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Chicago, IL Hotel Deals

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Chicago, IL Hotel Deals

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TYPE PRICE DESTINATION DEAL
$99+ Chicago, Illinois Save Up To 25% on 4-Star Chicago Hotels
trivago
$374 Chicago, Illinois Save Big This Oct! Book 3 Nts at Four Seasons Chicago Fr $374+/Nt
Save with Expedia, $41/night less
$112+ Chicago, Illinois 4.5 Star Luxury Chicago Hotel on Sale! Starting from $112/nt
Jetsetter
$394 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $394+/Nt
Save with Expedia, $98/night less
$125+ Chicago, Illinois Chicago on Sale! Starting From $125/nt
Jetsetter
$203 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $203+/Nt
Expedia
$522 Chicago, Illinois Great Rates in Chicago + Breakfast!
DealBase.com
$139 Chicago, Illinois Book in Chicago: Save this Oct Fr $139+/Nt
Expedia
$146 Chicago, Illinois Special deal: 4-Star Hilton Chicago O'Hare Airport Fr $146+/Nt
Expedia
$226 Chicago, Illinois Special deal: 4-Star Radisson Blu Aqua Fr $226+/Nt
Expedia
$170 Chicago, Illinois Book in Chicago: Save this Oct Fr $170+/Nt
Save with Expedia, $29/night less
$246 Chicago, Illinois Oct deal: Millennium Knickerbocker Chicago Fr $246+/Nt
Save with Expedia, $43/night less
$153 Chicago, Illinois Book the Blake Chicago 3 Nts in Oct Fr $153+/Nt
Expedia
$206 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $206+/Nt
Expedia
$179 Chicago, Illinois Book in Chicago: Save this Oct Fr $179+/Nt
Expedia
$168 Chicago, Illinois Book in Chicago: Save this Oct Fr $168+/Nt
Save with Expedia, $11/night less
$141 Chicago, Illinois Book 3.5-Star Club Quarters Chicago - Central Loop Fr $141+/Nt
Expedia
$161 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $161+/Nt
Expedia
$189 Chicago, Illinois Save Big This Oct! Book 3 Nts at Felix Fr $189+/Nt
Save with Expedia, $34/night less
$195 Chicago, Illinois $195 & Up: PUBLIC Chicago 4-Star Hotel in Chicago
Expedia
$229 Chicago, Illinois Book 4-Star The Drake in Chicago Fr $229+/Nt
Expedia
$213 Chicago, Illinois Hampton Majestic Chicago Theatre District in Oct: $213 & Up
Expedia
$110 Chicago, Illinois BEST WESTERN Grant Park in Oct: $110 & Up
Save with Expedia, $27/night less
$199 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $199+/Nt
Expedia
$179 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $179+/Nt
Expedia
$197 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $197+/Nt
Expedia
$181 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $181+/Nt
Save with Expedia, $32/night less
$129 Chicago, Illinois Book the Hyatt Regency McCormick Place 3 Nts in Oct Fr $129+/Nt
Expedia
$269 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $269+/Nt
Expedia
$221 Chicago, Illinois Sofitel Chicago Water Tower in Oct: $221 & Up
Expedia
$228 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $228+/Nt
Expedia
$194 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $194+/Nt
Expedia
$135 Chicago, Illinois Congress Plaza on Sale: Book 3 Nts in Oct Fr $135+/Nt
Expedia
$296 Chicago, Illinois Book 4-Star The Westin Chicago River North in Chicago Fr $296+/Nt
Expedia
$210 Chicago, Illinois Courtyard Chicago Downtown/Magnificent Mile in Oct: $210 & Up
Expedia
$466 Chicago, Illinois Small budget: Book The Peninsula Chicago 3 Nts in Oct Fr $466+/Nt
Expedia
$141 Chicago, Illinois Book in Chicago: Save this Oct Fr $141+/Nt
Expedia
$239 Chicago, Illinois The Blackstone A Renaissance in Oct: $239 & Up
Expedia
$179 Chicago, Illinois Homewood Suites by Hilton Chicago Downtown in Oct: $179 & Up
Expedia
$203 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $203+/Nt
Expedia
$248 Chicago, Illinois Chicago Savings! Book at InterContinental Chicago Fr $248+/Nt
Expedia
$169 Chicago, Illinois Chicago Savings! Book at Buckingham Athletic Club Fr $169+/Nt
Expedia
$250 Chicago, Illinois Oct deal: Sheraton Chicago and Towers Fr $250+/Nt
Expedia
$239 Chicago, Illinois Oct deal: JW Marriott Chicago Fr $239+/Nt
Expedia
$269 Chicago, Illinois Fairmont Chicago Millennium Park in Oct: $269 & Up
Expedia
$164 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $164+/Nt
Expedia
$235 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $235+/Nt
Save with Expedia, $101/night less
$263 Chicago, Illinois Oct deal: Wyndham Grand Chicago Riverfront Fr $263+/Nt
Save with Expedia, $46/night less
$199 Chicago, Illinois Save at 4-Star MileNorth, A Chicago: $199 & Up in Oct
Expedia
$193 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $193+/Nt
Expedia
$103 Chicago, Illinois Hostelling International Chicago in Oct: $103 & Up
Expedia
$178 Chicago, Illinois Oct deal: Crowne Plaza Chicago Magnificent Mile Fr $178+/Nt
Expedia
