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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$207 Chicago, Illinois Southwest Airlines Mexico and Caribbean Sale
DealBase.com
$167+ Chicago, Illinois Holiday in Illinois! Flights to Chicago From $167 R/T
FareBuzz
$327 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$88 Chicago, Illinois Chicago Savings! Book at MileNorth, A Chicago Fr $88+/Nt
Save with Expedia, $21/night less
$218 Chicago, Illinois Southwest Airlines Mexico and Caribbean Sale
DealBase.com
$88 Chicago, Illinois Small budget: Stay in Chicago this Jan Fr $88+/Nt
Expedia
$171 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$324 Chicago, Illinois Save in Chicago: Book 3 Nts in Jan Fr $324+/Nt
Save with Expedia, $161/night less
$133 Chicago, Illinois Southwest Airlines Touchdown for Less
DealBase.com
$152 Chicago, Illinois Save at 4-Star Palomar Chicago, a Kimpton: $152 & Up in Jan
Save with Expedia, $7/night less
$34 Chicago, Illinois Spirit Airlines Tuesday and Wednesday Sale
DealBase.com
$99 Chicago, Illinois Book 3 Nts in Chicago this Jan Fr $99+/Nt
Expedia
$167 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$130 Chicago, Illinois Save Big This Jan! Book 3 Nts in Chicago at Raffaello Fr $130+/Nt
Save with Expedia, $69/night less
$34 Chicago, Illinois Spirit Airlines Tuesday and Wednesday Sale
DealBase.com
$160 Chicago, Illinois Jan deal: The Westin Chicago River North Fr $160+/Nt
Expedia
$169 Chicago, Illinois Southwest Airlines Touchdown for Less
DealBase.com
$96 Chicago, Illinois Book 3-Star Hampton Majestic Chicago Theatre District Fr $96+/Nt
Expedia
$164 Chicago, Illinois Alaska Airlines Flight Deals
DealBase.com
$129 Chicago, Illinois Book the Sheraton Chicago and Towers 3 Nts in Jan Fr $129+/Nt
Expedia
$90 Chicago, Illinois Southwest Airlines Touchdown for Less
DealBase.com
$345 Chicago, Illinois $345 & Up: Waldorf Astoria Chicago 5-Star Hotel in Chicago
Expedia
$34 Chicago, Illinois Spirit Airlines Tuesday and Wednesday Sale
DealBase.com
$117 Chicago, Illinois $117 & Up: Kinzie 3.5-Star Hotel in Chicago
Save with Expedia, $29/night less
$179 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$119 Chicago, Illinois Book 3-Star Residence Inn Chicago Downtown Fr $119+/Nt
Expedia
$200 Chicago, Illinois Virgin America Great Deals Across the US
DealBase.com
$287 Chicago, Illinois Save at 5-Star The Peninsula Chicago: $287 & Up in Jan
Save with Expedia, $143/night less
$291 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$127 Chicago, Illinois Chicago Savings! Book 3 Nts in Jan Fr $127+/Nt
Save with Expedia, $23/night less
$188 Chicago, Illinois Southwest Airlines Touchdown for Less
DealBase.com
$126 Chicago, Illinois Small budget: Stay in Chicago this Jan Fr $126+/Nt
Expedia
$135 Chicago, Illinois United Airlines US Fare Sale
DealBase.com
$101 Chicago, Illinois Jan deal: Holiday Inn Chicago Mart Plaza River North Fr $101+/Nt
Expedia
$34 Chicago, Illinois Spirit Airlines Tuesday and Wednesday Sale
DealBase.com
$169 Chicago, Illinois Small budget: Stay in Chicago this Jan Fr $169+/Nt
Expedia
$34 Chicago, Illinois Spirit Airlines Tuesday and Wednesday Sale
DealBase.com
$122 Chicago, Illinois Special deal: 4.5-Star InterContinental Chicago Fr $122+/Nt
Expedia
$225 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$78 Chicago, Illinois Chicago Savings! Book at BEST WESTERN Grant Park Fr $78+/Nt
Expedia
$324 Chicago, Illinois Sun Country Airlines Anchorage Specials
DealBase.com
$76 Chicago, Illinois Doubletree by Hilton Chicago Magnificent Mile in Jan: $76 & Up
Expedia
$165 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$152 Chicago, Illinois Save Big This Jan! Book 3 Nts in Chicago Fr $152+/Nt
Expedia
$113 Chicago, Illinois Delta US Fare Sale
DealBase.com
$68 Chicago, Illinois Book 3 Nts in Chicago this Jan Fr $68+/Nt
Expedia
$169 Chicago, Illinois Alaska Airlines Flight Deals
DealBase.com
$119 Chicago, Illinois Book 4-Star The Palmer House Hilton Fr $119+/Nt
Expedia
$137 Chicago, Illinois Southwest Airlines Touchdown for Less
DealBase.com
$127 Chicago, Illinois Book 4-Star The Westin Michigan Avenue Chicago Fr $127+/Nt
Expedia
$169 Chicago, Illinois Virgin America Great Deals Across the US
DealBase.com
$81 Chicago, Illinois Jan deal: Homewood Suites by Hilton Chicago Downtown Fr $81+/Nt
Expedia
