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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$85+ Chicago, Illinois 4-Star Chicago Hotels from $85
trivago
$134 Chicago, Illinois Southwest Airlines Grab Your Favorite Seat Sale
DealBase.com
$13 Chicago, Illinois Cheap Car Rentals in Chicago Fr $13/Day
CarRentals.com
$112 Chicago, Illinois Southwest Airlines Grab Your Favorite Seat Sale
DealBase.com
$17 Chicago, Illinois Cheap Car Rentals in Chicago Fr $17/Day
CarRentals.com
$133 Chicago, Illinois United Airlines US Fare Sale
DealBase.com
$102 Chicago, Illinois Book 4.5-Star InterContinental Chicago Fr $102+/Nt
Expedia
$197 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$112+ Chicago, Illinois 4.5 Star Luxury Chicago Hotel on Sale! Starting from $112/nt
Jetsetter
$115 Chicago, Illinois Southwest Airlines Grab Your Favorite Seat Sale
DealBase.com
$95 Chicago, Illinois Book 4-Star Hilton Chicago Fr $95+/Nt
Expedia
$169 Chicago, Illinois Southwest Airlines Grab Your Favorite Seat Sale
DealBase.com
$103 Chicago, Illinois Book 3-Star Hampton Majestic Chicago Theatre District Fr $103+/Nt
Expedia
$162 Chicago, Illinois Southwest Airlines Grab Your Favorite Seat Sale
DealBase.com
$209 Chicago, Illinois Book in Chicago: Save at the Conrad Chicago in Nov Fr $209+/Nt
Expedia
$245 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$45 Chicago, Illinois Book 3 Nts in Chicago this Nov Fr $45+/Nt
Save with Expedia, $30/night less
$253 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$91 Chicago, Illinois Book 4-Star Warwick Allerton Chicago in Chicago Fr $91+/Nt
Save with Expedia, $73/night less
$134 Chicago, Illinois Southwest Airlines Grab Your Favorite Seat Sale
DealBase.com
$139 Chicago, Illinois Nov deal: Kinzie Fr $139+/Nt
Expedia
$125+ Chicago, Illinois Chicago on Sale! Starting From $125/nt
Jetsetter
$102 Chicago, Illinois Book in Chicago: Save this Nov Fr $102+/Nt
Save with Expedia, $34/night less
$270 Chicago, Illinois US Airways Domestic e-Saver Specials for 11/1/14
DealBase.com
$110 Chicago, Illinois Chicago Savings! Book 3 Nts in Nov Fr $110+/Nt
Expedia
$124 Chicago, Illinois Book the Holiday Inn Chicago O'Hare 3 Nts in Nov Fr $124+/Nt
Expedia
$129 Chicago, Illinois Chicago Savings! Book at Days Inn Chicago Fr $129+/Nt
Expedia
$109 Chicago, Illinois Book 4-Star MileNorth, A Chicago in Chicago Fr $109+/Nt
Expedia
$101 Chicago, Illinois Book the Holiday Inn Chicago Downtown 3 Nts in Nov Fr $101+/Nt
Expedia
$274 Chicago, Illinois Book 5-Star Park Hyatt Chicago in Chicago Fr $274+/Nt
Expedia
$857 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $857
Expedia
$534 Chicago, Illinois 3.5-Star Chicago Sale! 3 Nts + Air Fr $534
Expedia
$97 Chicago, Illinois Chicago Savings! Book 3 Nts in Nov Fr $97+/Nt
Expedia
$116 Chicago, Illinois Chicago Marriott at Medical District/UIC in Nov: $116 & Up
Expedia
$297 Chicago, Illinois Book 3 Nts in Chicago this Nov Fr $297+/Nt
Save with Expedia, $98/night less
$99 Chicago, Illinois Book in Chicago: Save this Nov Fr $99+/Nt
Expedia
