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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$120 Chicago, Illinois $120 & Up: River 3.5-Star Hotel in Chicago
Save with Expedia, $13/night less
$268 Chicago, Illinois American Airlines Domestic Getaways for This Weekend - 3/6/15
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$146 Chicago, Illinois $146 & Up: Raffaello 4-Star Hotel in Chicago
Save with Expedia, $40/night less
$280 Chicago, Illinois American Airlines Domestic Getaways for This Weekend - 3/6/15
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$322 Chicago, Illinois $322 & Up: Waldorf Astoria Chicago 5-Star Hotel in Chicago
Expedia
$9 Chicago, Illinois Cheap Car Rentals in Chicago Fr $9/Day
CarRentals.com
$557 Chicago, Illinois 3.5-Star Chicago Sale! 3 Nts + Air Fr $557
Expedia
$38+ Chicago, Illinois Dolands Addition Vacation Rental Deals From $38
Tripping
$1,041 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $1,041
Expedia
$142+ Chicago, Illinois Experience Chicago! Book Cheap Flights From $142 R/T
Fare Buzz
$196 Chicago, Illinois Book 3 Nts in Chicago this Mar Fr $196+/Nt
Expedia
$49 Chicago, Illinois Frontier Airlines Chicago Sale
DealBase.com
$219 Chicago, Illinois Book 3 Nts in Chicago this Mar Fr $219+/Nt
Expedia
$69 Chicago, Illinois Frontier Airlines Chicago Sale
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$144 Chicago, Illinois Book 3-Star BEST WESTERN River North in Chicago Fr $144+/Nt
Expedia
$23 Chicago, Illinois Spirit Airlines $9 Fare Club Deals
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$149 Chicago, Illinois Book 3-Star Comfort Suites Michigan Avenue Fr $149+/Nt
Expedia
$23 Chicago, Illinois Spirit Airlines $9 Fare Club Deals
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$133 Chicago, Illinois Book 3-Star Hampton Majestic Chicago Theatre District Fr $133+/Nt
Expedia
$23 Chicago, Illinois Spirit Airlines $9 Fare Club Deals
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$230 Chicago, Illinois Book 3-Star Holiday Inn Chicago - Midway Airport Fr $230+/Nt
Expedia
$43 Chicago, Illinois Spirit Airlines $9 Fare Club Deals
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$133 Chicago, Illinois Book 3.5-Star Crowne Plaza Chicago - The Metro Fr $133+/Nt
Expedia
$63 Chicago, Illinois Spirit Airlines $9 Fare Club Deals
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$123 Chicago, Illinois Book 3.5-Star Embassy Suites Chicago Downtown Fr $123+/Nt
Expedia
$23 Chicago, Illinois Spirit Airlines $9 Fare Club Deals
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$125 Chicago, Illinois Book 3.5-Star Kinzie in Chicago Fr $125+/Nt
Save with Expedia, $31/night less
$23 Chicago, Illinois Spirit Airlines $9 Fare Club Deals
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$193 Chicago, Illinois Book 3.5-Star Renaissance Chicago O'Hare Suites Fr $193+/Nt
Expedia
$23 Chicago, Illinois Spirit Airlines $9 Fare Club Deals
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$130 Chicago, Illinois Book 3.5-Star Wyndham Grand Chicago Riverfront Fr $130+/Nt
Save with Expedia, $23/night less
$78 Chicago, Illinois Spirit Airlines $9 Fare Club Deals
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$109 Chicago, Illinois Book 4-Star Hilton Chicago O'Hare Airport in Chicago Fr $109+/Nt
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$63 Chicago, Illinois Spirit Airlines $9 Fare Club Deals
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$142 Chicago, Illinois Book 4-Star Hyatt Chicago Magnificent Mile in Chicago Fr $142+/Nt
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$63 Chicago, Illinois Spirit Airlines $9 Fare Club Deals
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$205 Chicago, Illinois Book 4-Star The Westin Chicago River North Fr $205+/Nt
Expedia
$38 Chicago, Illinois Spirit Airlines $9 Fare Club Deals
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$128 Chicago, Illinois Book 4-Star The Westin Michigan Avenue Chicago Fr $128+/Nt
Expedia
$93 Chicago, Illinois Spirit Airlines $9 Fare Club Deals
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$123 Chicago, Illinois Book 4-Star The Whitehall in Chicago Fr $123+/Nt
Save with Expedia, $26/night less
$63 Chicago, Illinois Spirit Airlines $9 Fare Club Deals
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$135 Chicago, Illinois Book 4.5-Star InterContinental Chicago Fr $135+/Nt
Expedia
$53 Chicago, Illinois Spirit Airlines $9 Fare Club Deals
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$150 Chicago, Illinois Book 4.5-Star The James Chicago Fr $150+/Nt
Save with Expedia, $26/night less
$83 Chicago, Illinois Spirit Airlines $9 Fare Club Deals
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$104 Chicago, Illinois Book in Chicago: Save this Mar Fr $104+/Nt
Expedia
$23 Chicago, Illinois Spirit Airlines $9 Fare Club Deals
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$178 Chicago, Illinois Book in Chicago: Save this Mar Fr $178+/Nt
Expedia
$276 Chicago, Illinois United Airlines Weekend Specials for 3/6/15
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$69 Chicago, Illinois Book in Chicago: Save this Mar Fr $69+/Nt
Save with Expedia, $26/night less
$328 Chicago, Illinois United Airlines Weekend Specials for 3/6/15
