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Chicago, IL Hotel Deals

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Chicago, IL Hotel Deals

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TYPE PRICE DESTINATION DEAL
$85+ Chicago, Illinois 4-Star Chicago Hotels from $85
trivago
$79 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $79+/Nt
Expedia
$522 Chicago, Illinois Great Rates in Chicago + Breakfast!
DealBase.com
$204 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $204+/Nt
Expedia
$125+ Chicago, Illinois Chicago on Sale! Starting From $125/nt
Jetsetter
$113 Chicago, Illinois Book 4-Star Hilton Chicago in Chicago Fr $113+/Nt
Expedia
$112+ Chicago, Illinois 4.5 Star Luxury Chicago Hotel on Sale! Starting from $112/nt
Jetsetter
$336 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $336+/Nt
Save with Expedia, $60/night less
$116 Chicago, Illinois Chicago Marriott at Medical District/UIC in Oct: $116 & Up
Expedia
$256 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $256+/Nt
Expedia
$144 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $144+/Nt
Save with Expedia, $15/night less
$72 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $72+/Nt
Save with Expedia, $18/night less
$109 Chicago, Illinois Book 3-Star Holiday Inn Express Cass Fr $109+/Nt
Expedia
$130 Chicago, Illinois Special deal: 4-Star W Chicago Lakeshore Fr $130+/Nt
Expedia
$199 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $199+/Nt
Expedia
$109 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $109+/Nt
Expedia
$179 Chicago, Illinois Chicago Savings! Book at The Blackstone A Renaissance Fr $179+/Nt
Expedia
$136 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $136+/Nt
Expedia
$109 Chicago, Illinois $109 & Up: Blake Chicago 3.5-Star Hotel in Chicago
Expedia
$150 Chicago, Illinois Chicago Savings! Book at Radisson Blu Aqua Fr $150+/Nt
Expedia
$156 Chicago, Illinois Save at 4.5-Star Sofitel Chicago Water Tower: $156 & Up in Oct
Expedia
$297 Chicago, Illinois Book 5-Star Trump International & Tower Chicago Fr $297+/Nt
Save with Expedia, $98/night less
$96 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $96+/Nt
Expedia
$119 Chicago, Illinois Crowne Plaza Chicago - The Metro in Oct: $119 & Up
Save with Expedia, $7/night less
$85 Chicago, Illinois Chicago Savings! Book at ACME Company Chicago Fr $85+/Nt
Save with Expedia, $14/night less
$123 Chicago, Illinois Doubletree by Hilton Chicago Magnificent Mile in Oct: $123 & Up
Expedia
$126 Chicago, Illinois Save at 4.5-Star The James Chicago: $126 & Up in Oct
Save with Expedia, $83/night less
$103 Chicago, Illinois Book 3-Star Hampton Majestic Chicago Theatre District Fr $103+/Nt
Expedia
$164 Chicago, Illinois Residence Inn Chicago Downtown / River North in Oct: $164 & Up
Expedia
$102 Chicago, Illinois Oct deal: Millennium Knickerbocker Chicago Fr $102+/Nt
Save with Expedia, $17/night less
$136 Chicago, Illinois Book in Chicago: Save at the Kinzie in Oct Fr $136+/Nt
Expedia
$116 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct at Felix Fr $116+/Nt
Save with Expedia, $21/night less
$110 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $110+/Nt
Expedia
$99 Chicago, Illinois Chicago Savings! Book at Chicago South Loop Fr $99+/Nt
Expedia
$109 Chicago, Illinois Embassy Suites Chicago Downtown Lakefront in Oct: $109 & Up
Expedia
$299 Chicago, Illinois Book the Waldorf Astoria Chicago 3 Nts in Oct Fr $299+/Nt
Expedia
$122 Chicago, Illinois Holiday Inn Chicago O'Hare on Sale: Book 3 Nts in Oct Fr $122+/Nt
Expedia
$134 Chicago, Illinois Book in Chicago: Save this Oct Fr $134+/Nt
Expedia
$121 Chicago, Illinois Warwick Allerton Chicago on Sale: Book 3 Nts in Oct Fr $121+/Nt
Save with Expedia, $82/night less
$127 Chicago, Illinois Wyndham Grand Chicago Riverfront in Oct: $127 & Up
Save with Expedia, $22/night less
$85 Chicago, Illinois Book in Chicago: Save this Oct Fr $85+/Nt
Save with Expedia, $14/night less
$159 Chicago, Illinois Book in Chicago: Save this Oct Fr $159+/Nt
Expedia
$110 Chicago, Illinois Chicago Savings! Book at Burnham - a Kimpton Fr $110+/Nt
Save with Expedia, $19/night less
$127 Chicago, Illinois Save at 4-Star The Westin Chicago River North: $127 & Up in Oct
Expedia
$161 Chicago, Illinois Monaco Chicago - a Kimpton in Oct: $161 & Up
Save with Expedia, $69/night less
$144 Chicago, Illinois The Silversmith on Sale: Book 3 Nts in Oct Fr $144+/Nt
Save with Expedia, $25/night less
$169 Chicago, Illinois Save Big This Oct! Book 3 Nts at Conrad Chicago Fr $169+/Nt
Expedia
$115 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $115+/Nt
Expedia
$147 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $147+/Nt
Save with Expedia, $26/night less
$81 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $81+/Nt
Save with Expedia, $8/night less