$125 Chicago, Illinois Nov deal: Indigo Chicago Downtown Gold Coast Fr $125+/Nt
Expedia
$99 Chicago, Illinois Small budget: Stay in Chicago this Nov Fr $99+/Nt
Expedia
$134 Chicago, Illinois Chicago Savings! Book at The Blackstone A Renaissance Fr $134+/Nt
Expedia
$136 Chicago, Illinois Nov deal: Chicago Marriott Downtown Magnificent Mile Fr $136+/Nt
Expedia
$109 Chicago, Illinois Save in Chicago: Book 3 Nts in Nov Fr $109+/Nt
Expedia
$129 Chicago, Illinois Chicago Savings! Book 3 Nts in Nov Fr $129+/Nt
Expedia
$151 Chicago, Illinois Chicago Savings! Book at Sofitel Chicago Water Tower Fr $151+/Nt
Expedia
$104 Chicago, Illinois Hilton Suites Chicago/Magnificent Mile in Nov: $104 & Up
Expedia
$99 Chicago, Illinois Save Big This Nov! Book 3 Nts at Blake Chicago Fr $99+/Nt
Expedia
$111 Chicago, Illinois Chicago Savings! Book 3 Nts in Nov Fr $111+/Nt
Expedia
$99 Chicago, Illinois Book 3 Nts in Chicago this Nov Fr $99+/Nt
Expedia
$110 Chicago, Illinois Hyatt Chicago Magnificent Mile in Nov: $110 & Up
Expedia
$133 Chicago, Illinois The Westin Michigan Avenue Chicago in Nov: $133 & Up
Expedia
$109 Chicago, Illinois Chicago Savings! Book 3 Nts in Nov Fr $109+/Nt
Save with Expedia, $7/night less
$109 Chicago, Illinois Chicago Savings! Book at Holiday Inn Express Cass Fr $109+/Nt
Expedia
$421 Chicago, Illinois Chicago 3.5-Star Hotel Sale! 3 Nts + Air Fr $421
Expedia
$278 Chicago, Illinois Save Big This Nov! Book 3 Nts in Chicago Fr $278+/Nt
Expedia
$144 Chicago, Illinois Book the The Silversmith 3 Nts in Nov Fr $144+/Nt
Save with Expedia, $25/night less
$127 Chicago, Illinois Book 3.5-Star Wyndham Grand Chicago Riverfront Fr $127+/Nt
Save with Expedia, $22/night less
$153 Chicago, Illinois The James Chicago on Sale: Book 3 Nts in Nov Fr $153+/Nt
Save with Expedia, $26/night less
$109 Chicago, Illinois $109 & Up: Sheraton Chicago and Towers 4-Star Hotel in Chicago
Expedia
$108 Chicago, Illinois Book in Chicago: Save this Nov Fr $108+/Nt
Save with Expedia, $58/night less
$115 Chicago, Illinois Save Big This Nov! Book 3 Nts in Chicago Fr $115+/Nt
Expedia
$897 Chicago, Illinois Save at 5-Star Hotel: 3 Nts + Air to Chicago Fr $897
Expedia
$85 Chicago, Illinois Small budget: Stay in Chicago this Nov Fr $85+/Nt
Expedia
$68 Chicago, Illinois Book in Chicago: Save this Nov Fr $68+/Nt
Save with Expedia, $17/night less
$317 Chicago, Illinois Book 3 Nts in Chicago this Nov Fr $317+/Nt
Save with Expedia, $158/night less
$93 Chicago, Illinois Book in Chicago: Save this Nov Fr $93+/Nt
Expedia
$119 Chicago, Illinois Book 3.5-Star Crowne Plaza Chicago - The Metro Fr $119+/Nt
Save with Expedia, $7/night less
$96 Chicago, Illinois Save in Chicago: Book 3 Nts in Nov Fr $96+/Nt
Save with Expedia, $10/night less
$110 Chicago, Illinois Chicago Savings! Book 3 Nts in Nov Fr $110+/Nt
Expedia
$99 Chicago, Illinois Homewood Suites by Hilton Chicago Downtown in Nov: $99 & Up
Expedia
$264 Chicago, Illinois Book 5-Star Four Seasons Chicago Fr $264+/Nt
Save with Expedia, $131/night less
$149 Chicago, Illinois Chicago Savings! Book at JW Marriott Chicago Fr $149+/Nt
