Tours in North Side

Up to 50% Off Ultimate Barcrawl Challenge

Ultimate Barcrawl Challenge

Deuce's

$15 $8

Goldfish races, relay races, and other drinking games are held at four Wrigleyville bars

Up to 57% Off Social Game Experience

Waxwing Puzzle Co.

Logan Square

$40 $20

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Players take part in a role-playing event that is set in the prohibition era and pulls from mob folklore

Up to 55% Off Arcade Tournament League

BUCKit List Events

Multiple Locations

$80 $39

Three-person teams go head-to-head in seven-week arcade tournament with one week of playoffs

Up to 51% Off an After-Work Cruise

ChicagoCruiseTickets.com

Chicago

$25 $13

Cruises aboard a yacht with dance floors and bars provide brilliant evening views of the Chicago skyline

Up to 52% Off Chicago Sports Tour

Chicago Sports Tours

Chicago

$42 $21

Saturday sports tours explore Chicago's rich history of football, baseball, basketball, and hockey

Up to 38% Off from Weird Chicago Tours

Weird Chicago Tours

Near North Side

$60 $39

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Travel by bus to the former crime scenes, red-light districts, gangster hangouts, or ghost-sighting spots of Chicago's storied past

Up to 53% Off from Chicago Crime Tours

Chicago Crime Tours

Chicago

$79.90 $38

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

Up to 56% Off Pizza Walking Tour

Slice of Chicago Pizza Tours

Near North Side

$90 $42

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2-hour, 1.2-mile walking tour hits Pizzeria Uno, Pizzeria Ora, and Giordano's in River North to sample deep-dish pizza and learn its history

Up to 60% Off the Great Food Tour of Chicago

Great Food Tours

Chicago

$50 $25

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

Tour Chicago's Moving Bridges with a Civil Engineer

Moving-Bridge Tour

The Loop

$20 $20

Retired Civil Engineer Jim Phillips expands on the how and why of Chicago's moving bridges during a tour by foot and water taxi

50% Off Deluxe Wine Tour for Two or Four

Windy City Wine Tours

Near North Side

$800 $398

Groups up to 10 tour midwest wineries while learning the history and bakground of each vineyard and its wine

Up to 52% Off True Crime and City Highlights Tour Bundle

Chicago Prime Tours

Chicago

$66 $34

Hear the stories of John Dillinger, John Wayne Gacy. and H.H. Holmes during crime tour, and visit Willis Tower and other sites on city tour

Up to 52% Off Chicago Sightseeing Tours

Chicago's Finest Tours

Multiple Locations

$60 $29

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Tours take guests along Chicago's historic River Walk, into jazz clubs, or to a hearty brunch buffet

55% Off Scavenger-Hunt Adventure Race

The Ultimate Urban Scavenger Race

Lizzie McNeills Irish Pub

$55 $25

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

Up to 47% Off Loop Interior Architecture Tour for Two

Chicago Detours

Chase Tower

$52 $29

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Featured in the Chicago Reader, guides lead groups through architecturally striking interiors and share photos and videos via iPads

Up to 33% Off a Sailing Tour on Tall Ship Windy

Tall Ship Windy

Navy Pier

$30 $20

A 148-foot-long, traditional four-masted schooner sails throughout Lake Michigan for about 75 minutes

Up to 55% Off Chicago Architecture Walking Tour

Inside Chicago Walking Tours

On Location

$20 $10

A former teacher and improv comedian offers a slice of Chicago architecture during engaging walking tour

Chicago Architecture Foundation – $13 for a "Must-See Chicago" Tour

Chicago Architecture Foundation

Chicago

$20 $13

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Stroll past such Chicago icons as the Art Institute, Willis (Sears) Tower, Wrigley Building, Chicago Theatre, and John Hancock Center

Up to 78% Off from TikiBoat Chicago

TikiBoat Chicago

Monroe Harbor

$1,799 $399

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36-foot party barge with water slide ferries guests onto Lake Michigan and Chicago River; amenities include stereo, grill, and full bathroom

50% Off a Quincy Street Distillery Tour

Quincy Street Distillery

Riverside

$44 $22

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

Up to 51% Off a Helicopter Tour of Chicago

Chicago Helicopter Express

Wheeling

$360 $199

Helicopters cruise 800 feet above the Chicago skyline past such famed sights as Willis Tower, Wrigley Field, and Navy Pier

41% Off a Stunt-Airplane or Warplane Ride

Gauntlet Warbirds

Sugar Grove

$440 $259

A seasoned flight instructor leads a 40-minute joy ride aboard an Extra 300L aerobatic plane or a T-6 Texan warplane

Select Local Merchants

Walking is one of the best ways to get to know a city. It forces you to move slowly, taking in every weathered brick, intriguing alleyway, and door marked with the sign "Do Not Look At This Door." There's also a good chance it will lead to adventure. At least, that's the belief at the heart of Stinky Onion Tours' walking excursions. With a love of walking rivaled only by local pride––as evidenced by the company's name, a nod to the legendary mistranslation that gave Chicago its name––the company uncovers forgotten moments in Chicago's past through a combination of food and historical fact. Tours include Truckin' Along, which introduces the history of the city's food trucks and makes stops for a bite at several. Hobohemia explores the city's long-ago hobo and bohemian culture, and the Old Town tour winds through the historic venues and restaurants of the neighborhood of the same name.