$156 Chicago, Illinois Book 3-Star Holiday Inn Express Cass in Chicago Fr $156+/Nt
Expedia
$207 Chicago, Illinois Chicago Savings! Book at ACME Company Chicago Fr $207+/Nt
Save with Expedia, $9/night less
$134 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct at Central Loop Fr $134+/Nt
Save with Expedia, $9/night less
$183 Chicago, Illinois Oct deal: La Quinta Inn & Suites Chicago Downtown Fr $183+/Nt
Expedia
$270 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $270+/Nt
Expedia
$136 Chicago, Illinois Red Roof Inn Chicago Downtown Magnificent Mile in Oct: $136 & Up
Save with Expedia, $34/night less
$259 Chicago, Illinois Oct deal: Hyatt Chicago Magnificent Mile Fr $259+/Nt
Expedia
$167 Chicago, Illinois Oct deal: BEST WESTERN River North Fr $167+/Nt
Expedia
$415 Chicago, Illinois Oct deal: The Ritz-Carlton Chicago (A Four Seasons ) Fr $415+/Nt
Expedia
$193 Chicago, Illinois Save at 3.5-Star Kinzie: $193 & Up in Oct
Expedia
$128 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $128+/Nt
Save with Expedia, $87/night less
$224 Chicago, Illinois Residence Inn Chicago Downtown / River North in Oct: $224 & Up
Expedia
$193 Chicago, Illinois Book the dana and spa 3 Nts in Oct Fr $193+/Nt
Expedia
$199 Chicago, Illinois Book the Comfort Suites Michigan Avenue 3 Nts in Oct Fr $199+/Nt
Expedia
$176 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $176+/Nt
Save with Expedia, $43/night less
$193 Chicago, Illinois Holiday Inn Chicago Mart Plaza River North in Oct: $193 & Up
Expedia
$249 Chicago, Illinois Embassy Suites Chicago Downtown Lakefront in Oct: $249 & Up
Expedia
$130 Chicago, Illinois Oct deal: Indigo Chicago Downtown Gold Coast Fr $130+/Nt
Expedia
$119 Chicago, Illinois Travelodge Chicago Downtown in Oct: $119 & Up
Expedia
$150 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $150+/Nt
Expedia
$159 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct at Conrad Chicago Fr $159+/Nt
Expedia
$259 Chicago, Illinois Oct deal: Chicago Marriott Downtown Magnificent Mile Fr $259+/Nt
Expedia
$198 Chicago, Illinois Hard Rock Chicago on Sale: Book 3 Nts in Oct Fr $198+/Nt
Save with Expedia, $35/night less
$247 Chicago, Illinois Book in Chicago: Save this Oct Fr $247+/Nt
Expedia
$119 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $119+/Nt
Expedia
$383 Chicago, Illinois Save at 5-Star Waldorf Astoria Chicago: $383 & Up in Oct
Expedia
$112 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $112+/Nt
Expedia
$249 Chicago, Illinois Special deal: 4-Star Swissotel Chicago Fr $249+/Nt
Save with Expedia, $28/night less
$169 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $169+/Nt
Expedia
$275 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $275+/Nt
Expedia
$170 Chicago, Illinois Small budget: Book Raffaello 3 Nts in Oct Fr $170+/Nt
Save with Expedia, $91/night less
$163 Chicago, Illinois Chicago Savings! Book at The Palmer House Hilton Fr $163+/Nt
Expedia
$218 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $218+/Nt
Expedia
$152 Chicago, Illinois Book 4-Star The Whitehall Fr $152+/Nt
Save with Expedia, $37/night less
$353 Chicago, Illinois Book the Park Hyatt Chicago 3 Nts in Oct Fr $353+/Nt
Expedia
$189 Chicago, Illinois Book the Allegro Chicago - a Kimpton 3 Nts in Oct Fr $189+/Nt
Expedia
$235 Chicago, Illinois Book in Chicago: Save at the The James Chicago in Oct Fr $235+/Nt
Save with Expedia, $41/night less
$152 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $152+/Nt
Save with Expedia, $37/night less
$133 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $133+/Nt
Save with Expedia, $23/night less
$117 Alsip, Illinois Oct deal: Doubletree Chicago / Alsip Fr $117+/Nt
Expedia
$114 Schiller Park, Illinois Save in Schiller Park: Book 3 Nts in Oct Fr $114+/Nt
Save with Expedia, $6/night less
$97 Tinley Park, Illinois Hampton Inn Chicago / Tinley Park in Oct: $97 & Up
Expedia
$117 Tinley Park, Illinois Oct deal: Hilton Garden Inn Chicago/Tinley Park Fr $117+/Nt
Expedia
$112 Rosemont, Illinois Book 4-Star Hyatt Regency O'Hare Fr $112+/Nt
Expedia
$99 Northbrook, Illinois Oct deal: Hilton Northbrook Fr $99+/Nt
Expedia
$81 Addison, Illinois Book 3 Nts in Addison this Oct Fr $81+/Nt
Expedia
$183 Lombard, Illinois Embassy Suites Chicago - Lombard / Oak Brook in Oct: $183 & Up
Expedia
$89 Oakbrook Terrace, Illinois Book 3-Star Hilton Garden Inn Oakbrook Terrace Fr $89+/Nt
Expedia
PRICEDESTINATIONDEAL
$145 New York City, New York Cheap Flights from Washington, DC
DealBase.com
$193 New York City, New York Cheap Flights from Charlotte
DealBase.com
$215 New York City, New York Cheap Flights from Milwaukee
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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