Expedia
$133 Chicago, Illinois Save at 3.5-Star Buckingham Athletic Club: $133 & Up in Nov
Expedia
$94 Chicago, Illinois $94 & Up: Hyatt Regency Chicago 4-Star Hotel in Chicago
Expedia
$127 Chicago, Illinois Small budget: Stay in Chicago this Nov Fr $127+/Nt
Expedia
$112 Chicago, Illinois Chicago Savings! Book at Radisson Blu Aqua Fr $112+/Nt
Expedia
$93 Chicago, Illinois Book 3 Nts in Chicago this Nov Fr $93+/Nt
Expedia
$80 Chicago, Illinois Book 3-Star Congress Plaza Fr $80+/Nt
Expedia
$894 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $894
Expedia
$119 Chicago, Illinois Special deal: 4-Star W Chicago Lakeshore Fr $119+/Nt
Expedia
$2,210 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $2,210
Expedia
$69 Chicago, Illinois Chicago Savings! Book at BEST WESTERN Grant Park Fr $69+/Nt
Save with Expedia, $17/night less
$90 Chicago, Illinois Book 3-Star BEST WESTERN River North Fr $90+/Nt
Expedia
$140 Chicago, Illinois Monaco Chicago - a Kimpton in Nov: $140 & Up
Save with Expedia, $59/night less
$70 Chicago, Illinois Book 3-Star The Tremont Chicago at Magnificent Mile Fr $70+/Nt
Expedia
$90 Chicago, Illinois Small budget: Stay in Chicago this Nov Fr $90+/Nt
Expedia
$136 Chicago, Illinois Chicago Savings! Book 3 Nts in Nov at dana and spa Fr $136+/Nt
Expedia
$85 Chicago, Illinois $85 & Up: ACME Company Chicago 3-Star Hotel in Chicago
Save with Expedia, $14/night less
$127 Chicago, Illinois Small budget: Book Burnham - a Kimpton 3 Nts in Nov Fr $127+/Nt
Save with Expedia, $22/night less
$114 Chicago, Illinois Save Big This Nov! Book 3 Nts in Chicago Fr $114+/Nt
Expedia
$110 Chicago, Illinois Save Big This Nov! Book 3 Nts at Hard Rock Chicago Fr $110+/Nt
Save with Expedia, $19/night less
$128 Chicago, Illinois Book 4.5-Star Omni Chicago in Chicago Fr $128+/Nt
Save with Expedia, $31/night less
$119 Chicago, Illinois Book 4-Star The Drake Fr $119+/Nt
Expedia
$85 Chicago, Illinois $85 & Up: Chicago's Essex Inn 3-Star Hotel in Chicago
Save with Expedia, $14/night less
$109 Chicago, Illinois Book 3 Nts in Chicago this Nov Fr $109+/Nt
Expedia
$119 Chicago, Illinois Book 4-Star Palomar Chicago, a Kimpton Fr $119+/Nt
Save with Expedia, $20/night less
$159 Chicago, Illinois Chicago Savings! Book 3 Nts in Nov Fr $159+/Nt
Expedia
$89 Chicago, Illinois Save Big This Nov! Book 3 Nts in Chicago Fr $89+/Nt
Expedia
$128 Chicago, Illinois Save at 4-Star Swissotel Chicago: $128 & Up in Nov
Save with Expedia, $32/night less
$249 Chicago, Illinois Book 3 Nts in Chicago this Nov Fr $249+/Nt
Expedia
$144 Chicago, Illinois Save in Chicago: Book 3 Nts in Nov Fr $144+/Nt
Save with Expedia, $15/night less
$68 Chicago, Illinois Chicago Savings! Book at Travelodge Chicago Downtown Fr $68+/Nt
Expedia
PRICEDESTINATIONDEAL
$220 Newark, New Jersey Cheap Flights from Charlotte
DealBase.com
$337 Newark, New Jersey Cheap Flights from Los Angeles
DealBase.com
$201 Newark, New Jersey Cheap Flights from Nashville
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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