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Chicago, IL Hotel Deals

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Chicago, IL Hotel Deals

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TYPE PRICE DESTINATION DEAL
$244 Chicago, Illinois Jan deal: Park Hyatt Chicago Fr $244+/Nt
Expedia
$38+ Chicago, Illinois Dolands Addition Vacation Rental Deals From $38
Tripping
$119 Chicago, Illinois Small budget: Stay in Chicago this Jan Fr $119+/Nt
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$119 Chicago, Illinois Jan deal: Residence Inn Chicago Downtown Fr $119+/Nt
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$297 Chicago, Illinois The Peninsula Chicago in Jan: $297 & Up
Save with Expedia, $148/night less
$93 Chicago, Illinois Book 3-Star Hampton Inn & Suites Chicago - Downtown Fr $93+/Nt
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$85 Chicago, Illinois Small budget: Book Hilton Chicago 3 Nts in Jan Fr $85+/Nt
Expedia
$104 Chicago, Illinois Save in Chicago: Book 3 Nts in Jan Fr $104+/Nt
Expedia
$106 Chicago, Illinois Book 3 Nts in Chicago this Jan Fr $106+/Nt
Expedia
$119 Chicago, Illinois Hilton Chicago O'Hare Airport in Jan: $119 & Up
Expedia
$104 Chicago, Illinois Chicago Savings! Book at BEST WESTERN River North Fr $104+/Nt
Expedia
$88 Chicago, Illinois Book 4-Star Chicago Downtown, Autograph Collection Fr $88+/Nt
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$136 Chicago, Illinois Book 4.5-Star Omni Chicago in Chicago Fr $136+/Nt
Save with Expedia, $23/night less
$119 Chicago, Illinois Book in Chicago: Save this Jan Fr $119+/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
$86 Chicago, Illinois Small budget: Stay in Chicago this Jan Fr $86+/Nt
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$109 Chicago, Illinois Book 4-Star The Westin Michigan Avenue Chicago Fr $109+/Nt
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$133 Chicago, Illinois Book in Chicago: Save at the Swissotel Chicago in Jan Fr $133+/Nt
Save with Expedia, $23/night less
$179 Chicago, Illinois Book 4-Star JW Marriott Chicago Fr $179+/Nt
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$109 Chicago, Illinois Small budget: Stay in Chicago this Jan Fr $109+/Nt
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$97 Chicago, Illinois Save at 3.5-Star Blake Chicago: $97 & Up in Jan
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$82 Chicago, Illinois Book 3.5-Star Buckingham Athletic Club in Chicago Fr $82+/Nt
Save with Expedia, $54/night less
$54 Chicago, Illinois Chicago Savings! Book 3 Nts in Jan Fr $54+/Nt
Save with Expedia, $29/night less
$110 Chicago, Illinois Save at 4-Star The Whitehall: $110 & Up in Jan
Save with Expedia, $19/night less
$130 Chicago, Illinois Book 4.5-Star The James Chicago in Chicago Fr $130+/Nt
Save with Expedia, $33/night less
$86 Chicago, Illinois Book the Hyatt Regency McCormick Place 3 Nts in Jan Fr $86+/Nt
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$82 Chicago, Illinois Small budget: Stay in Chicago this Jan Fr $82+/Nt
Save with Expedia, $14/night less
$106 Chicago, Illinois Kinzie on Sale: Book 3 Nts in Jan Fr $106+/Nt
Save with Expedia, $27/night less
$66 Chicago, Illinois Small budget: Book ACME Company Chicago 3 Nts in Jan Fr $66+/Nt
Save with Expedia, $30/night less
$74 Chicago, Illinois Book in Chicago: Save this Jan Fr $74+/Nt
Save with Expedia, $13/night less
$81 Chicago, Illinois Book 3 Nts in Chicago this Jan Fr $81+/Nt
Save with Expedia, $20/night less
$96 Chicago, Illinois Chicago Savings! Book at MileNorth, A Chicago Fr $96+/Nt
