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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$119 Chicago, Illinois $119 & Up: Comfort Suites Michigan Avenue 3-Star Hotel in Chicago
Expedia
$85+ Chicago, Illinois 4-Star Chicago Hotels from $85
trivago
$144 Chicago, Illinois $144 & Up: The Silversmith 3.5-Star Hotel in Chicago
Save with Expedia, $25/night less
$112+ Chicago, Illinois 4.5 Star Luxury Chicago Hotel on Sale! Starting from $112/nt
Jetsetter
$264 Chicago, Illinois $264 & Up: Four Seasons Chicago 5-Star Hotel in Chicago
Save with Expedia, $131/night less
$310 Chicago, Illinois American Airlines Domestic Getaways for This Weekend - 10/31/14
DealBase.com
$341 Chicago, Illinois 3.5-Star Chicago Sale! 3 Nts + Air Fr $341
Expedia
$280 Chicago, Illinois American Airlines Domestic Getaways for This Weekend - 10/31/14
DealBase.com
$1,354 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $1,354
Expedia
$268 Chicago, Illinois American Airlines Domestic Getaways for This Weekend - 10/31/14
DealBase.com
$85 Chicago, Illinois ACME Company Chicago on Sale: Book 3 Nts in Oct Fr $85+/Nt
Save with Expedia, $14/night less
$280 Chicago, Illinois American Airlines Domestic Getaways for This Weekend - 10/31/14
DealBase.com
$72 Chicago, Illinois BEST WESTERN Grant Park in Oct: $72 & Up
Save with Expedia, $18/night less
$197 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$90 Chicago, Illinois BEST WESTERN River North on Sale: Book 3 Nts in Oct Fr $90+/Nt
Expedia
$253 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$249 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $249+/Nt
Expedia
$245 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$74 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $74+/Nt
Expedia
$13 Chicago, Illinois Cheap Car Rentals in Chicago Fr $13/Day
CarRentals.com
$85 Chicago, Illinois Book 3-Star Hampton Inn & Suites Chicago - Downtown Fr $85+/Nt
Expedia
$17 Chicago, Illinois Cheap Car Rentals in Chicago Fr $17/Day
CarRentals.com
$143 Chicago, Illinois Book 3-Star Hampton Majestic Chicago Theatre District Fr $143+/Nt
Expedia
$125+ Chicago, Illinois Chicago on Sale! Starting From $125/nt
Jetsetter
$99 Chicago, Illinois Book 3.5-Star Blake Chicago in Chicago Fr $99+/Nt
Expedia
$162 Chicago, Illinois Southwest Airlines Grab Your Favorite Seat Sale
DealBase.com
$81 Chicago, Illinois Book 3.5-Star Club Quarters Chicago - Central Loop Fr $81+/Nt
Save with Expedia, $8/night less
$115 Chicago, Illinois Southwest Airlines Grab Your Favorite Seat Sale
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$119 Chicago, Illinois Book 3.5-Star Crowne Plaza Chicago - The Metro Fr $119+/Nt
Save with Expedia, $7/night less
$134 Chicago, Illinois Southwest Airlines Grab Your Favorite Seat Sale
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$111 Chicago, Illinois Book 3.5-Star Indigo Chicago Downtown Gold Coast Fr $111+/Nt
Expedia
$169 Chicago, Illinois Southwest Airlines Grab Your Favorite Seat Sale
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$96 Chicago, Illinois Book 3.5-Star River Fr $96+/Nt
Save with Expedia, $10/night less
$134 Chicago, Illinois Southwest Airlines Grab Your Favorite Seat Sale
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$139 Chicago, Illinois Book 4-Star Hilton Chicago O'Hare Airport in Chicago Fr $139+/Nt
Expedia
$112 Chicago, Illinois Southwest Airlines Grab Your Favorite Seat Sale
DealBase.com
$100 Chicago, Illinois Book 4-Star The Westin Michigan Avenue Chicago Fr $100+/Nt
Expedia
$53 Chicago, Illinois Spirit Airlines New Orleans Non-Stop Specials
DealBase.com
$151 Chicago, Illinois Book 4.5-Star Sofitel Chicago Water Tower in Chicago Fr $151+/Nt
Expedia
$133 Chicago, Illinois United Airlines US Fare Sale
DealBase.com
$297 Chicago, Illinois Book 5-Star Trump International & Tower Chicago Fr $297+/Nt
Save with Expedia, $98/night less
$328 Chicago, Illinois United Airlines Weekend Specials for 10/31/14
DealBase.com
$103 Chicago, Illinois Book in Chicago: Save this Oct Fr $103+/Nt
Expedia
$278 Chicago, Illinois United Airlines Weekend Specials for 10/31/14
DealBase.com
$128 Chicago, Illinois Book in Chicago: Save this Oct Fr $128+/Nt
Save with Expedia, $32/night less
$228 Chicago, Illinois United Airlines Weekend Specials for 10/31/14
DealBase.com
$139 Chicago, Illinois Book in Chicago: Save this Oct Fr $139+/Nt
Save with Expedia, $25/night less
$270 Chicago, Illinois US Airways Domestic e-Saver Specials for 11/1/14
DealBase.com
$85 Chicago, Illinois Book in Chicago: Save this Oct Fr $85+/Nt
Save with Expedia, $14/night less
$95 Chicago, Illinois Book in Chicago: Save this Oct Fr $95+/Nt
Expedia
$159 Chicago, Illinois Book the Renaissance Chicago 3 Nts in Oct Fr $159+/Nt
