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Chicago, IL Hotel Deals

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Chicago, IL Hotel Deals

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TYPE PRICE DESTINATION DEAL
$88 Chicago, Illinois Chicago Savings! Book at MileNorth, A Chicago Fr $88+/Nt
Save with Expedia, $21/night less
$89 Chicago, Illinois 45% Off Luxury Rooms on Mag Mile!
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$88 Chicago, Illinois Small budget: Stay in Chicago this Jan Fr $88+/Nt
Expedia
$38+ Chicago, Illinois Dolands Addition Vacation Rental Deals From $38
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$324 Chicago, Illinois Save in Chicago: Book 3 Nts in Jan Fr $324+/Nt
Save with Expedia, $161/night less
$152 Chicago, Illinois Save at 4-Star Palomar Chicago, a Kimpton: $152 & Up in Jan
Save with Expedia, $7/night less
$99 Chicago, Illinois Book 3 Nts in Chicago this Jan Fr $99+/Nt
Expedia
$130 Chicago, Illinois Save Big This Jan! Book 3 Nts in Chicago at Raffaello Fr $130+/Nt
Save with Expedia, $69/night less
$160 Chicago, Illinois Jan deal: The Westin Chicago River North Fr $160+/Nt
Expedia
$96 Chicago, Illinois Book 3-Star Hampton Majestic Chicago Theatre District Fr $96+/Nt
Expedia
$129 Chicago, Illinois Book the Sheraton Chicago and Towers 3 Nts in Jan Fr $129+/Nt
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$345 Chicago, Illinois $345 & Up: Waldorf Astoria Chicago 5-Star Hotel in Chicago
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$117 Chicago, Illinois $117 & Up: Kinzie 3.5-Star Hotel in Chicago
Save with Expedia, $29/night less
$119 Chicago, Illinois Book 3-Star Residence Inn Chicago Downtown Fr $119+/Nt
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$287 Chicago, Illinois Save at 5-Star The Peninsula Chicago: $287 & Up in Jan
Save with Expedia, $143/night less
$127 Chicago, Illinois Chicago Savings! Book 3 Nts in Jan Fr $127+/Nt
Save with Expedia, $23/night less
$126 Chicago, Illinois Small budget: Stay in Chicago this Jan Fr $126+/Nt
Expedia
$101 Chicago, Illinois Jan deal: Holiday Inn Chicago Mart Plaza River North Fr $101+/Nt
Expedia
$169 Chicago, Illinois Small budget: Stay in Chicago this Jan Fr $169+/Nt
Expedia
$122 Chicago, Illinois Special deal: 4.5-Star InterContinental Chicago Fr $122+/Nt
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$78 Chicago, Illinois Chicago Savings! Book at BEST WESTERN Grant Park Fr $78+/Nt
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$76 Chicago, Illinois Doubletree by Hilton Chicago Magnificent Mile in Jan: $76 & Up
Expedia
$152 Chicago, Illinois Save Big This Jan! Book 3 Nts in Chicago Fr $152+/Nt
Expedia
$68 Chicago, Illinois Book 3 Nts in Chicago this Jan Fr $68+/Nt
Expedia
$119 Chicago, Illinois Book 4-Star The Palmer House Hilton Fr $119+/Nt
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$127 Chicago, Illinois Book 4-Star The Westin Michigan Avenue Chicago Fr $127+/Nt
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$81 Chicago, Illinois Jan deal: Homewood Suites by Hilton Chicago Downtown Fr $81+/Nt
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$91 Chicago, Illinois Book the Warwick Allerton Chicago 3 Nts in Jan Fr $91+/Nt
Save with Expedia, $30/night less
$85 Chicago, Illinois Book 4-Star Hilton Chicago in Chicago Fr $85+/Nt
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$130 Chicago, Illinois Special deal: 4-Star W Chicago - City Center Fr $130+/Nt
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$92 Chicago, Illinois Book the Millennium Knickerbocker Chicago 3 Nts in Jan Fr $92+/Nt
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$64 Chicago, Illinois Jan deal: Chicago's Essex Inn Fr $64+/Nt
Save with Expedia, $11/night less
