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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$169 Chicago, Illinois $169 & Up: Hilton Chicago O'Hare Airport 4-Star Hotel in Chicago
Expedia
$112+ Chicago, Illinois 4.5 Star Luxury Chicago Hotel on Sale! Starting from $112/nt
Jetsetter
$219 Chicago, Illinois $219 & Up: Comfort Suites Michigan Avenue 3-Star Hotel in Chicago
Expedia
$265 Chicago, Illinois American Airlines US Flight Deals
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$229 Chicago, Illinois $229 & Up: Residence Inn Chicago Downtown 3-Star Hotel in Chicago
Expedia
$291 Chicago, Illinois American Airlines US Flight Deals
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$260 Chicago, Illinois $260 & Up: Monaco Chicago - a Kimpton 4-Star Hotel in Chicago
Expedia
$273 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$282 Chicago, Illinois $282 & Up: Sofitel Chicago Water Tower 4.5-Star Hotel in Chicago
Expedia
$227 Chicago, Illinois American Airlines US Flight Deals
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$1,500 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $1,500
Expedia
$277 Chicago, Illinois American Airlines US Flight Deals
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$134 Chicago, Illinois BEST WESTERN Grant Park in Sep: $134 & Up
Save with Expedia, $33/night less
$253 Chicago, Illinois American Airlines US Flight Deals
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$104 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $104+/Nt
Expedia
$197 Chicago, Illinois American Airlines US Flight Deals
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$133 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $133+/Nt
Expedia
$155 Chicago, Illinois Cheap Flights from Boston
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$141 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $141+/Nt
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$112 Chicago, Illinois Cheap Flights from Denver
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$174 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $174+/Nt
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$173 Chicago, Illinois Cheap Flights from Houston
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$209 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $209+/Nt
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$251 Chicago, Illinois Cheap Flights from Los Angeles
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$229 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $229+/Nt
Save with Expedia, $40/night less
$328 Chicago, Illinois Cheap Flights from Miami
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$236 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $236+/Nt
Expedia
$95 Chicago, Illinois Cheap Flights from Minneapolis
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$187 Chicago, Illinois Book 3-Star BEST WESTERN River North in Chicago Fr $187+/Nt
Expedia
$195 Chicago, Illinois Cheap Flights from New York
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$213 Chicago, Illinois Book 3-Star Hampton Majestic Chicago Theatre District Fr $213+/Nt
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$226 Chicago, Illinois Cheap Flights from Newark
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$154 Chicago, Illinois Book 3.5-Star Club Quarters Chicago - Central Loop Fr $154+/Nt
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$255 Chicago, Illinois Cheap Flights from Portland
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$130 Chicago, Illinois Book 3.5-Star Indigo Chicago Downtown Gold Coast Fr $130+/Nt
Expedia
$227 Chicago, Illinois Cheap Flights from Raleigh
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$192 Chicago, Illinois Book 4-Star The Whitehall Fr $192+/Nt
Save with Expedia, $47/night less
$142 Chicago, Illinois Cheap Flights from Salt Lake City
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$169 Chicago, Illinois Book in Chicago: Save at the Central Loop in Sep Fr $169+/Nt
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$265 Chicago, Illinois Cheap Flights from San Francisco
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$209 Chicago, Illinois Book in Chicago: Save this Sep Fr $209+/Nt
Expedia
$251 Chicago, Illinois Cheap Flights from Seattle
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$212 Chicago, Illinois Book in Chicago: Save this Sep Fr $212+/Nt
Save with Expedia, $11/night less
$187 Chicago, Illinois Cheap Flights from St. Louis
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$249 Chicago, Illinois Book in Chicago: Save this Sep Fr $249+/Nt
Expedia
$125+ Chicago, Illinois Chicago on Sale! Starting From $125/nt
Jetsetter
$421 Chicago, Illinois Book in Chicago: Save this Sep Fr $421+/Nt
Save with Expedia, $105/night less
$94 Chicago, Illinois Delta US Flights on Sale
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$196 Chicago, Illinois Book the Holiday Inn Express Cass 3 Nts in Sep Fr $196+/Nt
Expedia
$122 Chicago, Illinois Delta US Flights on Sale
DealBase.com
$276 Chicago, Illinois Book the The Blackstone A Renaissance 3 Nts in Sep Fr $276+/Nt
Expedia
$522 Chicago, Illinois Great Rates in Chicago + Breakfast!