Save with Expedia, $23/night less
$81 Chicago, Illinois Jan deal: Homewood Suites by Hilton Chicago Downtown Fr $81+/Nt
Expedia
$127 Chicago, Illinois $127 & Up: W Chicago Lakeshore 4-Star Hotel in Chicago
Expedia
$138 Chicago, Illinois Book in Chicago: Save this Jan Fr $138+/Nt
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$130 Chicago, Illinois Save Big This Jan! Book 3 Nts at Raffaello Fr $130+/Nt
Save with Expedia, $69/night less
$74 Chicago, Illinois Indigo Chicago Downtown Gold Coast in Jan: $74 & Up
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$99 Chicago, Illinois Chicago Savings! Book at Chicago South Loop Fr $99+/Nt
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$114 Chicago, Illinois Courtyard Chicago Downtown/Magnificent Mile in Jan: $114 & Up
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$290 Chicago, Illinois Trump International & Tower Chicago in Jan: $290 & Up
Save with Expedia, $72/night less
$121 Chicago, Illinois Jan deal: Wyndham Grand Chicago Riverfront Fr $121+/Nt
Save with Expedia, $12/night less
$133 Chicago, Illinois Book in Chicago: Save at the dana and spa in Jan Fr $133+/Nt
Expedia
$75 Chicago, Illinois Chicago Savings! Book at Holiday Inn Express Cass Fr $75+/Nt
Expedia
$90 Chicago, Illinois Jan deal: Hampton Majestic Chicago Theatre District Fr $90+/Nt
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$142 Chicago, Illinois Jan deal: Sheraton Chicago and Towers Fr $142+/Nt
Expedia
$74 Chicago, Illinois The Tremont Chicago at Magnificent Mile in Jan: $74 & Up
Expedia
$70 Chicago, Illinois Book 3-Star Chicago's Essex Inn in Chicago Fr $70+/Nt
Save with Expedia, $12/night less
$106 Chicago, Illinois Book the Comfort Suites Michigan Avenue 3 Nts in Jan Fr $106+/Nt
Expedia
$119 Chicago, Illinois Small budget: Stay in Chicago this Jan Fr $119+/Nt
Expedia
$153 Chicago, Illinois Save in Chicago: Book 3 Nts in Jan Fr $153+/Nt
Expedia
$68 Chicago, Illinois Save Big This Jan! Book 3 Nts in Chicago Fr $68+/Nt
Expedia
$102 Chicago, Illinois Chicago Savings! Book 3 Nts in Jan Fr $102+/Nt
Expedia
$75 Chicago, Illinois Jan deal: Warwick Allerton Chicago Fr $75+/Nt
Save with Expedia, $42/night less
$116 Chicago, Illinois Chicago Marriott at Medical District/UIC in Jan: $116 & Up
Expedia
$97 Chicago, Illinois Chicago Savings! Book 3 Nts in Jan Fr $97+/Nt
Expedia
$81 Chicago, Illinois Chicago Savings! Book 3 Nts in Jan at Central Loop Fr $81+/Nt
Save with Expedia, $8/night less
$133 Chicago, Illinois Save in Chicago: Book 3 Nts in Jan Fr $133+/Nt
Expedia
$176 Chicago, Illinois Book 3.5-Star Renaissance Chicago O'Hare Suites Fr $176+/Nt
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$159 Chicago, Illinois Special deal: 3.5-Star Renaissance Chicago Fr $159+/Nt
Expedia
$113 Chicago, Illinois Save Big This Jan! Book 3 Nts in Chicago Fr $113+/Nt
Expedia
$93 Chicago, Illinois Book in Chicago: Save this Jan Fr $93+/Nt
Expedia
$90 Chicago, Illinois Save at 3.5-Star River: $90 & Up in Jan
Save with Expedia, $9/night less
$82 Chicago, Illinois Chicago Savings! Book 3 Nts in Jan Fr $82+/Nt
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$133 Chicago, Illinois Palomar Chicago, a Kimpton in Jan: $133 & Up
Save with Expedia, $6/night less
$292 Chicago, Illinois The Ritz-Carlton Chicago (A Four Seasons ) in Jan: $292 & Up
Save with Expedia, $73/night less
$133 Chicago, Illinois Burnham - a Kimpton in Jan: $133 & Up
Save with Expedia, $6/night less
$139 Chicago, Illinois Book 4-Star The Drake in Chicago Fr $139+/Nt
