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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$59 Chicago, Illinois Frontier Airlines Little Fares from Big Cities Promotion
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$100+ Chicago, Illinois $100: Chicago Lake Shore Hotel
Priceline.com
$149 Chicago, Illinois $149 & Up: Hilton Chicago 4-Star Hotel in Chicago
Expedia
$101+ Chicago, Illinois $101: Millennium Knickerbocker, Chicago
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$186 Chicago, Illinois $186 & Up: Burnham - a Kimpton 4-Star Hotel in Chicago
Expedia
$103+ Chicago, Illinois $103: The Buckingham Athletic Club & Hotel, Chicago
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$249 Chicago, Illinois $249 & Up: Swissotel Chicago 4-Star Hotel in Chicago
Save with Expedia, $27/night less
$105+ Chicago, Illinois $105: The Palmer House Hilton, Chicago
Priceline.com
$1,008 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $1,008
Expedia
$109+ Chicago, Illinois $109: SpringHill Suites Chicago O'Hare by Marriott
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$589 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $589
Expedia
$111+ Chicago, Illinois $111: Chicago's Essex Inn
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$647 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $647
Expedia
$119+ Chicago, Illinois $119: The Palmer House Hilton, Chicago
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$723 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $723
Expedia
$123+ Chicago, Illinois $123: Radisson Blu Aqua Hotel Chicago
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$749 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $749
Expedia
$134+ Chicago, Illinois $134: Congress Plaza Hotel, Chicago
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$750 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $750
Expedia
$135+ Chicago, Illinois $135: The Westin Chicago River North
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$118+ Chicago, Illinois Air Fare Sale! Atlanta to Chicago From $118 R/T*
FareBuzz
$138+ Chicago, Illinois $138: dana hotel and spa, Chicago
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$230 Chicago, Illinois American Airlines Domestic Getaways for This Weekend - 7/31/15
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$139+ Chicago, Illinois $139: Wyndham Grand Chicago Riverfront
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$204 Chicago, Illinois BEST WESTERN Grant Park on Sale: Book 3 Nts in Jul Fr $204+/Nt
Expedia
$141+ Chicago, Illinois $141: Hard Rock Hotel Chicago
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$149 Chicago, Illinois Book 3 Nts in Chicago this Jul Fr $149+/Nt
Save with Expedia, $37/night less
$145+ Chicago, Illinois $145: PUBLIC Chicago
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$152 Chicago, Illinois Book 3 Nts in Chicago this Jul Fr $152+/Nt
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$147+ Chicago, Illinois $147: Hotel Palomar Chicago, a Kimpton Hotel
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$153 Chicago, Illinois Book 3 Nts in Chicago this Jul Fr $153+/Nt
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$149+ Chicago, Illinois $149: Crowne Plaza Chicago Metro
Hotels.com
$180 Chicago, Illinois Book 3 Nts in Chicago this Jul Fr $180+/Nt
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$152+ Chicago, Illinois $152: Hyatt Chicago Magnificent Mile
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$180 Chicago, Illinois Book 3 Nts in Chicago this Jul Fr $180+/Nt
Save with Expedia, $59/night less
$153+ Chicago, Illinois $153: Chicago Marriott Midway
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$199 Chicago, Illinois Book 3 Nts in Chicago this Jul Fr $199+/Nt
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$155+ Chicago, Illinois $155: Sofitel Chicago Water Tower
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$209 Chicago, Illinois Book 3 Nts in Chicago this Jul Fr $209+/Nt
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$181+ Chicago, Illinois $181: Hotel Burnham, a Kimpton Hotel, Chicago
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$320 Chicago, Illinois Book 3 Nts in Chicago this Jul Fr $320+/Nt
Save with Expedia, $160/night less
$188+ Chicago, Illinois $188: Loews Chicago Hotel
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$126 Chicago, Illinois Book 3-Star Congress Plaza Fr $126+/Nt
Save with Expedia, $13/night less
$242+ Chicago, Illinois $242: Four Seasons Hotel Chicago
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$199 Chicago, Illinois Book 3-Star Hampton Majestic Chicago Theatre District Fr $199+/Nt
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$243+ Chicago, Illinois $243: The Ritz-Carlton Chicago - A Four Seasons Hotel
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$173 Chicago, Illinois Book 3-Star La Quinta Inn & Suites Chicago Downtown Fr $173+/Nt
Expedia
$324+ Chicago, Illinois $324: The Langham Chicago
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$198 Chicago, Illinois Book 4-Star Sheraton Chicago and Towers in Chicago Fr $198+/Nt
Expedia
$395+ Chicago, Illinois $395: The Peninsula Chicago
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$179 Chicago, Illinois Book 4-Star The Westin Michigan Avenue Chicago Fr $179+/Nt
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$71+ Chicago, Illinois $71: Inn of Chicago, an Ascend Hotel Collection Member
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$192 Chicago, Illinois Book in Chicago: Save at the Omni Chicago in Jul Fr $192+/Nt
Save with Expedia, $47/night less
$88+ Chicago, Illinois $88: Embassy Suites Chicago Downtown
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$183 Chicago, Illinois Book in Chicago: Save this Jul Fr $183+/Nt
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$89+ Chicago, Illinois $89: City Suites Hotel, Chicago
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$257 Chicago, Illinois Book in Chicago: Save this Jul Fr $257+/Nt
Expedia
$92+ Chicago, Illinois $92: ACME Hotel Company Chicago
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$279 Chicago, Illinois Book in Chicago: Save this Jul Fr $279+/Nt
Expedia
$99+ Chicago, Illinois $99: Hilton Chicago O'Hare Airport
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$167+ Chicago, Illinois Book Now & Save! Dallas to Chicago From $167 R/T*
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$144 Chicago, Illinois Book the Club Quarters, Central Loop 3 Nts in Jul Fr $144+/Nt
Save with Expedia, $35/night less
$242+ Chicago, Illinois Book Now & Save! Las Vegas to Chicago From $242 R/T*
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$179 Chicago, Illinois Book the Comfort Suites Michigan Avenue 3 Nts in Jul Fr $179+/Nt
Expedia
$165+ Chicago, Illinois Book Now & Save! Washington to Chicago From $165 R/T*
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$203 Chicago, Illinois Book the The Blackstone A Renaissance 3 Nts in Jul Fr $203+/Nt
Expedia
$199+ Chicago, Illinois Cheap Air Fares! Phoenix to Chicago From $199 R/T*
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$89+ Chicago, Illinois Chicago Hotel Deals For As Low As $89/nt!