DealBase.com
$1,364 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $1,364
Expedia
$99+ Chicago, Illinois Save Up To 25% on 4-Star Chicago Hotels
trivago
$661 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $661
Expedia
$109 Chicago, Illinois Southwest Airlines Nationwide Sale
DealBase.com
$696 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $696
Expedia
$150 Chicago, Illinois Southwest Airlines Nationwide Sale
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$699 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $699
Expedia
$128 Chicago, Illinois Southwest Airlines Nationwide Sale
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$254 Chicago, Illinois Chicago Downtown, Autograph Collection in Sep: $254 & Up
Expedia
$181 Chicago, Illinois United Airlines US Fare Sale
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$203 Chicago, Illinois Chicago Savings! Book 3 Nts in Sep Fr $203+/Nt
Save with Expedia, $36/night less
$219 Chicago, Illinois Chicago Savings! Book 3 Nts in Sep Fr $219+/Nt
Expedia
$259 Chicago, Illinois Chicago Savings! Book 3 Nts in Sep Fr $259+/Nt
Expedia
$138 Chicago, Illinois Chicago Savings! Book at Chicago South Loop Fr $138+/Nt
Save with Expedia, $25/night less
$153 Chicago, Illinois Chicago Savings! Book at Chicago's Essex Inn Fr $153+/Nt
Save with Expedia, $26/night less
$295 Chicago, Illinois Chicago Savings! Book at Conrad Chicago Fr $295+/Nt
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$147 Chicago, Illinois Chicago Savings! Book at Days Inn Chicago Fr $147+/Nt
Expedia
$163 Chicago, Illinois Chicago Savings! Book at Holiday Inn Chicago Downtown Fr $163+/Nt
Expedia
$236 Chicago, Illinois Chicago Savings! Book at InterContinental Chicago Fr $236+/Nt
Expedia
$243 Chicago, Illinois Chicago Savings! Book at MileNorth, A Chicago Fr $243+/Nt
Expedia
$237 Chicago, Illinois Chicago Savings! Book at Sheraton Chicago and Towers Fr $237+/Nt
Expedia
$169 Chicago, Illinois Chicago Savings! Book at The Palmer House Hilton Fr $169+/Nt
Expedia
$483 Chicago, Illinois Chicago Savings! Book at The Peninsula Chicago Fr $483+/Nt
Expedia
$206 Chicago, Illinois Chicago Savings! Book at The Silversmith Fr $206+/Nt
Save with Expedia, $37/night less
$136 Chicago, Illinois Chicago Savings! Book at Travelodge Chicago Downtown Fr $136+/Nt
Expedia
$191 Chicago, Illinois Crowne Plaza Chicago - The Metro in Sep: $191 & Up
Expedia
$189 Chicago, Illinois Embassy Suites Chicago Downtown Lakefront in Sep: $189 & Up
Expedia
$392 Chicago, Illinois Four Seasons Chicago on Sale: Book 3 Nts in Sep Fr $392+/Nt
Save with Expedia, $43/night less
$179 Chicago, Illinois Hampton Inn & Suites Chicago - Downtown in Sep: $179 & Up
Expedia
$213 Chicago, Illinois Holiday Inn Chicago Mart Plaza River North in Sep: $213 & Up
Expedia
$190 Chicago, Illinois Holiday Inn Express Chicago-Midway Airport in Sep: $190 & Up
Expedia
$239 Chicago, Illinois Radisson Blu Aqua on Sale: Book 3 Nts in Sep Fr $239+/Nt
Expedia
$142 Chicago, Illinois Red Roof Inn Chicago Downtown Magnificent Mile in Sep: $142 & Up
Save with Expedia, $35/night less
$224 Chicago, Illinois Residence Inn Chicago Downtown / River North in Sep: $224 & Up
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$149 Chicago, Illinois River in Sep: $149 & Up
Save with Expedia, $10/night less
$604 Chicago, Illinois Save at 3.5-Star Hotel: 3 Nts + Air to Chicago Fr $604
Expedia
$2,415 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $2,415
Expedia
$592 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $592
Expedia
$779 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $779
Expedia
$812 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $812
Expedia
$241 Chicago, Illinois Save at 4-Star Raffaello: $241 & Up in Sep
Save with Expedia, $130/night less
$208 Chicago, Illinois Save at 4.5-Star Omni Chicago: $208 & Up in Sep
Save with Expedia, $51/night less
$233 Chicago, Illinois Save Big This Sep! Book 3 Nts at Kinzie Fr $233+/Nt
Expedia
$189 Chicago, Illinois Save Big This Sep! Book 3 Nts in Chicago Fr $189+/Nt
Expedia
$203 Chicago, Illinois Save Big This Sep! Book 3 Nts in Chicago Fr $203+/Nt
Expedia
$237 Chicago, Illinois Save Big This Sep! Book 3 Nts in Chicago Fr $237+/Nt
Expedia
$179 Chicago, Illinois Save in Chicago: Book 3 Nts in Sep Fr $179+/Nt
Expedia
$183 Chicago, Illinois Save in Chicago: Book 3 Nts in Sep Fr $183+/Nt
Expedia
PRICEDESTINATIONDEAL
$145 New York City, New York Cheap Flights from Washington, DC
DealBase.com
$323 New York City, New York Cheap Flights from San Diego
DealBase.com
$196 New York City, New York Cheap Flights from Tampa
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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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