Helicopter Ride in Chicago, IL


$149 for a Helicopter Flying Lesson and Flight from Bachman Aero ($325 Value)

Bachman Aero

Schaumburg

The 30-minute helicopter flying lesson puts students in control of the craft at 500 feet with instruction from a FAA Certified Pilot

$325 $149

Luxury Downtown Chicago Helicopter Tour for up to Three People from AM Air Service (Helicopter Tour)

AM Air Service (Helicopter Tour)

Schaumburg Regional Airport-Hangar C28

45-Minute helicopter tour over downtown Chicago takes passengers over landmarks such as Willis Tower, Hancock Building, and Navy Pier

$549 $499

Fireworks Paddle

Kayak Chicago - Chicago River

Goose Island

$75.21 $45.11

City Lights Night Paddle

Kayak Chicago - Chicago River

Goose Island

$64.31 $38.91

Tour by Bus for Two or Four from Chicago Crime Tours (Up to 38% Off)

Chicago Crime Tours

Near North Side

Learn about more than 100 years of Chicago’s crime history in a 90-minute tour of famous crime scenes and landmarks

$159.80 $99

$75 for a Lazy River Tubing Outing with Round-Trip Transport from Cannonball Productions ($93.65 Value)

Cannonball Productions

Bus Pick-Up

Enjoy a day of river floating and an afternoon at the park, basketball, slip n’ slide, volleyball, and an all-you-can-eat taco bar

$93.65 $75

Choice of Ghost Bus Tour for One or Two at Chicago Hauntings Ghost Tour (19% Off)

Chicago Hauntings Ghost Tour

Chicago Hauntings Ghost Tour

Paranormal experts narrate a bus tour; specialty tours explore haunted sites inspired by the city’s gothic past or the notorious H.H. Holmes

$36 $29

Sightseeing Tour or Brunch Tour for One or Two from Chicago's Finest Tours (Up to 52% Off)

Chicago's Finest River Walk Tour

Wrigley Building Plaza

Tours take guests along Chicago’s historic River Walk, around the Loop, or to a hearty brunch buffet

$50 $24

$59 for a Three-Hour Segway Tour of Chicago from City Segway Tours ($70 Value)

City Segway Tours (Chicago)

City Segway Tours Chicago

Take a guided Segway tour past Chicago landmarks including Soldier Field and the Field Museum, and enjoy views of Navy Pier and the skyline

$70 $59

Walking Food Tour for One or Two from Sidewalk Food Tours of Chicago (Up to 40% Off)

Sidewalk Food Tours of Chicago

Wicker Park

Enjoy a roving lunch of five different tastings while learning about the history and culture of either River North or Wicker Park

$55 $34

$39 for a Two-Hour Wednesday-Night Fireworks Cruise from Island Party Boat ($75 Value)

Island Party Boat

Chicago Lakefront

Take in fireworks lighting up the Chicago skyline on an island-themed 50-foot boat equipped with a sundeck, lounge, and premium sound system

$75 $39

Chocolate Crawl for One, Two, or Four from Second City Tours (Up to 60% Off)

Second City Tours

Water Tower Place

Get your chocolate fix during this tour that visits five of the city’s most beloved sweet-treat havens

$50 $23

Chicago Chinatown Walking Tour for Two or Four from the Chicago Chinese Cultural Institute (Up to 52% Off)

Chicago Chinese Cultural Institute

Armour Square

Chinatown walking tour showcases historical landmarks and great restaurants and teahouses on a 90-minute, 5- to 6-block jaunt

$20 $10

One, Two, or Four Tickets to the Chicago Gangster Tour from Second City Tours (Up to 61% Off)

Second City Tours

Holy Name Cathedral

Guides recount local legends about Al Capone, Dillenger, and more during a 90-minute gangster tour

$30 $14

Gangster History Tour from The Barrel Run (Up to 40% Off)

The Barrel Run

Near North Side

A bus styled to look like an actual beer barrel sets a party-friendly tone for these educational tours of Chicago’s gangster-filled history

$70 $49

$25 for Entry to Chicago Challenge: The Ultimate Urban Scavenger Race on Saturday, July 9, 2016 ($55 Value)

Challenge Nation

Municipal Bar & Dining Co.