Unknown
Chicago,
IL
US

Chicago Elevated, run by effusive improv veteran Margaret Hicks, leads curious charges on eclectic group, private, and custom tours of the city. Jaunts lead natives and tourists alike through the city’s oft-overlooked nooks and crannies as Hicks’s jovial voice narrates every step, shedding light on secret areas and easily overlooked historic sites. Her pedway tour sojourns into Chicago’s tiled subterranean antecity, where retailers, restaurants, and mole people mingle. Tours explore sites of famous disasters, visit the ghostly red-light district that once stretched below what is now Printer’s Row, and gaze at downtown’s ornate architecture from the riverwalk.

Stationed in Wrigleyville after college, Hicks accrued the healthy sense of humor and comedic timing that pepper each tour at Second City, iO, and other theaters. Though she attempted a move to New York City, Hicks soon discovered she couldn’t stay away from Chicago’s majestic skyline or the skyscrapers’ subtly receding hairlines. A stint in the Chicago Architecture Foundation’s docent program, as well as acting as a tour guide for six years, arm her with insider’s knowledge that soon transfers to listeners’ brains.

4870 N Paulina St
Chicago,
IL
US

Helmed by husband-and-wife team Al and Sima Bovali, Corner 41 Bar and Grill welcomes diners with a stylish, homespun ambiance. From an open kitchen, wafts of gourmet American fare escape pans to greet guests at their tables, where menus harbor the tasty details of elegant entrees, burgers, and sandwiches. Exposed-brick walls unify with dark hardwood floors to augment the restaurant's intimate airs, and high ceilings create an acoustically sound backdrop for rustic ducts and yodeling chandeliers. Diners can also enjoy sips from a favorite wine, draft beer, or martini, and midnight closing times on the weekends accommodate late-evening munchers.

4138 N Lincoln Ave
Chicago,
IL
US

Simply put, Players Sport & Social Group helps more than 60,000 people each year get together, meet new friends, and have fun. The two-decade-old company has more than doubled in size in the last five years, due in no small part to the wide variety of sports leagues and clinics that it offers at venues throughout the city. Teams or individuals can sign up for sports ranging from dodge ball to beach volleyball to games of "bags," otherwise known as cornhole. Players can check their weekly standings online and review each sport's rules, learning exactly what is considered a foul in kickball or how to dispose of a football opponent's captured flag by burning it in a respectful ceremony.

The company also hosts and sponsors social events such as happy hours, fundraisers, and the Luau: a 55,900-participant grass-volleyball tournament with DJ music, food, and beer. Similarly, The Big Dig volleyball tournament offers the same mix of munchies, brews, and live entertainment, but on the sands of North Avenue Beach.

3617 N Ashland Ave
Chicago,
IL
US

When winter weather blows its way in off the lake each November, a Cubs parking lot situated in the shadow of Wrigley Field transforms into a full-size ice-skating rink, which remains in operation until the beginning of March. There, guests glide atop glistening steel blades, twirling around the icy expanse while taking in views of Wrigley Field’s iconic exterior and extremely delayed fly balls.

1060 W Addison St
Chicago,
IL
US

Established: 2013
Reservations/Appointments: Required
Staff Size: 2–10 people
Average Duration of Services: 1–2 hours
Pro Tip: Wear comfortable shoes and dress for the weather.
Handicap Accessible: No
Most Popular Attraction/Offering: Chicago's architecture, 1880s thru today
Recommended Age Group: All Ages

Q&A with Hillary Marzec, Owner and Tour Guide

What is the one feature of your business that you're most proud of?
The quality of my tours. I know from several years of experience, being told by [hundreds] of people (meeting thousands of people each season), that my way of organizing and delivering information is not only very engaging, entertaining, and interesting, but also -- and this is important for me as a former teacher -- very graspable and memorable for all ages. I'm very good at making information interesting to any "students," young to old.

Is there anything else you want to add that we didn't cover?
[I have a] passion for this subject and for teaching about this subject, and entertaining people in the process. People should learn, but enjoy it so much, the learning happens almost subconsciously.

2240 West Farragut Avenue
Chicago,
IL
US

North Side Scene