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Chicago, IL Hotel Deals

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Chicago, IL Hotel Deals

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TYPE PRICE DESTINATION DEAL
$173 Chicago, Illinois Oct deal: Residence Inn Chicago Downtown Fr $173+/Nt
Expedia
$522 Chicago, Illinois Great Rates in Chicago + Breakfast!
DealBase.com
$385 Chicago, Illinois $385 & Up: Four Seasons Chicago 5-Star Hotel in Chicago
Expedia
$125+ Chicago, Illinois Chicago on Sale! Starting From $125/nt
Jetsetter
$161 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $161+/Nt
Expedia
$85+ Chicago, Illinois 4-Star Chicago Hotels from $85
trivago
$133 Chicago, Illinois Chicago Savings! Book at Raffaello Fr $133+/Nt
Save with Expedia, $71/night less
$112+ Chicago, Illinois 4.5 Star Luxury Chicago Hotel on Sale! Starting from $112/nt
Jetsetter
$188 Chicago, Illinois Chicago Savings! Book at The Blackstone A Renaissance Fr $188+/Nt
Expedia
$139 Chicago, Illinois Book 3.5-Star Kinzie in Chicago Fr $139+/Nt
Expedia
$114 Chicago, Illinois Special deal: 3-Star BEST WESTERN River North Fr $114+/Nt
Expedia
$167 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $167+/Nt
Save with Expedia, $29/night less
$133 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $133+/Nt
Expedia
$127 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $127+/Nt
Save with Expedia, $68/night less
$144 Chicago, Illinois Special deal: 3.5-Star The Silversmith Fr $144+/Nt
Save with Expedia, $25/night less
$152 Chicago, Illinois Book 3.5-Star Embassy Suites Chicago Downtown Fr $152+/Nt
Expedia
$183 Chicago, Illinois Book the Buckingham Athletic Club 3 Nts in Oct Fr $183+/Nt
Expedia
$127 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $127+/Nt
Save with Expedia, $22/night less
$90 Chicago, Illinois Oct deal: Indigo Chicago Downtown Gold Coast Fr $90+/Nt
Expedia
$192 Chicago, Illinois Small budget: Book Omni Chicago 3 Nts in Oct Fr $192+/Nt
Save with Expedia, $47/night less
$161 Chicago, Illinois Monaco Chicago - a Kimpton in Oct: $161 & Up
Save with Expedia, $69/night less
$116 Chicago, Illinois Holiday Inn Express Cass on Sale: Book 3 Nts in Oct Fr $116+/Nt
Expedia
$129 Chicago, Illinois Book 3-Star Hampton Inn & Suites Chicago - Downtown Fr $129+/Nt
Expedia
$149 Chicago, Illinois Book 3-Star Hampton Majestic Chicago Theatre District Fr $149+/Nt
Expedia
$140 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $140+/Nt
Expedia
$138 Chicago, Illinois Chicago Savings! Book at Warwick Allerton Chicago Fr $138+/Nt
Save with Expedia, $65/night less
$166 Chicago, Illinois Oct deal: Sofitel Chicago Water Tower Fr $166+/Nt
Expedia
$103 Chicago, Illinois Oct deal: Hostelling International Chicago Fr $103+/Nt
Expedia
$136 Chicago, Illinois Embassy Suites Chicago Downtown Lakefront in Oct: $136 & Up
Expedia
$143 Chicago, Illinois La Quinta Inn & Suites Chicago Downtown in Oct: $143 & Up
Expedia
$115 Chicago, Illinois Book 4-Star theWit - A DoubleTree by Hilton Fr $115+/Nt
Expedia
$260 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $260+/Nt
Expedia
$88 Chicago, Illinois Chicago Savings! Book at InterContinental Chicago Fr $88+/Nt
Expedia
$136 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $136+/Nt
Save with Expedia, $24/night less
$171 Chicago, Illinois Doubletree by Hilton Chicago Magnificent Mile in Oct: $171 & Up
Expedia
$119 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $119+/Nt
Expedia
$96 Chicago, Illinois Book in Chicago: Save this Oct Fr $96+/Nt
Expedia
$159 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $159+/Nt
Expedia
$129 Chicago, Illinois Chicago Savings! Book at MileNorth, A Chicago Fr $129+/Nt
Expedia
$99 Chicago, Illinois Oct deal: Chicago South Loop Fr $99+/Nt
Expedia
$136 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $136+/Nt
Save with Expedia, $23/night less
$106 Chicago, Illinois Book in Chicago: Save this Oct Fr $106+/Nt
Expedia
$127 Chicago, Illinois Book in Chicago: Save this Oct Fr $127+/Nt
Expedia
$150 Chicago, Illinois Fairmont Chicago Millennium Park in Oct: $150 & Up
Save with Expedia, $16/night less
$99 Chicago, Illinois Chicago Savings! Book at Blake Chicago Fr $99+/Nt
Expedia
$96 Chicago, Illinois Special deal: 4-Star The Whitehall Fr $96+/Nt
Save with Expedia, $23/night less
$128 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $128+/Nt
Expedia
$127 Chicago, Illinois $127 & Up: Hard Rock Chicago 4-Star Hotel in Chicago
Save with Expedia, $22/night less
$142 Chicago, Illinois Oct deal: Homewood Suites by Hilton Chicago Downtown Fr $142+/Nt
Expedia
$109 Chicago, Illinois Book 4-Star Sheraton Chicago and Towers in Chicago Fr $109+/Nt
Expedia
$93 Chicago, Illinois Book in Chicago: Save this Oct Fr $93+/Nt
Expedia
