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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$17 Chicago, Illinois Cheap Car Rentals in Chicago Fr $17/Day
CarRentals.com
$162 Chicago, Illinois Southwest Airlines Grab Your Favorite Seat Sale
DealBase.com
$149 Chicago, Illinois Hyatt Regency Chicago in Oct: $149 & Up
Expedia
$115 Chicago, Illinois Southwest Airlines Grab Your Favorite Seat Sale
DealBase.com
$115 Chicago, Illinois Special deal: 4-Star theWit - A DoubleTree by Hilton Fr $115+/Nt
Expedia
$134 Chicago, Illinois Southwest Airlines Grab Your Favorite Seat Sale
DealBase.com
$102 Chicago, Illinois Chicago Savings! Book at InterContinental Chicago Fr $102+/Nt
Expedia
$197 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$144 Chicago, Illinois Oct deal: Fairmont Chicago Millennium Park Fr $144+/Nt
Save with Expedia, $15/night less
$197 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$85 Chicago, Illinois Oct deal: Chicago's Essex Inn Fr $85+/Nt
Save with Expedia, $14/night less
$253 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$144 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct at The Silversmith Fr $144+/Nt
Save with Expedia, $25/night less
$169 Chicago, Illinois Southwest Airlines Grab Your Favorite Seat Sale
DealBase.com
$128 Chicago, Illinois Courtyard Chicago Downtown/Magnificent Mile in Oct: $128 & Up
Expedia
$267 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$109 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $109+/Nt
Expedia
$134 Chicago, Illinois Southwest Airlines Grab Your Favorite Seat Sale
DealBase.com
$129 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $129+/Nt
Expedia
$112 Chicago, Illinois Southwest Airlines Grab Your Favorite Seat Sale
DealBase.com
$128 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $128+/Nt
Expedia
$245 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$85 Chicago, Illinois Chicago Savings! Book at ACME Company Chicago Fr $85+/Nt
Save with Expedia, $14/night less
$133 Chicago, Illinois United Airlines US Fare Sale
DealBase.com
$113 Chicago, Illinois Hilton Chicago on Sale: Book 3 Nts in Oct Fr $113+/Nt
Expedia
$112+ Chicago, Illinois 4.5 Star Luxury Chicago Hotel on Sale! Starting from $112/nt
Jetsetter
$90 Chicago, Illinois Special deal: 3-Star Congress Plaza Fr $90+/Nt
Expedia
$85+ Chicago, Illinois 4-Star Chicago Hotels from $85
trivago
$136 Chicago, Illinois Book in Chicago: Save this Oct Fr $136+/Nt
Expedia
$125+ Chicago, Illinois Chicago on Sale! Starting From $125/nt
Jetsetter
$95 Chicago, Illinois Oct deal: Embassy Suites Chicago Downtown Fr $95+/Nt
Expedia
$522 Chicago, Illinois Great Rates in Chicago + Breakfast!
DealBase.com
$140 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $140+/Nt
Expedia
$156 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $156+/Nt
Expedia
$85 Chicago, Illinois Book 3-Star Hampton Inn & Suites Chicago - Downtown Fr $85+/Nt
Expedia
$129 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $129+/Nt
Expedia
$199 Chicago, Illinois Chicago Savings! Book at JW Marriott Chicago Fr $199+/Nt
Expedia
$150 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $150+/Nt
Expedia
$320 Chicago, Illinois Chicago Savings! Book at The Peninsula Chicago Fr $320+/Nt
Save with Expedia, $160/night less
$297 Chicago, Illinois Book in Chicago: Save this Oct Fr $297+/Nt
Save with Expedia, $98/night less
$147 Chicago, Illinois Book 4-Star Palomar Chicago, a Kimpton Fr $147+/Nt
Save with Expedia, $26/night less
$110 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $110+/Nt
Expedia
$108 Chicago, Illinois Save at 4-Star Raffaello: $108 & Up in Oct
Save with Expedia, $58/night less
$81 Chicago, Illinois Oct deal: Club Quarters Chicago - Central Loop Fr $81+/Nt
Save with Expedia, $8/night less
$108 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct at PUBLIC Chicago Fr $108+/Nt
Save with Expedia, $57/night less
$109 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $109+/Nt
Expedia
$129 Chicago, Illinois Book in Chicago: Save this Oct Fr $129+/Nt
Expedia
$70 Chicago, Illinois Oct deal: The Tremont Chicago at Magnificent Mile Fr $70+/Nt
Expedia
$103 Chicago, Illinois Book 3-Star Hampton Majestic Chicago Theatre District Fr $103+/Nt
Expedia
$299 Chicago, Illinois Waldorf Astoria Chicago in Oct: $299 & Up
Expedia
$153 Chicago, Illinois $153 & Up: The James Chicago 4.5-Star Hotel in Chicago
Save with Expedia, $26/night less
$130 Chicago, Illinois Book in Chicago: Save this Oct Fr $130+/Nt
