Deals in Chicago

Chicago Guide

The nickname "The Second City" was intended as a slight by writer and proud New Yorker A.J. Liebling, but taken another way, it inadvertently captures one of the town's greatest legacies: its ability to rebuild and reinvent itself. The same century that witnessed the burning of Fort Dearborn and the mass destruction of the Great Chicago Fire also saw the completion of the Illinois-Michigan Canal, the arrival of the World's Columbian Exposition, and the building of the nation's first skyscraper. Today, that resilient spirit can be felt throughout the city's diverse neighborhoods, but especially in its bustling downtown.

The pulse of industry and progress beats through The Loop, Chicago's historic commercial center and the country’s second-largest business district. Skyscrapers loom large here, including the Willis Tower (formerly the Sears Tower) and the Chicago Board of Trade. This part of town is also home to award-winning waterfront parks and a glitzy theater district, along with a spectacular array of public art, including outdoor sculptures from Picasso and Joan Miro.

A recent cultural renaissance has seen Chicago's South Loop turn into one of the city's most vibrant residential and industrial centers. Here you'll find some of the buildings that made Chicago one of the world's leaders in architecture in the 1880s and '90s—a title it's held ever since. To the east lies Lake Michigan and the Museum Campus, a 57-acre lakefront park that's home to the city's trio of natural-sciences museums: the Field Museum, the Shedd Aquarium, and the Adler Planetarium.

Just north of the Loop, the Gold Coast neighborhood hugs the shore of Lake Michigan, occupying some of the city's most desirable real estate. The area's reputation as an upscale residential spot dates back to 1882, right after the Great Chicago Fire, when wealthy businessmen began building castle-like mansions along the waterfront––some of which still stand today. The Gold Coast's ritzy legacy is also alive and well at the many clothing stores lining North Michigan Avenue—the so-called Magnificent Mile––and on Oak Street, home to luxury boutiques from designers such as Chanel, Prada, and Hermès.

Simply riding down Lake Shore Drive is an architecture tour in itself, thanks to the superstar skyscrapers lined up along the lakefront. At 18-miles long, the adjoining Lakefront Trail provides an eco-friendly way for runners and cyclists to take in the view. The route also conveniently passes by famous Chicago sights such as Grant Park, Navy Pier, and North Avenue Beach, where crowds gather during the summer to people-watch, play volleyball, and listen to live music at beachfront bars.

The Museum of Surgical Science is one of the hidden gems of Chicago, and it's something that many residents have never seen.
 

Up to 50% Off One-Act Comedy

Mary's Attic

$24.06 $12

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Ensemble presents George Bernard Shaw's one-act comedy of adulterers discovering they've accidentally swapped spouses

47% Off Ice-Dancing Performance

McFetridge Sports Center

$47.04 $25

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World-class figure skaters—including an Olympic Bronze medalist—perform dazzling choreography during the Chicago debut of "Let's Dance"

51% Off Painting and a Play with Wine at Live Purple Art

Chicago

$45 $22

Participants supplied with all-you-can-drink wine paint canvases; actors then interpret the art and brushstrokes in a performance

Up to 51% Off Rooftop Cubs Game

Lakeview

$141.17 $79

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Gaze over Wrigley Field's right-centerfield wall from a luxurious rooftop as the Cubs continue to charge through the 2014 season

The Plagiarists – Up to 53% Off "War Song"

Berger Park Coach House

$26.87 $12.50

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A story of an African-American sergeant in the Civil War comes alive through song, poetry, and writings by W.E.B. DuBois and Lincoln

Wrigley Field Rooftop Club—Up to 65% Off Cubs Game

Wrigley Field Rooftop Club

$185.37 $69

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Watch a Cubs game from rooftop seats overlooking Wrigley Field while enjoying unlimited beer, food, and amenities such as plasma TVs

Gorilla Tango Theatre – Up to 30% Off Burlesque

Bucktown

$70 $49

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Performers sling jokes and shed clothes during burlesque parodies of Batman and Star Wars

50% Off Arts and Antiques Expo

Navy Pier

$20 $10

Visitors to the expo can browse everything from leather-bound books to diamond jewelry and 19th-century antiques

Paint a Portrait with a Professional Artist

Chicago

$50 $50

Artist Kristie Keenon teaches you how to observe, draw, and paint a portrait subject, with all materials provided—you just bring the wine

50% Pub Crawl or Brunch Tour

The Loop

$80 $40

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Groups roam the pedway's watering holes while hearing about prohibition days, or combine history with brunch

Up to 44% Off Loop Interior Architecture Tour for Two

The Loop

$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

50% Off "Fifty Shades of Grey" Parody

The Apartment

$86 $43

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Performers romp through the funny side of the hit erotic novel to the tune of Madonna, Lady Gaga, and Carly Rae Jepsen

Up to 50% Off Absolutely Chicago Segway Tours

Chicago

$50 $30

Ride up to some of Chicago's most iconic landmarks as the sun sets and the skyline begins to glow

Up to 50% Off an Inside Chicago Grand Tour

The Loop

$45 $25

A bus ferries visitors to the North and South Sides, showing them major parks, the Museum Campus, and the sights along Lake Shore Drive