$119 Chicago, Illinois Book in Chicago: Save this Jan Fr $119+/Nt
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$59 Chicago, Illinois Red Roof Inn Chicago Downtown Magnificent Mile in Jan: $59 & Up
Save with Expedia, $11/night less
$61 Chicago, Illinois Chicago Savings! Book at Holiday Inn Express Cass Fr $61+/Nt
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$95 Chicago, Illinois Save in Chicago: Book 3 Nts in Jan Fr $95+/Nt
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$99 Chicago, Illinois Small budget: Book Chicago South Loop 3 Nts in Jan Fr $99+/Nt
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$112 Chicago, Illinois Book 4-Star Monaco Chicago - a Kimpton in Chicago Fr $112+/Nt
Save with Expedia, $27/night less
$129 Chicago, Illinois Jan deal: Chicago Marriott Downtown Magnificent Mile Fr $129+/Nt
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$272 Chicago, Illinois Jan deal: Trump International & Tower Chicago Fr $272+/Nt
Save with Expedia, $90/night less
$145 Chicago, Illinois $145 & Up: Radisson Blu Aqua 4-Star Hotel in Chicago
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$194 Chicago, Illinois Book 3 Nts in Chicago this Jan Fr $194+/Nt
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$139 Chicago, Illinois Jan deal: theWit - A DoubleTree by Hilton Fr $139+/Nt
Expedia
$127 Chicago, Illinois Book in Chicago: Save at the Hard Rock Chicago in Jan Fr $127+/Nt
Save with Expedia, $22/night less
$130 Chicago, Illinois Chicago Savings! Book at The James Chicago Fr $130+/Nt
Save with Expedia, $33/night less
$99 Chicago, Illinois Embassy Suites Chicago Downtown in Jan: $99 & Up
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$136 Chicago, Illinois Chicago Savings! Book 3 Nts in Jan Fr $136+/Nt
Save with Expedia, $13/night less
$64 Chicago, Illinois Chicago Savings! Book at Travelodge Chicago Downtown Fr $64+/Nt
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$119 Chicago, Illinois Chicago Savings! Book at Hyatt Regency Chicago Fr $119+/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
$82 Chicago, Illinois Save at 3-Star Holiday Inn Chicago Downtown: $82 & Up in Jan
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$97 Chicago, Illinois Chicago Savings! Book at BEST WESTERN River North Fr $97+/Nt
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$110 Chicago, Illinois Jan deal: La Quinta Inn & Suites Chicago Downtown Fr $110+/Nt
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$70 Chicago, Illinois Save in Chicago: Book 3 Nts in Jan at Congress Plaza Fr $70+/Nt
Save with Expedia, $17/night less
$129 Chicago, Illinois Chicago Savings! Book at W Chicago Lakeshore Fr $129+/Nt
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$90 Chicago, Illinois Book in Chicago: Save this Jan Fr $90+/Nt
Save with Expedia, $9/night less
$139 Chicago, Illinois Chicago Savings! Book at The Drake Fr $139+/Nt
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$119 Chicago, Illinois $119 & Up: Hilton Chicago O'Hare Airport 4-Star Hotel in Chicago
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$79 Chicago, Illinois Chicago Savings! Book 3 Nts in Jan Fr $79+/Nt
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$175 Chicago, Illinois Book 4-Star PUBLIC Chicago Fr $175+/Nt
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$81 Chicago, Illinois Book 3.5-Star Club Quarters Chicago - Central Loop Fr $81+/Nt
Save with Expedia, $8/night less
$138 Chicago, Illinois Save Big This Jan! Book 3 Nts in Chicago Fr $138+/Nt
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$108 Chicago, Illinois Chicago Savings! Book at Buckingham Athletic Club Fr $108+/Nt
Save with Expedia, $71/night less
$72 Chicago, Illinois Book in Chicago: Save this Jan Fr $72+/Nt
