Helicopter Ride in Chicago, IL

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

Bachman Aero


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

General Admission for One, Two, or Four to The Skydeck at Willis Tower (23% Off)

The Skydeck at Willis Tower

The Loop

Interactive exhibits, a theater presentation, and an elevator ride lead to a 1,353-ft. glass skydeck with views of the city—and four states

$22 $17

25% Cash Back at Duffy's Tavern and Grille

Duffy's Tavern and Grille

North Side

Claim this deal and get 25% cash back rewards when you pay with your linked Visa card at Duffy’s Tavern and Grille

$0 $0

Halloween Bar Crawl on October 28 or 29

Halloween Trolley Bar Crawl or Halloween Bar Crawl: Crawl-o-ween

Multiple Locations

Don creative Halloween costume, then walk to Chicago bars featuring drink specials, scavenger hunts, and prizes

$17.36 $8

24- or 48-Hour Passes to Guided Tours from Chicago Trolley & Double Decker Co. (Up to 29% Off)

Chicago Trolley & Double Decker Co.

Multiple Locations

Guides narrate sights of the Windy City as double deckers cruise to multiple stops downtown with “hop on hop off” access

$45 $32

A Nightmare on Hubbard Street-The 5th Annual River North Halloween Costume Bar Crawl on Saturday, October 29, at 12 pm

A Nightmare on Hubbard Street – The 5th Annual River North Halloween Costume Bar Crawl

Bar Louie

Annual Halloween-themed bar crawl weaves through River North, with drink specials, live DJs, and a costume contest along the way

$27.95 $15

Visit for One, Two, or Four to the Chicago History Museum (50% Off)

Chicago History Museum

Chicago History Museum - Live

Chicago museum brings history to life with 22 million artifacts & topical exhibits, including a look at railroad workers during WWI

$16 $8

Gangster Tour of Chicago for One, Two, or Four from Best Tours (Up to 65% Off)

Best Tours (Chicago)

Best Tours (Chicago)

Tour-goers take a 90-minute jaunt past iconic landmarks and mob movie filming locations while learning about Chicago’s gangster past

$35 $17

Cupcake Tour of Chicago with Six Tastings for One, Two, or Four from Best Tours (Up to 68% Off)

Best Tours


Tours make six stops along Michigan Avenue, visiting a century-old shop, one with 50 varieties of cupcake, and another with gelato

$50 $19

Distillery Tour and Souvenir Shot Glasses for Two or Four at Koval Distillery (Up to 42% Off)

Koval Distillery


Award-winning producers of organic and kosher whiskeys give a glimpse of their process on a tour that includes souvenir shot glasses

$30 $19

Riverwalk Food Tour of Chicago for One, Two, or Four from Best Tours (Up to 60% Off)

Best Tours (Chicago)

Best Tours (Chicago)

Tours make stops at eateries located along the Chicago Riverwalk and introduce tour-goers to Chicago’s history and famous architecture

$50 $25

Self-Guided Chicago Scavenger Hunt for Two, Four, or Six from Big City Hunt (Up to 54% Off)



Participants gear up and launch the Big City Hunt app to start their own adventure, racing against the clock at a time of their choosing

$40 $22

Great Food Tour of Chicago with Six Tastings for One, Two, or Four from Best Tours (Up to 60% Off)

Best Tours


Tours make six stops along Michigan Avenue, visiting the originator of deep-dish pizza and an eatery serving up Chicago-style hot dogs

$50 $25

Chocolate Tour of Chicago with Seven Tastings for One, Two, or Four from Best Tours (Up to 60% Off)

Best Tours

Wrigley Building

Sample Aztec chocolate drinks, cupcakes, truffles, and chocolate donuts during two-hour chocolate tour along the Magnificent Mile

$50 $25

$37 for a Two-Hour Segway Tour of Downtown Chicago from Segway Experience of Chicago (Up to $65 Value)

Segway Experience of Chicago

Segway Experience of Chicago

Atop a latest-generation Segway PT, guests coast past Buckingham Fountain and Museum Campus, occasionally pausing for photo ops

$65 $37

Drunk History Tour of Chicago at Four Pubs for One, Two, or Four from Best Tours (Up to 60% Off)

Best Tours


Visit four local pubs to sample alcoholic beverages and shots, learn about the history of the city, and pick up some fake history too

$50 $25

Free Kids' Event: Free Weekends Fiddleheads

Free Kids' Event: Fiddleheads

Garfield Park Conservatory

Families with young kids participate in nature-themed projects at the conservatory; the Halloween event features animals, including a sloth

$0 $0

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

River North Wine Fest - Saturday December 3, 2016 / Noon to 4:00pm

Moe's Cantina and Old Crow Smokehouse River North

Near North Side

$50 $28

Wine & Cheese Tour of Chicago with 12 Tastings and Pairings for 1, 2, or 4 from Best Tours (Up to 58% Off)

Best Tours

Best Tours

Stroll along the Magnificent Mile and through the Gold Coast as you sample 12 bites of cheese paired with sips of wine

$100 $49

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

Two or Four Admissions at Weird Chicago Tours (Up to 39% Off)

Weird Chicago Tours

Pick up location

Tour guides take guests on three-hour tours of Chicago to see the city’s most haunted spots and historical landmarks

$70 $45

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

"Death Toll": A Halloween Drinking Game Performance

The Cornservatory

North Side

$10 $7.50

Three-Hour Fright Hike Bike Tour for One or Two from Bobby's Bike Hike (Up to 50% Off)

Bobby's Bike Hike


Bike tours explore Chicago’s most ghoulish sites, like Resurrection Mary’s haunts and the riverside site of the deadly SS Eastland sinking

$49 $25

Pizza Tour of Chicago for One, Two, or Four from Best Tours (Up to 60% Off)

Best Tours (Chicago)

Best Tours (Chicago)

Guest stroll past famous Chicago landmarks on their way to the city’s best pizza joints for samples, demos, and history lessons

$50 $22

Italian Food Tour of Chicago with Five Tastings for One, Two, or Four from Best Tours (Up to 60% Off)

Best Tours

Best Tours

Sample Chicago-style pizza, italian beef, and artisan products during a two-hour Italian-food tour along the Magnificent Mile

$50 $25

Walking Food Tour for One or Two from Sidewalk Food Tours of Chicago (Up to 37% 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 $35

90-Minute Brewery Tour for Two, Four, or Six with Tastings, Snacks, and Glasses at Argus Brewery (Up to 57% Off)

Argus Brewery

Far Southeast Side

During a 90-minute tour, guests learn about the historic origins of the brewery and the neighborhood while sampling craft brews

$30 $15

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.
    Read More
    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.
    Read More
    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.
    Read More
    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.
    Read More
    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.
    Read More
    Wheeling, IL US