Chicago Travel Guide

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Reflection of downtown Chicago, Illinois, from the Bean in Millennium Park
The "Bean" in Chicago's Millennium Park (courtesy, Chicago Convention and Tourism Bureau)

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Chicago Travel Tips

  • Take a walking tour to see some of the city's prized public art from modern masters: Marc Chagall created the rectangular mosaic in First National Plaza; a Pablo Picasso sculpture sits on Daley Plaza; and Alexander Calder's arcing red flamingo watches over an outdoor café on Dearborn Street.
  • Walk, bike, or jog on the 20-mile-long Lakefront Path connecting downtown to Navy Pier. It skirts the edge of Lake Michigan and is a favorite of city dwellers.
  • Try and get tickets to tapings of The Oprah Winfrey Show by calling 312-591-9222, but know that there's no set schedule for when the show tapes and that demand far exceeds supply.
  • Laugh out loud at The Second City on North Wells Street. It's the home of the famed comedy troupe that gave rise to SNL superstars from Dan Aykroyd to Tina Fey. (The Billy Goat Tavern on Michigan Avenue's lower level was the inspiration for John Belushi's famous "Cheezeborger!" skit, and still offers marginal food and rude employees.)
  • Stroll the tree-lined streets of Oak Park. It's the first suburb west of the city, the birthplace of Ernest Hemingway, and the one-time home of Frank Lloyd Wright.

Chicago Travel Guide

Like any great city, Chicago's got something for everyone, whether your tastes run toward world-famous museums and blow-your-budget luxury hotels or family-friendly lodgings and low-key neighborhood restaurants. Narrowing down your choices may seem daunting, but never fear: Here's your cheat sheet to the very best of the city, the places to which I send out-of-town friends and relatives when they want to experience the "real" Chicago. Some are well-known tourist attractions, others are insider secrets, but all are places and experiences that truly sum up this town. Happy exploring! Read More

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44 Questions | 42 Answers
  • Taking daughter to Chicago for her 22nd birthday week after Christmas. Ideas? Shopping other than Miracle Mile? Jazz clubs easy to walk to? Any help!
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  • How to get from Midway to Sheraton Towers on metro?
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  • hi. im taking my girlfriend to chicago, for her 22nd birthday and i want to take her out to a nice fancy restaurant. could i get few names where i could take her. and also want to take her out dancing. where could i find one of the best clubs
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Hotels

from: $130

Sofitel Chicago Water Tower

20 East Chestnut St. - Downtown
Chicago, IL 60611 Map

Distance: 2.5 mi.
(from destination center)

Hotel Class: 4 class stars

Expert Rated & Recommended
4.0
4.0
from: $116

Hilton Chicago

720 South Michigan Avenue
Chicago, IL 60605 Map

Distance: 2.1 mi.
(from destination center)

Hotel Class: 4 class stars

Expert Rated & Recommended
4.0
from: $119

Hotel Allegro Chicago

171 West Randolph Street
Chicago, IL 60601 Map

Distance: 2.5 mi.
(from destination center)

Hotel Class: 4 class stars

Expert Rated & Recommended
4.0

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Attractions

Oprah Winfrey Show (The)

Harpo Studios: 1058 West Washington St. at the corner of Carpenter and Washington
110 North Carpenter St.
Chicago, Illinois 60607

Distance: 2.3 mi. (from destination center)

Description: The Oprah Winfrey Show first aired in 1984 as AM Chicago, and eventually became the... Read More
Expert Rated & Recommended
5_0
5_0

Lakeshore Athletic Club - Illinois Center

211 North Stetson
Chicago, Illinois 60601

Distance: 2.9 mi. (from destination center)
Expert Rated & Recommended
4_0
4_0

Channing's Day Spa

54 E. Oak St.
Chicago, Illinois 60611

Distance: 3.7 mi. (from destination center)

Description: Chicago's glamour girls have softened their heels and lacquered their fingernails at Channing's for... Read More
Expert Rated & Recommended
4_0
4_0

Airports

Major Airports near Chicago

Distance (mi.)
Chicago Midway Airport 6.9 map
Chicago O'Hare International Airport 14.6 map
Milwaukee General Mitchell Airport 77.2 map

Other Smaller Airports near Chicago

Distance (mi.)
Chicago Pal-Waukee Airport 22.4 map
South Bend Regional Airport 69.5 map
Greater Rockford Airport 78.3 map

Feature Articles


Trip Ideas



GORPtravel Adventure Trips & Guided Tours

  • Route 66
    Intrepid Travel
    from $1614, 14 days
    Get your kicks on this Overland Adventure down Route 66, the infamous highway linking LA and Chicago. Road-trip down the interstates through the...



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