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$117 Chicago, Illinois Jan deal: Hyatt Chicago Magnificent Mile Fr $117+/Nt
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$123 Chicago, Illinois Save Big This Jan! Book 3 Nts in Chicago Fr $123+/Nt
Save with Expedia, $6/night less
$93 Chicago, Illinois Jan deal: Crowne Plaza Chicago - The Metro Fr $93+/Nt
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$111 Chicago, Illinois Book in Chicago: Save this Jan Fr $111+/Nt
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$65 Chicago, Illinois Small budget: Stay in Chicago this Jan Fr $65+/Nt
Expedia
$133 Chicago, Illinois Small budget: Book Burnham - a Kimpton 3 Nts in Jan Fr $133+/Nt
Save with Expedia, $6/night less
$204 Chicago, Illinois Jan deal: Fairfield Inn Chicago Midway Airport Fr $204+/Nt
Expedia
$76 Chicago, Illinois Small budget: Stay in Chicago this Jan Fr $76+/Nt
Save with Expedia, $13/night less
$259 Chicago, Illinois Jan deal: Park Hyatt Chicago Fr $259+/Nt
Expedia
$99 Chicago, Illinois Chicago Savings! Book 3 Nts in Jan Fr $99+/Nt
Expedia
$110 Chicago, Illinois The Silversmith on Sale: Book 3 Nts in Jan Fr $110+/Nt
Save with Expedia, $19/night less
$193 Chicago, Illinois Renaissance Chicago O'Hare Suites in Jan: $193 & Up
Expedia
$96 Chicago, Illinois Special deal: 3-Star Comfort Suites Michigan Avenue Fr $96+/Nt
Expedia
$119 Chicago, Illinois Special deal: 4-Star The Whitehall Fr $119+/Nt
Expedia
$284 Chicago, Illinois Book the Four Seasons Chicago 3 Nts in Jan Fr $284+/Nt
Save with Expedia, $141/night less
$136 Chicago, Illinois Chicago Savings! Book 3 Nts in Jan Fr $136+/Nt
Save with Expedia, $23/night less
$119 Chicago, Illinois Save Big This Jan! Book 3 Nts in Chicago Fr $119+/Nt
Save with Expedia, $20/night less
$165 Chicago, Illinois Save in Chicago: Book 3 Nts in Jan at Conrad Chicago Fr $165+/Nt
Expedia
$109 Chicago, Illinois Book 3 Nts in Chicago this Jan Fr $109+/Nt
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$96 Chicago, Illinois Chicago Savings! Book at River Fr $96+/Nt
Save with Expedia, $10/night less
$35+ Oak Park, Illinois Oak Park Vacation Rental Deals From $35
Tripping
$76 Burbank, Illinois BEST WESTERN Inn & Suites - Midway Airport in Jan: $76 & Up
Save with Expedia, $19/night less
$50+ Evanston, Illinois Evanston Vacation Rental Deals From $50
Tripping
$76 Westchester, Illinois Book in Westchester: Save this Jan Fr $76+/Nt
Expedia
$59+ Elmhurst, Illinois Elmhurst Vacation Rental Deals From $59
Tripping
$73 Countryside, Illinois Small budget: Stay in Countryside this Jan Fr $73+/Nt
Save with Expedia, $18/night less
$43+ Downers Grove, Illinois Downers Grove Vacation Rental Deals From $43
Tripping
$96 Schiller Park, Illinois Four Points by Sheraton Chicago O'Hare Airport in Jan: $96 & Up
Expedia
$57 Schiller Park, Illinois Schiller Park Savings! Book at O'Hare Inn & Suites Fr $57+/Nt
Save with Expedia, $38/night less
$95 Schiller Park, Illinois Save in Schiller Park: Book 3 Nts in Jan Fr $95+/Nt
Expedia
$115 Alsip, Illinois Alsip Savings! Book at Doubletree Chicago / Alsip Fr $115+/Nt
Expedia
$93 Skokie, Illinois Book in Skokie: Save this Jan Fr $93+/Nt
Expedia
$94 Crestwood, Illinois Holiday Inn Express Crestwood in Jan: $94 & Up
Expedia
PRICEDESTINATIONDEAL
$127 New York City, New York Cheap Flights from Washington, DC
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$157 New York City, New York Delta US Fare Sale
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$119 New York City, New York Virgin America Great Deals Across the US
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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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