Teams race to solve clues and strategize to win cash prizes and awards during urban race; music and drink specials at post-race party

$55 $25

Lake Paddle

Kayak Chicago - North Avenue Beach

North Side

$75.21 $45.11

Pizza Parade Tour for One, Two, or Four from Second City Tours (Up to 60% Off)

Second City Tours

Chicago

Guides will lead you through River North to sample pizza from local eateries, including the original Uno Pizzeria & Grill

$50 $23

Cupcake Crawl for One, Two, or Four from Second City Tours (Up to 60% Off)

Second City Tours

Water Tower Place

The city’s favorite cupcake hot spots are visited during this tour: Sprinkles, Sacred Grounds, More, and Crumbs

$50 $23

24- or 48-Hour Adult Ticket for a Hop On, Hop Off Chicago Bus Tour from Big Bus Tours

Big Bus Tours

Michigan Ave

Narrated double-decker bus tour of Chicago sights; hop on and off at your leisure, with discounts and free treats at local businesses

$40 $40

Sidewalk Food Tours of Chicago: Wicker Park

Wicker Park

Bucktown

$55 $43.75

Chicago Food Crawl for One, Two, or Four from Second City Tours (Up to 60% Off)

Second City Tours

Near North Side

Head to River North for deep-dish pizza, Chicago-style hot dogs, Mike Ditka’s favorite italian-beef sandwiches, and dessert

$50 $23

Ghost Tour for One, Two, or Four from Second City Tours (Up to 61% Off)

Second City Tours

John Hancock Center

90-minute tour explores the tragic side of Chicago history with stops to locales said to be marked by paranormal activity

$30 $14

Chicago Pizza Walking Tour for Two or Four from Slice of Chicago Pizza Tours (Up to 44% Off)

Slice of Chicago Pizza Tours

Near North Side

2-hour, 1.2-mile walking tour hits several pizzerias like Pizzeria Uno and Giordano’s in River North to sample pizza and learn its history

$100 $60

One, Two, or Four Tickets to Belmont Food Binge Tour from Second City Tours (Up to 60% Off

Second City Tours

Lakeview

Enjoy Lakeview’s ethnic- and American-food offerings, including tacos, French pastries, falafel, and grilled cheese

$50 $23

Notorious Chicago Crime Walk for One, Two, or Four from Second City Tours (Up to 61% Off)

Second City Tours

John Hancock Center

90-minute tour explores the sites and shares the stories and secrets behind Chicago’s most infamous crimes

$30 $14

Three-Hour Walking Food Tour for One or Two from Sidewalk Food Tours of Chicago (Up to 26% Off)

Sidewalk Food Tours of Chicago

Multiple Locations

Local guides talk about the architecture and history of River North or Wicker Park while stopping at places such as Xoco and Antique Taco

$55 $42

One, Two, or Four Tickets to the Burger & Beer Binge Food Tour from Second City Tours (Up to 59% Off)

Second City Tours

Near North Side

Explore three River North hotspots and sip craft beers paired with specialty burgers

$100 $49

One, Two, Three, Tickets to a Chicago Sweet Treats Tour from Second City Tours (Up to 56% Off)

Second City Tours

Second City Tours

Guests sample cupcakes, cake balls, truffles, and gelato and a number of famous Chicago sweets shops on this 90-minute tour

$50 $25

"Sherlock Holmes and the Mystery of Portage Park"