$85 Chicago, Illinois Book 3-Star Hampton Inn & Suites Chicago - Downtown Fr $85+/Nt
Expedia
$94 Chicago, Illinois $94 & Up: Hyatt Regency Chicago 4-Star Hotel in Chicago
Expedia
$139 Chicago, Illinois Oct deal: Hilton Chicago O'Hare Airport Fr $139+/Nt
Expedia
$149 Chicago, Illinois Hyatt Chicago Magnificent Mile in Oct: $149 & Up
Expedia
$85 Chicago, Illinois Oct deal: Crowne Plaza Chicago Magnificent Mile Fr $85+/Nt
Expedia
$87 Chicago, Illinois Indigo Chicago Downtown Gold Coast in Oct: $87 & Up
Expedia
$171 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $171+/Nt
Save with Expedia, $42/night less
$104 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $104+/Nt
Expedia
$137 Chicago, Illinois Book 4-Star Chicago Downtown, Autograph Collection Fr $137+/Nt
Save with Expedia, $46/night less
$123 Chicago, Illinois Book in Chicago: Save at the River in Oct Fr $123+/Nt
Expedia
$106 Chicago, Illinois Book in Chicago: Save at the Central Loop in Oct Fr $106+/Nt
Expedia
$90 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $90+/Nt
Expedia
$109 Chicago, Illinois Sheraton Chicago and Towers in Oct: $109 & Up
Expedia
$317 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $317+/Nt
Save with Expedia, $158/night less
$140 Chicago, Illinois Oct deal: La Quinta Inn & Suites Chicago Downtown Fr $140+/Nt
Expedia
$129 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $129+/Nt
Expedia
$90 Chicago, Illinois BEST WESTERN River North in Oct: $90 & Up
Expedia
$119 Chicago, Illinois Comfort Suites Michigan Avenue in Oct: $119 & Up
Expedia
$108 Chicago, Illinois Book the Raffaello 3 Nts in Oct Fr $108+/Nt
Save with Expedia, $58/night less
$102 Chicago, Illinois InterContinental Chicago on Sale: Book 3 Nts in Oct Fr $102+/Nt
Expedia
$166 Chicago, Illinois Chicago Savings! Book at Renaissance Chicago Fr $166+/Nt
Expedia
$74 Chicago, Illinois Book in Chicago: Save this Oct Fr $74+/Nt
Expedia
$108 Chicago, Illinois Save Big This Oct! Book 3 Nts at PUBLIC Chicago Fr $108+/Nt
Save with Expedia, $57/night less
$99 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $99+/Nt
Expedia
$115 Chicago, Illinois Small budget: Book Days Inn Chicago 3 Nts in Oct Fr $115+/Nt
Expedia
$128 Chicago, Illinois Oct deal: Courtyard Chicago Downtown/Magnificent Mile Fr $128+/Nt
Expedia
$236 Chicago, Illinois Book 3.5-Star Renaissance Chicago O'Hare Suites Fr $236+/Nt
Expedia
$80 Chicago, Illinois Chicago Savings! Book at BEST WESTERN Grant Park Fr $80+/Nt
Save with Expedia, $20/night less
$103 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $103+/Nt
Expedia
$129 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $129+/Nt
Expedia
$96 Chicago, Illinois Small budget: Book The Whitehall 3 Nts in Oct Fr $96+/Nt
Save with Expedia, $23/night less
$292 Chicago, Illinois $292 & Up: Park Hyatt Chicago 5-Star Hotel in Chicago
Expedia
$127 Chicago, Illinois Special deal: 4-Star Hard Rock Chicago Fr $127+/Nt
Save with Expedia, $22/night less
$128 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct at Omni Chicago Fr $128+/Nt
Save with Expedia, $31/night less
$356 Chicago, Illinois Book in Chicago: Save this Oct Fr $356+/Nt
Save with Expedia, $39/night less
$109 Chicago, Illinois Chicago Savings! Book at Holiday Inn Chicago Downtown Fr $109+/Nt
Expedia
$123 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $123+/Nt
Expedia
$95 Chicago, Illinois Save at 3.5-Star Embassy Suites Chicago Downtown: $95 & Up in Oct
Expedia
$153 Chicago, Illinois Book the W Chicago - City Center 3 Nts in Oct Fr $153+/Nt
Expedia
$159 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $159+/Nt
Expedia
$110 Chicago, Illinois The Westin Michigan Avenue Chicago in Oct: $110 & Up
Expedia
$68 Chicago, Illinois Oct deal: The Tremont Chicago at Magnificent Mile Fr $68+/Nt
Expedia
$129 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $129+/Nt
Expedia
$159 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $159+/Nt
Expedia
$95 Lisle, Illinois Book 3.5-Star Hilton Lisle / Naperville Fr $95+/Nt
Expedia
$82 Deerfield, Illinois Small budget: Stay in Deerfield this Oct Fr $82+/Nt
Save with Expedia, $27/night less
$126 Evanston, Illinois Hilton Garden Inn Evanston in Oct: $126 & Up
Expedia
$76 Westchester, Illinois Book 3 Nts in Westchester this Oct Fr $76+/Nt
Expedia
$104 Tinley Park, Illinois Oct deal: Hilton Garden Inn Chicago/Tinley Park Fr $104+/Nt
Expedia
$145 Bedford Park, Illinois Book in Bedford Park: Save this Oct Fr $145+/Nt
Expedia
PRICEDESTINATIONDEAL
$118 New York City, New York Cheap Flights from Washington, DC
DealBase.com
$177 New York City, New York Cheap Flights from Chicago
DealBase.com
$297 New York City, New York Cheap Flights from Portland
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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