off)

Skyway Bowl and Sports Bar

South Deering

Enjoy cold beers, live music, and the company of friends at this 36-lane bowling alley and sports bar

$30 $15

Two Weeks or One Month of Beginner Jujitsu and Kickboxing at Movimento Fitness (Up to 85% Off)

Movimento Fitness

Central Chicago

Brazilian jujitsu and muay thai kickboxing classes led by a Gracie-trained instructor and a former US Marine Corps squad leader

$130 $25

Two-Hour 21-Ft Electric or 22-Ft Pontoon Boat Rental for Up to 12 People from Vantage Boat Share (Up to 67% Off)

Vantage Boat Share

Vantage Boat Share

Luxury 21-foot electric boats or 22-foot pontoon boats host up to 12 guests in two-hour tours of area waterways

$250 $99

Indoor Golf Lesson with Option of Driving or Putting, or Kids' Lesson at Golf in Motion (Up to 73% Off)

Golf in Motion


Adults and kids take golf lessons that focus on the fundamentals of the sport; adults can also focus specifically on driving or putting

$240 $65

Kung Fu, Kickboxing, Boxing, Brazilian Jiu-jitsu, MMA, and Taichi Classes at EKF Martial Arts (Up to 62% Off)

EKF Martial Arts


Learn Kung Fu from Mortal Kombat’s real-life Kung Lao, Anthony Marquez, or blend martial arts styles in MMA classes

$65 $29

5 or 10 Kickboxing Classes at Kickboxing Kedzie (Up to 86% Off)

Kickboxing Kedzie

Multiple Locations

Kickboxing classes teach self-defense techniques during full-body workout

$90 $15

$99 for an Eight-Week Soccer Program for One Child from West Loop Soccer Club ($160 Value)

West Loop Soccer Club

Near West Side

Boys and girls aged 2–12 learn soccer basics, including ball control and coordination, and the importance of teamwork and good character

$160 $99

Four Classes or One Month of Unlimited Classes at Shinjinkai, The Japanese Martial Arts Society (Up to 75% Off)

Shinjinkai, The Japanese Martial Arts Society


Instructors guide students of all levels through martial arts classes such as youth aikido, weapons classes and modern martial arts

$75 $19

5 or 10 Jiu-Jitsu Classes at Redzovic Jiu-Jitsu Lincoln Park (Up to 82% Off)

Redzovic Jiu-Jitsu Lincoln Park


From the merchant: Can you defend yourself against an attacker? Come learn the world’s most effective martial art: Gracie Jiu-Jitsu

$100 $19

One Swing Evaluation, One Lesson, or Three Lessons at Gabe Rios Golf (Up to 55% Off)

Gabe Rios Golf

Gabe Rios Golf

Relaxed and fun golf lessons inside hitting bay with Foresight launch monitor, V1 Golf video analysis, two big screen TVs & a real sand trap

$100 $45

$20 for $36 Worth of Bicycle Rental — ChainLinks


Far North Side

Walk in and bike out! Rent a bike for a day and enjoy summer time in Chicago. Groupon valid for new customers only.

$36 $20

5 or 10 Classes for Adults or Kids with a Uniform at Hyun's Hapkido and Tae Kwon Do Schools (Up to 69% Off)

Hyun's Hapkido and Tae Kwon Do Schools


Adults or kids don uniforms and join peers in Hapkido or Tae Kwon Do martial arts classes at a school that's served Chicago since 1971

$240 $79

Up to 79% Off Martial Arts Classes at Andre Maneco Brazilian Jiu Jitsu

Andre Maneco Brazilian Jiu Jitsu

West Town

From the merchant: Get in great shape while learning proven techniques with world class quality martial arts

$140 $30

One Month of Saturday Basketball Camp for One Child at DATSWZUP (Up to 60% Off). Three Options Available.


Tuley Park

Basketball camp run by Norrice Quarles pays equal mind to basketball fundamentals, physical fitness, and skills such as reading

$50 $20

$49 for One Month of Kids' Martial Arts Classes at Kensho Martial Arts ($197.25 Value)

Kensho Martial Arts


Kids build focus and confidence through self-defense

$197.25 $49

Two Weeks or One Month of Unlimited Martial-Arts Classes at The Warrior Institute of Chicago (Up to 67% Off)

The Warrior Institute of Chicago

The Warrior Institute of Chicago

Classes help children develop basic coordination skills and learn self-confidence, while adults can tone their bodies and learn self-control

$119 $39

One or Three Months of Kickboxing Classes at US Martial Arts (Up to 76% Off)

US Martial Arts

Multiple Locations

Kickboxing classes teach self-defense techniques during intense calorie-burning full-body workout

