Sightseeing & Tours in Oak Park, IL

Halloween Bar Crawl on October 28 or 29 or Trolley Bar Crawl: Crawl-o-ween on October 29, at 8 p.m.

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

Multiple Locations

Don creative Halloween costume, then walk or hop on a trolley to hit Chicago bars featuring drink specials, scavenger hunts, and prizes

$17.36 $8

VIP Admission for One or Two to the Midnight Terror Haunted House (Up to 46% Off)

Midnight Terror Haunted House

Midnight Terror Haunted House

VIP ticket holders skip straight to the front of the line at this haunted house; inside, 30 terrifying rooms await fright-seekers

$35 $19

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

One Haunted House VIP or Regular Ultimate Ticket at Dungeon of Doom (Up to 20% Off)

Dungeon of Doom


Characters such as Dr. Killpatient, Ravage, and Shank the Clown terrify visitors across a 42,000 sq. ft. haunted house

$30 $25

Admission for One, Two, or Four to the Illinois Railway Museum (Up to 50% Off)

Illinois Railway Museum

Evergreen Park

Watch restored antique train cars in operation, then check out memorabilia from the Chicagoland and national rail industries

$14 $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

Two-Hour Walking Ghost Tour of Aurora or Naperville for One, Two, or Four from Haunted Hometowns (Up to 56% Off)

Haunted Hometowns, Corp.

Multiple Locations

Ghost-seekers clutch EMF meters on lantern-lit tours through historic and haunted sites as guides relate tales of local specters

$20 $12

Moonlit Cemetery Tour Admission for One or Two from Afterlife Tours, Inc. (Up to 52% Off)

Afterlife Tours, Inc.

Multiple Locations

Investigate spirits while exploring the historic—and reportedly haunted—landmark of Oakwood Cemetery by moonlight in a guided tour

$40 $20

4-Train-Ride Tickets for Two, Four, or Six at Hesston Steam Museum (Up to 51% Off)

Hesston Steam Museum

La Porte

Ride on miniature and full-size steam trains and explore interactive exhibits devoted to steam power

$34 $20

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

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

Chicago Explorer Pass Includes Admission to Three or Five Attractions from 20+ Options. Pay Nothing at Gate.

Go City Card

Online Deal

Card grants free admission to 3 or 5 Chicago museums, tours, and attractions, chosen from more than 20 options

$72 $64.80

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

Chicago Helicopter Tour for Two in the Daytime or Nighttime from Chicago Helicopter Experience

Chicago Helicopter Experience

South Side

Passengers soar over the skyline, marveling at the Willis Tower, John Hancock Building, and Trump Tower

$296 $275

Brewery Package for 2 or 4 with Beer Flights, Tour, and 32-oz Crowlers at Blue Nose Brewery (Up to 49% Off)

Blue Nose Brewery


New brewery taking the city by storm gives craft-beer lovers a behind-the-scenes look at the brewing process that includes six-beer flights

$54 $29

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

Brewery Tour Package for Two at Miskatonic Brewing Company

Miskatonic Brewing Company


Take a Sunday-afternoon tour of the brewery, enjoy a couple pints, and head home with your own pint glasses and an unfilled growler

$38 $25

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

Petting Farm and Animal Park Admission for Two, Four, or Six to Jo-Don Farms (40% Off)

Jo-Don Farms


Guests greet more than 200 animals, from camels to tigers, at zoo open for 40 years

$20 $12

$15 for a Brewery Tour for Two or Four with Beer at Penrose Brewing Company ($20 Value)

Penrose Brewing Company


Learn about the Geneva brewery’s craft-beer brewing process and sip two 12 oz. beers

$40 $29

$20 for a Distillery Tour for Two with Two Glencairn Glasses at Quincy Street Distillery ($44 Value)

Quincy Street Distillery

Quincy Street Distillery - Chicago Suburbs

60- to 90-minute tour of a distillery that produces 12 artisanal, small-batch spirits; each guest brings home a Glencairn glass

$44 $20

Visit to a Haunted Military Base for One, Two, or Four at Tour of Terror (Up to 33% Off)

Tour of Terror

Northeast Gary

Visitors tour the spooky Nike Missile Base C-47, a former Army base reclaimed by nature and possibly some disturbed spirits

$15 $10

$8 for Admission to the Night Time Fall Festival on October 28 at Johansen Farms ($13.50 Value)

Johansen Farms


After-dark fall festival celebrates the season with campfires, a corn maze, mini-golf, and access to the zoo with more than 500 animals

$13.50 $8

Wine Tasting for Two, Four, or Six at Downers Grove Wine Shop (Up to 53% Off)

Downers Grove Wine Shop

Downers Grove

Samples of six wines accompany light appetizers during tasting sessions for two, four, or six

$20 $10

$19 for a Wine Flight and Cheese for Two at The Vino Cellar ($36 Value)

The Vino Cellar

South Itasca

Three white or red wine samples accompanied by a cheese plate

$36 $19

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

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

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

Haunted Cornfield, Zombie Paintball, Paintball Target Shoot and Coffin Simulator Rides at Creepy Hallow (Up to 27% Off)

Creepy Hallow

Frankfort, IL

The haunted cornfield and woods of Terror Trails, zombie paintball, and a creepy coffin simulator deliver exhilarating scares

$75 $56

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