Expedia
$166 Chicago, Illinois Chicago Savings! Book at Renaissance Chicago Fr $166+/Nt
Expedia
$127 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $127+/Nt
Save with Expedia, $22/night less
$109 Chicago, Illinois Book 3.5-Star Hilton Suites Chicago/Magnificent Mile Fr $109+/Nt
Expedia
$164 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $164+/Nt
Expedia
$153 Chicago, Illinois Oct deal: The Westin Chicago River North Fr $153+/Nt
Expedia
$159 Chicago, Illinois Small budget: Book dana and spa 3 Nts in Oct Fr $159+/Nt
Expedia
$79 Chicago, Illinois Chicago Savings! Book at Travelodge Chicago Downtown Fr $79+/Nt
Expedia
$122 Chicago, Illinois Chicago Savings! Book at Holiday Inn Chicago O'Hare Fr $122+/Nt
Expedia
$87 Chicago, Illinois Book 3.5-Star Indigo Chicago Downtown Gold Coast Fr $87+/Nt
Expedia
$68 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $68+/Nt
Expedia
$106 Chicago, Illinois Book in Chicago: Save at the Central Loop in Oct Fr $106+/Nt
Expedia
$103 Chicago, Illinois Book in Chicago: Save this Oct Fr $103+/Nt
Expedia
$207 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $207+/Nt
Expedia
$93 Chicago, Illinois Doubletree by Hilton Chicago Magnificent Mile in Oct: $93 & Up
Expedia
$169 Chicago, Illinois Oct deal: Conrad Chicago Fr $169+/Nt
Expedia
$110 Chicago, Illinois Book in Chicago: Save at the Hard Rock Chicago in Oct Fr $110+/Nt
Save with Expedia, $19/night less
$85 Chicago, Illinois Oct deal: Crowne Plaza Chicago Magnificent Mile Fr $85+/Nt
Expedia
$136 Chicago, Illinois Oct deal: Chicago Marriott Downtown Magnificent Mile Fr $136+/Nt
Expedia
$264 Chicago, Illinois Book 5-Star Four Seasons Chicago Fr $264+/Nt
Save with Expedia, $131/night less
$123 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $123+/Nt
Expedia
$96 Chicago, Illinois Chicago Savings! Book at BEST WESTERN Grant Park Fr $96+/Nt
Save with Expedia, $24/night less
$99 Chicago, Illinois Oct deal: Chicago South Loop Fr $99+/Nt
Expedia
$104 Chicago, Illinois Oct deal: Homewood Suites by Hilton Chicago Downtown Fr $104+/Nt
Expedia
$161 Chicago, Illinois Oct deal: The Blackstone A Renaissance Fr $161+/Nt
Expedia
$123 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $123+/Nt
Expedia
$260 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $260+/Nt
Expedia
$119 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $119+/Nt
Save with Expedia, $7/night less
$109 Chicago, Illinois Chicago Savings! Book at Holiday Inn Express Cass Fr $109+/Nt
Expedia
$99 Chicago, Illinois Special deal: 4-Star The Whitehall Fr $99+/Nt
Save with Expedia, $17/night less
$90 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $90+/Nt
Expedia
$99 Chicago, Illinois The Palmer House Hilton on Sale: Book 3 Nts in Oct Fr $99+/Nt
Expedia
$109 Chicago, Illinois Special deal: 3-Star Holiday Inn Chicago Downtown Fr $109+/Nt
Expedia
$110 Chicago, Illinois Book 4-Star Burnham - a Kimpton in Chicago Fr $110+/Nt
Save with Expedia, $19/night less
$139 Chicago, Illinois Book in Chicago: Save at the The Drake in Oct Fr $139+/Nt
Expedia
$168 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $168+/Nt
Save with Expedia, $42/night less
$140 Chicago, Illinois Book in Chicago: Save at the Days Inn Chicago in Oct Fr $140+/Nt
Expedia
$116 Chicago, Illinois Oct deal: Chicago Marriott at Medical District/UIC Fr $116+/Nt
Expedia
$116 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $116+/Nt
Save with Expedia, $21/night less
$126 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $126+/Nt
Expedia
$119 Chicago, Illinois Book in Chicago: Save this Oct Fr $119+/Nt
Expedia
$264 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $264+/Nt
Save with Expedia, $131/night less
$72 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $72+/Nt
Save with Expedia, $18/night less
$149 Chicago, Illinois Oct deal: Hyatt Chicago Magnificent Mile Fr $149+/Nt
Expedia
$102 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $102+/Nt
Save with Expedia, $17/night less
$161 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $161+/Nt
Save with Expedia, $69/night less
$109 Chicago, Illinois Embassy Suites Chicago Downtown Lakefront in Oct: $109 & Up
Expedia
$113 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $113+/Nt
Expedia
$137 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $137+/Nt
Save with Expedia, $46/night less
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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