$140 $39

Select Local Merchants

  • Go Sailing Chicago
    Gliding across Lake Michigan, the sailing party watches the sun sink beneath the Chicago skyline. As the last rays fade from view, the city's skyscrapers throw their light onto the lake's surface. The captain steers the ship past Grant Park and Millennium Park, and then veers out toward Navy Pier, where the ship's passengers find a prime viewing spot for the Saturday-night fireworks show. In addition to charters like these, the captains of Go Sailing Chicago—all holding US Coast Guard Master Captain licenses and certifications from the American Sailing Association and US Sailing—furnish beginner through advanced sailors with sailing gloves and life jackets before leading hands-on instruction in proper seamanship. Launching from DuSable and Monroe Harbor, and sometimes other points along the lakeshore, Go Sailing Chicago's four-boat fleet meets or exceeds the safety standards set down by the USCG and the most persnickety of ship-in-a-bottle builders.
    Read More
    Chicago, IL US
  • Tall Ship Windy
    The massive schooner gently bobs in the Lake Michigan waters as the Chicago skyline towers on the shore. Onboard, hardy sailors relate tales of piracy as they train their passengers to tie knots and unfurl sails. Period lessons abound onboard Windy, the lone vessel helmed by US Coast Guard-certified captains and crews. The nostalgic steed is used to educate visitors on the lake's maritime traditions and explore coastal waters. Windy also plays host to themed adventures that include fireworks shows, pirates explaining city architecture, and pirates complaining about the popularity of pool noodles. Crews strive to make each tour unique, with sailors who expound on their skills as well as performers and educators versed in history, maritime lore, art, and theater.
    Read More
    Chicago, IL US
  • Chicago Line Cruises
    Sometimes all it takes is a suggestion. Terry Johnson and Paul McCarthy founded their vessel-chartering business in 1980. But when a good friend recommended they offer expertly narrated tours on the history and the iconic architecture of Chicago, the pair jumped at the opportunity. Praised as the “Best architecture tour available” by the Chicago Sun-Times and “Most engaging tour of the bunch” by Time Out Chicago, their river cruises take passengers on three types of educational, 90-minute tours of the city. Chicago Line Cruises has transported more than three million Chicagoans and visitors along the river for entertainment, stunning views, and a deeper appreciation for architectural design. Architectural Cruises Learn how Chicago became the birthplace of the first buildings to be dubbed "skyscrapers." Hear how the Great Chicago Fire paved the way for an architectural renaissance. See a broad selection of modern architectural styles and discover the distinctive characteristics of each. Experience Chicago's first architectural river cruise. Historical Cruises Hear the overarching story of how Chicago transformed from a swampy marshland to a world-class city. Learn about the Chicagoans whose innovations helped influence architecture and commerce around the world. Savor a cup of Starbucks coffee while a guide recounts Chicago's triumphant and tragic moments. Historical tours are presented in partnership with the Chicago History Museum. Chartered Cruises Private outings are available for 20–173 passengers. Full-service bars and professional sound systems are available for special events. Celebrate while savoring views of the Chicago skyline from a different perspective. Choose from three vessels: the Ft. Dearborn, the Innisfree, and the Marquette.
    Read More
    Chicago, IL US
  • Millennium Sailing
    What services does your business offer and what makes your business stand out from the competition? Large, comfortable, 40 ft pristine luxury sailing yacht; fully equipped with everything you need for your party including 2 bathrooms, refrigerator, serviceware, grill, pool toys, and play your own music with an iPod connection. Ice and water is also included. What is the experience customers can expect? Amazing views of the city skyline. Experience the quiet motion of the boat under sail and even take the helm if desired. Captain shares knowledge of local city history & architecture. Watch transformation from daylight to city lights on evening cruises. A safe, fun, memorable summer experience! What was the inspiration to start or run this business? After 30 years of sailing experiences while raising my family and entertaining friends on our sailboat, I wanted to share my love of sailing with others. What do you love most about your job? Sailing itself while making a boat move only under the power of the wind and sails, stimulating conversations with clients, Entertaining guests with humor and knowledge with personal stories while sharing information about the skyline and Chicago history and watching clients enjoy themselves!
    Read More
    Chicago, IL US
  • Carefree Boat Club Chicago
    Carefree Boat Club was founded on the principle that adventuring on a boat is always more fun without the chores associated with ownership. Over time, the owners gathered a huge fleet of speedboats, pontoons, and sailboats, launching them into prime boating waters from 27 harbors around the nation. They also assembled a team of maintenance experts to care for the vehicles, removing cleanup and repair responsibilities from club members' agendas. Then, they set their membership rules, keeping a strict ration of ten members to every one vehicle in their fleet to ensure easy boating access. Today, the company maintains a fledgling branch of their operation out of the 31st Street Harbor in Chicago. Their growing fleet already includes a variety of speed boats ready to zip across the smooth surface of Lake Michigan, such as the Sea Ray 240s, 260s, and 270s. In addition to providing unlimited vessel access for members and rentals for non-members, they also arrange a variety of club events at each location. Members go on annual picnics, gather together on holidays, and host seminars for boating-related subjects such as safety, navigation, and how to trick everybody into calling you admiral.
    Read More
    Chicago, IL US
  • Come Sailing, Inc.
    When you're with Bernard, you're sure to see Chicago's lakefront from some incredible angles. Bernard is kind of like a tour guide, though she's not actually a person—she's the largest boat in Come Sailing's fleet. From her spacious deck, passengers soak up views of the skyline, fireworks, and dazzling Midwest sunsets. Of course, Bernard can't operate solo. She relies on Come Sailing's owner, Captain Mike, to help her cruise across Lake Michigan. Before you climb aboard, here are some things to know about your captain: Qualifications: Captain Mike is a US Coast Guard-certified charter captain. He grew up sailing the waters of Lake Michigan with his dad. How he met Bernard: Captain Mike spent many summers sailing in Wisconsin and Michigan, and finally, he decided to purchase his own 36-foot Catalina. Accomplishments: While he loves sailing with others—including his wife and daughter—Captain Mike is an accomplished solo sailer, too, and he's completed numerous long-distance voyages.
    Read More
    Chicago, IL US