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$78 Chicago, Illinois Chicago Savings! Book at BEST WESTERN Grant Park Fr $78+/Nt
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$80 Chicago, Illinois Save at 4-Star Millennium Knickerbocker Chicago: $80 & Up in Jan
Expedia
$123 Chicago, Illinois Allegro Chicago - a Kimpton in Jan: $123 & Up
Save with Expedia, $6/night less
$136 Chicago, Illinois Book 3 Nts in Chicago this Jan Fr $136+/Nt
Save with Expedia, $23/night less
$115 Chicago, Illinois Jan deal: theWit - A DoubleTree by Hilton Fr $115+/Nt
Expedia
$133 Chicago, Illinois Special deal: 4-Star Monaco Chicago - a Kimpton Fr $133+/Nt
Save with Expedia, $6/night less
$110 Chicago, Illinois Save at 3.5-Star The Silversmith: $110 & Up in Jan
Save with Expedia, $19/night less
$311 Chicago, Illinois Chicago Savings! Book at Waldorf Astoria Chicago Fr $311+/Nt
Expedia
$90 Chicago, Illinois Chicago Savings! Book 3 Nts in Jan Fr $90+/Nt
Expedia
$55 Chicago, Illinois Chicago Savings! Book at Travelodge Chicago Downtown Fr $55+/Nt
Expedia
$284 Chicago, Illinois Special deal: 5-Star Four Seasons Chicago Fr $284+/Nt
Save with Expedia, $141/night less
$76 Chicago, Illinois Doubletree by Hilton Chicago Magnificent Mile in Jan: $76 & Up
Expedia
$127 Chicago, Illinois Save in Chicago: Book 3 Nts in Jan Fr $127+/Nt
Save with Expedia, $22/night less
$129 Chicago, Illinois Book in Chicago: Save this Jan Fr $129+/Nt
Expedia
$119 Chicago, Illinois Book the Hyatt Regency Chicago 3 Nts in Jan Fr $119+/Nt
Expedia
$117 Chicago, Illinois Save Big This Jan! Book 3 Nts in Chicago Fr $117+/Nt
Expedia
$70 Chicago, Illinois Chicago Savings! Book 3 Nts in Jan at Congress Plaza Fr $70+/Nt
Save with Expedia, $17/night less
$35+ Oak Park, Illinois Oak Park Vacation Rental Deals From $35
Tripping
$105 Addison, Illinois Hilton Garden Inn Addison on Sale: Book 3 Nts in Jan Fr $105+/Nt
Expedia
$43+ Downers Grove, Illinois Downers Grove Vacation Rental Deals From $43
Tripping
$87 Addison, Illinois Addison Savings! Book at Hampton Inn & Suites Addison Fr $87+/Nt
Expedia
$59+ Elmhurst, Illinois Elmhurst Vacation Rental Deals From $59
Tripping
$119 Arlington Heights, Illinois Save Big This Jan! Book 3 Nts in Arlington Heights Fr $119+/Nt
Expedia
$50+ Evanston, Illinois Evanston Vacation Rental Deals From $50
Tripping
$54 Arlington Heights, Illinois Jameson Suites of Arlington Heights in Jan: $54 & Up
Save with Expedia, $18/night less
$116 Bloomingdale, Illinois Courtyard by Marriott Chicago Bloomingdale in Jan: $116 & Up
Expedia
$109 Bloomingdale, Illinois Book in Bloomingdale: Save this Jan Fr $109+/Nt
Expedia
$86 Bolingbrook, Illinois Book 3 Nts in Bolingbrook this Jan Fr $86+/Nt
Expedia
$62 Bridgeview, Illinois Save Big This Jan! Book 3 Nts in Bridgeview Fr $62+/Nt
Expedia
$94 Crestwood, Illinois Jan deal: Holiday Inn Express Crestwood Fr $94+/Nt
Expedia
$99 Deerfield, Illinois Deerfield Savings! Book 3 Nts in Jan Fr $99+/Nt
Expedia
$85 Des Plaines, Illinois Book 3-Star Hilton Garden Inn Chicago O'Hare Airport Fr $85+/Nt
Expedia
$109 Downers Grove, Illinois Book in Downers Grove: Save this Jan Fr $109+/Nt
Expedia
PRICEDESTINATIONDEAL
$117 New York City, New York Cheap Flights from Washington, DC
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$178 New York City, New York Cheap Flights from Ft. Lauderdale
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$236 New York City, New York Cheap Flights from Houston
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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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