$78 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $78+/Nt
Save with Expedia, $51/night less
$313 Chicago, Illinois Book 5-Star Trump International & Tower Chicago Fr $313+/Nt
Save with Expedia, $78/night less
$94 Chicago, Illinois Book in Chicago: Save this Oct Fr $94+/Nt
Expedia
$203 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $203+/Nt
Expedia
$126 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $126+/Nt
Expedia
$198 Chicago, Illinois Book in Chicago: Save this Oct Fr $198+/Nt
Expedia
$119 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $119+/Nt
Save with Expedia, $20/night less
$209 Chicago, Illinois Chicago Savings! Book at Conrad Chicago Fr $209+/Nt
Expedia
$129 Chicago, Illinois Book 3.5-Star Crowne Plaza Chicago - The Metro Fr $129+/Nt
Expedia
$370 Chicago, Illinois The Peninsula Chicago on Sale: Book 3 Nts in Oct Fr $370+/Nt
Save with Expedia, $185/night less
$84 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct at River Fr $84+/Nt
Save with Expedia, $9/night less
$127 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $127+/Nt
Expedia
$116 Chicago, Illinois Oct deal: Chicago Marriott at Medical District/UIC Fr $116+/Nt
Expedia
$328 Chicago, Illinois Book 5-Star Waldorf Astoria Chicago Fr $328+/Nt
Expedia
$115 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $115+/Nt
Expedia
$121 Chicago, Illinois Book 4-Star The Westin Michigan Avenue Chicago Fr $121+/Nt
Expedia
$96 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $96+/Nt
Expedia
$124 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $124+/Nt
Expedia
$133 Chicago, Illinois Book in Chicago: Save this Oct Fr $133+/Nt
Save with Expedia, $6/night less
$129 Chicago, Illinois Chicago Savings! Book at JW Marriott Chicago Fr $129+/Nt
Expedia
$153 Chicago, Illinois Chicago Savings! Book at W Chicago - City Center Fr $153+/Nt
Expedia
$159 Chicago, Illinois Book 3.5-Star Hilton Suites Chicago/Magnificent Mile Fr $159+/Nt
Expedia
$149 Chicago, Illinois Oct deal: Hyatt Chicago Magnificent Mile Fr $149+/Nt
Expedia
$113 Chicago, Illinois Book in Chicago: Save this Oct Fr $113+/Nt
Expedia
$166 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $166+/Nt
Expedia
$168 Chicago, Illinois Book 4-Star Swissotel Chicago Fr $168+/Nt
Save with Expedia, $42/night less
$93 Chicago, Illinois Chicago Savings! Book at Chicago's Essex Inn Fr $93+/Nt
Save with Expedia, $16/night less
$135 Chicago, Illinois Chicago Savings! Book at Holiday Inn Chicago O'Hare Fr $135+/Nt
Expedia
$69 Chicago, Illinois Book in Chicago: Save this Oct Fr $69+/Nt
Expedia
$103 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $103+/Nt
Expedia
$336 Chicago, Illinois The Ritz-Carlton Chicago (A Four Seasons ) in Oct: $336 & Up
Save with Expedia, $60/night less
$139 Chicago, Illinois Hilton Chicago O'Hare Airport in Oct: $139 & Up
Expedia
$127 Chicago, Illinois Oct deal: Burnham - a Kimpton Fr $127+/Nt
Save with Expedia, $22/night less
$159 Chicago, Illinois Chicago Savings! Book at Renaissance Chicago Fr $159+/Nt
Expedia
$79 Chicago, Illinois Book the Hyatt Regency McCormick Place 3 Nts in Oct Fr $79+/Nt
Expedia
$102 Chicago, Illinois Special deal: 4-Star Millennium Knickerbocker Chicago Fr $102+/Nt
Save with Expedia, $17/night less
$99 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $99+/Nt
Save with Expedia, $25/night less
$111 Chicago, Illinois Oct deal: Holiday Inn Chicago Downtown Fr $111+/Nt
Expedia
$82 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $82+/Nt
Save with Expedia, $20/night less
$136 Chicago, Illinois Chicago Marriott Downtown Magnificent Mile in Oct: $136 & Up
Expedia
$159 Chicago, Illinois Comfort Suites Michigan Avenue in Oct: $159 & Up
Expedia
$103 Addison, Illinois Save in Addison: Book 3 Nts in Oct Fr $103+/Nt
Expedia
$117 Addison, Illinois Addison Savings! Book at Hilton Garden Inn Addison Fr $117+/Nt
Expedia
$102 Alsip, Illinois Book the Doubletree Chicago / Alsip 3 Nts in Oct Fr $102+/Nt
Expedia
$69 Arlington Heights, Illinois Jameson Suites of Arlington Heights in Oct: $69 & Up
Save with Expedia, $23/night less
$128 Bedford Park, Illinois Hampton Inn Chicago-Midway Airport in Oct: $128 & Up
Expedia
$145 Bedford Park, Illinois Oct deal: Hilton Garden Inn Chicago Midway Airport Fr $145+/Nt
Expedia
$72 Bensenville, Illinois Save Big This Oct! Book 3 Nts in Bensenville Fr $72+/Nt
Expedia
$117 Bolingbrook, Illinois Save Big This Oct! Book 3 Nts at aloft Bolingbrook Fr $117+/Nt
Expedia
PRICEDESTINATIONDEAL
$149 New York City, New York Cheap Flights from Washington, DC
DealBase.com
$217 New York City, New York Cheap Flights from St. Louis
DealBase.com
$185 New York City, New York Cheap Flights from Miami
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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