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$159 Chicago, Illinois Book the Burnham - a Kimpton 3 Nts in Mar Fr $159+/Nt
Expedia
$228 Chicago, Illinois United Airlines Weekend Specials for 3/6/15
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$104 Chicago, Illinois Book the Holiday Inn Chicago O'Hare 3 Nts in Mar Fr $104+/Nt
Expedia
$180 Chicago, Illinois Virgin America Great Deals Across the US
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$135 Chicago, Illinois Book the Sheraton Chicago and Towers 3 Nts in Mar Fr $135+/Nt
Expedia
$184 Chicago, Illinois Virgin America Great Deals Across the US
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$1,660 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $1,660
Expedia
$200 Chicago, Illinois Virgin America Great Deals Across the US
DealBase.com
$1,928 Chicago, Illinois Chicago 4.5-Star Hotel Sale! 3 Nts + Air Fr $1,928
Expedia
$200 Chicago, Illinois Virgin America Great Deals Across the US
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$122 Chicago, Illinois Chicago Downtown, Autograph Collection in Mar: $122 & Up
Expedia
$200 Chicago, Illinois Virgin America Great Deals Across the US
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$117 Chicago, Illinois Chicago Savings! Book 3 Nts in Mar at Blake Chicago Fr $117+/Nt
Expedia
$153 Chicago, Illinois Chicago Savings! Book 3 Nts in Mar Fr $153+/Nt
Expedia
$156 Chicago, Illinois Chicago Savings! Book 3 Nts in Mar Fr $156+/Nt
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$159 Chicago, Illinois Chicago Savings! Book 3 Nts in Mar Fr $159+/Nt
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$244 Chicago, Illinois Chicago Savings! Book 3 Nts in Mar Fr $244+/Nt
Save with Expedia, $121/night less
$250 Chicago, Illinois Chicago Savings! Book 3 Nts in Mar Fr $250+/Nt
Save with Expedia, $125/night less
$259 Chicago, Illinois Chicago Savings! Book 3 Nts in Mar Fr $259+/Nt
Save with Expedia, $86/night less
$88 Chicago, Illinois Chicago Savings! Book 3 Nts in Mar Fr $88+/Nt
Expedia
$144 Chicago, Illinois Chicago Savings! Book at BEST WESTERN Grant Park Fr $144+/Nt
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$130 Chicago, Illinois Chicago Savings! Book at Buckingham Athletic Club Fr $130+/Nt
Save with Expedia, $9/night less
$109 Chicago, Illinois Chicago Savings! Book at Central Loop Fr $109+/Nt
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$186 Chicago, Illinois Chicago Savings! Book at JW Marriott Chicago Fr $186+/Nt
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$252 Chicago, Illinois Chicago Savings! Book at Park Hyatt Chicago Fr $252+/Nt
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$151 Chicago, Illinois Chicago Savings! Book at Radisson Blu Aqua Fr $151+/Nt
Expedia
$156 Chicago, Illinois Chicago Savings! Book at Renaissance Chicago Fr $156+/Nt
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$172 Chicago, Illinois Chicago Savings! Book at Sofitel Chicago Water Tower Fr $172+/Nt
Expedia
$171 Chicago, Illinois Chicago Savings! Book at Swissotel Chicago Fr $171+/Nt
Save with Expedia, $19/night less
$136 Chicago, Illinois Chicago Savings! Book at The Palmer House Hilton Fr $136+/Nt
Expedia
$120 Chicago, Illinois Chicago Savings! Book at W Chicago Lakeshore Fr $120+/Nt
Expedia
$109 Chicago, Illinois Chicago South Loop in Mar: $109 & Up
Expedia
$90 Chicago, Illinois Club Quarters Chicago - Central Loop in Mar: $90 & Up
Save with Expedia, $9/night less
$174 Chicago, Illinois Courtyard Chicago Downtown/Magnificent Mile in Mar: $174 & Up
Expedia
$146 Chicago, Illinois Crowne Plaza Chicago Magnificent Mile in Mar: $146 & Up
Expedia
$139 Chicago, Illinois Hampton Inn & Suites Chicago - Downtown in Mar: $139 & Up
Expedia
$257 Chicago, Illinois Holiday Inn Express Chicago-Midway Airport in Mar: $257 & Up
Expedia
$159 Chicago, Illinois Homewood Suites by Hilton Chicago Downtown in Mar: $159 & Up
Expedia
$163 Chicago, Illinois Mar deal: Chicago Marriott Downtown Magnificent Mile Fr $163+/Nt
Expedia
$103 Chicago, Illinois Mar deal: Hostelling International Chicago Fr $103+/Nt
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$159 Chicago, Illinois Mar deal: The Drake Fr $159+/Nt
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$173 Chicago, Illinois Mar deal: theWit - A DoubleTree by Hilton Fr $173+/Nt
Expedia
$162 Chicago, Illinois Omni Chicago in Mar: $162 & Up
Save with Expedia, $17/night less
$121 Chicago, Illinois PUBLIC Chicago in Mar: $121 & Up
Save with Expedia, $65/night less
$82 Chicago, Illinois Red Roof Inn Chicago Downtown Magnificent Mile in Mar: $82 & Up
Expedia
$138 Chicago, Illinois Save at 3.5-Star The Silversmith: $138 & Up in Mar
Save with Expedia, $15/night less
$701 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $701
Expedia
$164 Chicago, Illinois Save at 4-Star The Blackstone A Renaissance: $164 & Up in Mar
Expedia
PRICEDESTINATIONDEAL
$43 Philadelphia, Pennsylvania Spirit Airlines $9 Fare Club Deals
DealBase.com
$23 Philadelphia, Pennsylvania Spirit Airlines $9 Fare Club Deals
DealBase.com
$270 Philadelphia, Pennsylvania US Airways Domestic e-Saver Specials for 3/7/15
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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