Expedia
$143 Chicago, Illinois Book the Residence Inn Chicago Downtown 3 Nts in Oct Fr $143+/Nt
Expedia
$130 Chicago, Illinois Book the W Chicago Lakeshore 3 Nts in Oct Fr $130+/Nt
Expedia
$1,230 Chicago, Illinois Chicago 3.5-Star Hotel Sale! 3 Nts + Air Fr $1,230
Expedia
$706 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $706
Expedia
$161 Chicago, Illinois Chicago Marriott at Medical District/UIC in Oct: $161 & Up
Expedia
$109 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct at Central Loop Fr $109+/Nt
Expedia
$110 Chicago, Illinois Chicago Savings! Book at Burnham - a Kimpton Fr $110+/Nt
Save with Expedia, $19/night less
$110 Chicago, Illinois Chicago Savings! Book at Hard Rock Chicago Fr $110+/Nt
Save with Expedia, $19/night less
$102 Chicago, Illinois Chicago Savings! Book at InterContinental Chicago Fr $102+/Nt
Expedia
$140 Chicago, Illinois Chicago Savings! Book at Monaco Chicago - a Kimpton Fr $140+/Nt
Save with Expedia, $59/night less
$128 Chicago, Illinois Chicago Savings! Book at Omni Chicago Fr $128+/Nt
Save with Expedia, $31/night less
$147 Chicago, Illinois Chicago Savings! Book at Palomar Chicago, a Kimpton Fr $147+/Nt
Save with Expedia, $26/night less
$129 Chicago, Illinois Chicago Savings! Book at Sheraton Chicago and Towers Fr $129+/Nt
Expedia
$134 Chicago, Illinois Chicago Savings! Book at The Blackstone A Renaissance Fr $134+/Nt
Expedia
$89 Chicago, Illinois Chicago Savings! Book at The Palmer House Hilton Fr $89+/Nt
Expedia
$350 Chicago, Illinois Chicago Savings! Book at The Peninsula Chicago Fr $350+/Nt
Save with Expedia, $175/night less
$218 Chicago, Illinois Chicago Savings! Book at W Chicago - City Center Fr $218+/Nt
Expedia
$351 Chicago, Illinois Chicago Savings! Book at Waldorf Astoria Chicago Fr $351+/Nt
Expedia
$102 Chicago, Illinois Holiday Inn Chicago Downtown in Oct: $102 & Up
Expedia
$140 Chicago, Illinois La Quinta Inn & Suites Chicago Downtown in Oct: $140 & Up
Expedia
$85 Chicago, Illinois Oct deal: Crowne Plaza Chicago Magnificent Mile Fr $85+/Nt
Expedia
$136 Chicago, Illinois Oct deal: dana and spa Fr $136+/Nt
Expedia
$95 Chicago, Illinois Oct deal: Homewood Suites by Hilton Chicago Downtown Fr $95+/Nt
Expedia
$97 Chicago, Illinois Oct deal: Hyatt Chicago Magnificent Mile Fr $97+/Nt
Expedia
$94 Chicago, Illinois Oct deal: Hyatt Regency Chicago Fr $94+/Nt
Expedia
$149 Chicago, Illinois Oct deal: Kinzie Fr $149+/Nt
Expedia
$112 Chicago, Illinois Oct deal: Radisson Blu Aqua Fr $112+/Nt
Expedia
$203 Chicago, Illinois Oct deal: The Westin Chicago River North Fr $203+/Nt
Expedia
$115 Chicago, Illinois Oct deal: theWit - A DoubleTree by Hilton Fr $115+/Nt
Expedia
$68 Chicago, Illinois Red Roof Inn Chicago Downtown Magnificent Mile in Oct: $68 & Up
Save with Expedia, $17/night less
$123 Chicago, Illinois Save at 3.5-Star Buckingham Athletic Club: $123 & Up in Oct
Expedia
$159 Chicago, Illinois Save at 4.5-Star Conrad Chicago: $159 & Up in Oct
Expedia
$260 Chicago, Illinois Save at 5-Star Park Hyatt Chicago: $260 & Up in Oct
Expedia
$99 Chicago, Illinois Save Big This Oct! Book 3 Nts at Chicago South Loop Fr $99+/Nt
Expedia
$104 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $104+/Nt
Expedia
$108 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $108+/Nt
Save with Expedia, $58/night less
$109 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $109+/Nt
Expedia
$119 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $119+/Nt
Expedia
$126 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $126+/Nt
Expedia
$127 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $127+/Nt
Expedia
$128 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $128+/Nt
Expedia
$136 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $136+/Nt
Expedia
$144 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $144+/Nt
Save with Expedia, $15/night less
$86 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $86+/Nt
Expedia
$89 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $89+/Nt
Expedia
$93 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $93+/Nt
Expedia
$108 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $108+/Nt
Save with Expedia, $57/night less
$140 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $140+/Nt
Expedia
$153 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $153+/Nt
Save with Expedia, $26/night less
PRICEDESTINATIONDEAL
$118 New York City, New York Cheap Flights from Washington, DC
DealBase.com
$197 New York City, New York Cheap Flights from Detroit
DealBase.com
$205 New York City, New York Cheap Flights from Denver
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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