Jetsetter
$161 Chicago, Illinois Chicago Savings! Book 3 Nts in Jul Fr $161+/Nt
Expedia
$300+ Chicago, Illinois Discounted Air Fares! Portland to Chicago From $300 R/T*
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$189 Chicago, Illinois Chicago Savings! Book 3 Nts in Jul Fr $189+/Nt
Expedia
$434+ Chicago, Illinois Discover the Midwest! Seattle to Chicago From $434 R/T*
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$120 Chicago, Illinois Chicago Savings! Book at BEST WESTERN River North Fr $120+/Nt
Expedia
$168+ Chicago, Illinois Don't Pay More! Orlando to Chicago From $168 R/T*
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$136 Chicago, Illinois Chicago Savings! Book at Holiday Inn Express Cass Fr $136+/Nt
Expedia
$247+ Chicago, Illinois Enjoy Big Savings! Los Angeles to Chicago From $247 R/T*
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$349 Chicago, Illinois Chicago Savings! Book at JW Marriott Chicago Fr $349+/Nt
Expedia
$199+ Chicago, Illinois Experience Illinois! Boston to Chicago From $199 R/T*
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$172 Chicago, Illinois Chicago Savings! Book at Kinzie Fr $172+/Nt
Save with Expedia, $31/night less
$228+ Chicago, Illinois Explore the Midwest! Denver to Chicago From $228 R/T*
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$237 Chicago, Illinois Chicago Savings! Book at Radisson Blu Aqua Fr $237+/Nt
Expedia
$263+ Chicago, Illinois Explore the Midwest! San Francisco to Chicago From $263 R/T*
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$138 Chicago, Illinois Chicago Savings! Book at River Fr $138+/Nt
Save with Expedia, $21/night less
$137+ Chicago, Illinois FareBuzz Advantage! Philadelphia to Chicago From $137 R/T*
FareBuzz
$212 Chicago, Illinois Chicago Savings! Book at Sofitel Chicago Water Tower Fr $212+/Nt
Expedia
$137+ Chicago, Illinois Fly for Less! Houston to Chicago From $137 R/T*
FareBuzz
$173 Chicago, Illinois Chicago Savings! Book at The Palmer House Hilton Fr $173+/Nt
Expedia
$49 Chicago, Illinois Frontier Airlines $49 Sale
DealBase.com
$332 Chicago, Illinois Chicago Savings! Book at Waldorf Astoria Chicago Fr $332+/Nt
Expedia
$69 Chicago, Illinois Frontier Airlines Colorado Day Sale
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$259 Chicago, Illinois Conrad Chicago on Sale: Book 3 Nts in Jul Fr $259+/Nt
Expedia
$39 Chicago, Illinois Frontier Airlines Little Fares from Big Cities Promotion
DealBase.com
$163 Chicago, Illinois Courtyard Chicago Downtown River North in Jul: $163 & Up
Expedia
$99 Chicago, Illinois Frontier Airlines Little Fares from Big Cities Promotion
DealBase.com
$153 Chicago, Illinois Doubletree by Hilton Chicago Magnificent Mile in Jul: $153 & Up
Expedia
$89 Chicago, Illinois Frontier Airlines Little Fares from Big Cities Promotion
DealBase.com
$190 Chicago, Illinois Embassy Suites by Hilton Chicago Downtown in Jul: $190 & Up
Expedia
$99 Chicago, Illinois Frontier Airlines Little Fares from Big Cities Promotion
DealBase.com
$174 Chicago, Illinois Hilton Suites Chicago/Magnificent Mile in Jul: $174 & Up
Expedia
$49 Chicago, Illinois Frontier Airlines Little Fares from Big Cities Promotion
DealBase.com
PRICEDESTINATIONDEAL
$81 Philadelphia, Pennsylvania Cheap Flights from Dallas
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$314 Philadelphia, Pennsylvania Cheap Flights from San Francisco
DealBase.com
$167 Philadelphia, Pennsylvania Cheap Flights from Las Vegas
DealBase.com
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Chicago Travel Tips

A shiny metropolis where complete strangers ask you if you need directions? Only in the Midwest. Take in loads of friendliness, not to mention cool architecture and major museums.
  • It's a great view … if you're a girl. One of the best views of the city is from the ladies' room in the Hancock Building's Signature Lounge. Tough luck, gentlemen.
  • You can make your mark, just don't use profanity. Gino's East Pizza bakes pies-to-die-for and features patron-placed graffiti all over its walls and tables.
  • Fond o' fondue, are you? Us too. Visit Geja's Cafe in Lincoln Park, a romantically-lit grotto with an astounding array of dip-able dining that also features flamenco and classical guitarists.
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