Filament Theatre

Portage Park

$20 $15.50

Select Local Merchants

  • Chicago Helicopter Experience
    Chicago is famous for its skyline, but there's only so much sky you can see from the ground. That's why at Chicago Helicopter Experience, pilots lift passengers from Chicago's first private heliport, to enjoy the view of downtown's busy streets and wide-open views of the city's magnificent architecture. Three types of tours each afford a unique experience, whether it's seeing the sunset reflecting off the Willis Tower or cruising over the nocturnal landscape of the city. Each tour takes place within the state-of-the-art EC130 helicopter, which features plush leather seats, noise canceling headsets, and bubble windows with a panoramic 180° view outside.
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    2420 South Halsted Street
    Chicago, IL US
  • Sun Aero Helicopters Inc.
    The pilots at Sun Aero Helicopters Inc. have been training pupils in the autogiro arts and transporting clients through the skies since 1991. Inside their base at Lansing Municipal Airport, aviators maintain a 12,000-square-foot hangar area and 3,000 square feet of training offices and high-speed computerized flight-planning facilities. Expert pilots impart their knowledge to up-and-coming FBI agents, police officers, emergency medical technicians, and leisure pilots during one-on-one training sessions in Robinson and Bell copters. Pilots also give landlubbers a skyscraper's view of Chicago's landmarks, such as US Cellular Field, the John Hancock building, and the Sears/Willis Tower. When they aren't transporting rally drivers, golfers, and famous wiffle ball players with private charter services, Sun Aero serves national media companies with aerial photography and land surveys.
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    160 Robert T Palmer Drive
    Elmhurst, IL US
  • A & M Aviation
    Sunlight radiates off the pair of 30-foot, brilliant-yellow wings that frame A & M Aviation’s 1942 WACO UPF-7 biplane as it rests on the tarmac at Clow International Airport. A pilot starts the vintage bird's 220 hp Continental engine, and the propellers begin to spin, quickly disappearing into a heart-quickening blur as the plane lurches forward. One of fewer than 80 still in existence, the plane was used as a trainer for US soldiers before they shipped off to fight overseas. Today, after a full restoration in 2003 that returned it to its youthful glory, civilian passengers are transported to those proud days as they sit side-by-side in the biplane’s spacious open-air cockpit behind a windscreen that protects their faces from flying bugs and raspberries from passing beagles. Thanks to the careful executions of the pilot in front of them, they watch the ground slowly pull away as the biplane carries them anywhere within a 25-mile radius of the airport, whether that be a low buzz over the downtown lakeshore or a leisurely cruise over nearby farms, forests, and Midwestern expanses.
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    130 S Clow Int. Pkwy.
    Bolingbrook, IL US
  • Midwestern Helicopter
    Having honed his aviation skills in helicopter cockpits for 45+ years, the head pilot at Midwestern Helicopter leads a team of FAA–certified pilots in performing helicopter tours, charters, and pilot instruction. They steer a fleet of three Robinson R-44s and two R-22s over cityscapes and country vistas with photographers, pollinators, surveyors, or sightseers onboard, continuing a crash- and speeding-ticket-free record begun with the company's inception four years ago. The flight team acquaints new flyers with immediate actual flight experience during introductory flights and helps students to achieve private, commercial, and flight-instructor certification during FAA courses. As authorized merchants of Robinson aircraft, they can also hawk helicopters or perform maintenance on various models inside heated hangars without having to first notify the aircraft's next of kin.
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    1071 South Wolf Road
    Wheeling, IL US
  • Chicago Helicopter Tours
    Lifting off from Palwaukee/Chicago Executive Airport, Chicago Helicopter Tours provides passengers with a bird's-eye view of the Windy City and its abundant scenery on Lake Michigan's shores. Depending on the tour selected, the chopper might fly high over the North Shore, Northwestern University and the Bahá'í Temple, soar above the lakefront to Lincoln Park, Wrigley Field, and Montrose Beach, or give passengers the more extensive Grand Chicago Tour. Landmarks to see on the downtown and lakefront tours may include Willis Tower, Soldier Field, Navy Pier, and the John Hancock building. Custom tours are available for photographers and architects.
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    Chicago Executive Airport
    Wheeling, IL US

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