$34 Chicago, Illinois Spirit Airlines Tuesday and Wednesday Sale
DealBase.com
$91 Chicago, Illinois Book the Warwick Allerton Chicago 3 Nts in Jan Fr $91+/Nt
Save with Expedia, $30/night less
$227 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$85 Chicago, Illinois Book 4-Star Hilton Chicago in Chicago Fr $85+/Nt
Expedia
$34 Chicago, Illinois Spirit Airlines Tuesday and Wednesday Sale
DealBase.com
$130 Chicago, Illinois Special deal: 4-Star W Chicago - City Center Fr $130+/Nt
Expedia
$251 Chicago, Illinois Southwest Airlines Mexico and Caribbean Sale
DealBase.com
$92 Chicago, Illinois Book the Millennium Knickerbocker Chicago 3 Nts in Jan Fr $92+/Nt
Expedia
$126 Chicago, Illinois Southwest Airlines Touchdown for Less
DealBase.com
$64 Chicago, Illinois Jan deal: Chicago's Essex Inn Fr $64+/Nt
Save with Expedia, $11/night less
$179 Chicago, Illinois Virgin America Great Deals Across the US
DealBase.com
$119 Chicago, Illinois Book in Chicago: Save this Jan Fr $119+/Nt
Expedia
$63 Chicago, Illinois Spirit Airlines Tuesday and Wednesday Sale
DealBase.com
$59 Chicago, Illinois Red Roof Inn Chicago Downtown Magnificent Mile in Jan: $59 & Up
Save with Expedia, $11/night less
$200 Chicago, Illinois Virgin America Great Deals Across the US
DealBase.com
$61 Chicago, Illinois Chicago Savings! Book at Holiday Inn Express Cass Fr $61+/Nt
Expedia
$84 Chicago, Illinois Southwest Airlines Touchdown for Less
DealBase.com
$95 Chicago, Illinois Save in Chicago: Book 3 Nts in Jan Fr $95+/Nt
Expedia
$84 Chicago, Illinois Southwest Airlines Touchdown for Less
DealBase.com
$99 Chicago, Illinois Small budget: Book Chicago South Loop 3 Nts in Jan Fr $99+/Nt
Expedia
$200 Chicago, Illinois Virgin America Great Deals Across the US
DealBase.com
$112 Chicago, Illinois Book 4-Star Monaco Chicago - a Kimpton in Chicago Fr $112+/Nt
Save with Expedia, $27/night less
$34 Chicago, Illinois Spirit Airlines Tuesday and Wednesday Sale
DealBase.com
$129 Chicago, Illinois Jan deal: Chicago Marriott Downtown Magnificent Mile Fr $129+/Nt
Expedia
$114 Chicago, Illinois Southwest Airlines Touchdown for Less
DealBase.com
$272 Chicago, Illinois Jan deal: Trump International & Tower Chicago Fr $272+/Nt
Save with Expedia, $90/night less
$200 Chicago, Illinois Virgin America Great Deals Across the US
DealBase.com
$96 Chicago, Illinois Chicago Savings! Book at River Fr $96+/Nt
Save with Expedia, $10/night less
$34 Chicago, Illinois Spirit Airlines Tuesday and Wednesday Sale
DealBase.com
$145 Chicago, Illinois $145 & Up: Radisson Blu Aqua 4-Star Hotel in Chicago
Expedia
$114 Chicago, Illinois Southwest Airlines Touchdown for Less
DealBase.com
$194 Chicago, Illinois Book 3 Nts in Chicago this Jan Fr $194+/Nt
Expedia
$271 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$139 Chicago, Illinois Jan deal: theWit - A DoubleTree by Hilton Fr $139+/Nt
Expedia
$225 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$127 Chicago, Illinois Book in Chicago: Save at the Hard Rock Chicago in Jan Fr $127+/Nt
Save with Expedia, $22/night less
$34 Chicago, Illinois Spirit Airlines Tuesday and Wednesday Sale
DealBase.com
$130 Chicago, Illinois Chicago Savings! Book at The James Chicago Fr $130+/Nt
Save with Expedia, $33/night less
$375 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$99 Chicago, Illinois Embassy Suites Chicago Downtown in Jan: $99 & Up
Expedia
$89 Chicago, Illinois 45% Off Luxury Rooms on Mag Mile!
BookIt.com
$136 Chicago, Illinois Chicago Savings! Book 3 Nts in Jan Fr $136+/Nt
Save with Expedia, $13/night less
$38+ Chicago, Illinois Dolands Addition Vacation Rental Deals From $38
Tripping
$64 Chicago, Illinois Chicago Savings! Book at Travelodge Chicago Downtown Fr $64+/Nt
Expedia
$66 Chicago, Illinois Small budget: Stay in Chicago this Jan Fr $66+/Nt
Expedia
$104 Chicago, Illinois Chicago Savings! Book at Holiday Inn Chicago O'Hare Fr $104+/Nt
Expedia
$109 Chicago, Illinois Book in Chicago: Save this Jan Fr $109+/Nt
Expedia
$100 Chicago, Illinois Chicago Savings! Book 3 Nts in Jan Fr $100+/Nt
Expedia
PRICEDESTINATIONDEAL
$127 New York City, New York Cheap Flights from Washington, DC
DealBase.com
$199 New York City, New York Virgin America Great Deals Across the US
DealBase.com
$157 New York City, New York Cheap Flights from Chicago
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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