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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$960 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $960
Expedia
$34 Chicago, Illinois Spirit Airlines Minneapolis Specials
DealBase.com
$81 Chicago, Illinois Book 3-Star Homewood Suites by Hilton Chicago Downtown Fr $81+/Nt
Expedia
$128 Chicago, Illinois Southwest Airlines Early Black Friday Savings
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$91 Chicago, Illinois Chicago Savings! Book 3 Nts in Nov Fr $91+/Nt
Save with Expedia, $38/night less
$23 Chicago, Illinois Spirit Airlines Spirit Day Deals
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$3,379 Chicago, Illinois Chicago 3.5-Star Hotel Sale! 3 Nts + Air Fr $3,379
Expedia
$179 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$100 Chicago, Illinois Nov deal: Indigo Chicago Downtown Gold Coast Fr $100+/Nt
Expedia
$53 Chicago, Illinois Spirit Airlines Spirit Day Deals
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$76 Chicago, Illinois Small budget: Book ACME Company Chicago 3 Nts in Nov Fr $76+/Nt
Save with Expedia, $13/night less
$112 Chicago, Illinois Southwest Airlines Early Black Friday Savings
DealBase.com
$552 Chicago, Illinois Save at 3.5-Star Hotel: 3 Nts + Air to Chicago Fr $552
Expedia
$112+ Chicago, Illinois 4.5 Star Luxury Chicago Hotel on Sale! Starting from $112/nt
Jetsetter
$547 Chicago, Illinois Chicago 4.5-Star Hotel Sale! 3 Nts + Air Fr $547
Expedia
$73 Chicago, Illinois Spirit Airlines Spirit Day Deals
DealBase.com
$85 Chicago, Illinois Book 3-Star Hampton Inn & Suites Chicago - Downtown Fr $85+/Nt
Expedia
$88 Chicago, Illinois Exclusive! 40% Off + Free Breakfast!
BookIt.com
$76 Chicago, Illinois Nov deal: Crowne Plaza Chicago Magnificent Mile Fr $76+/Nt
Expedia
$83 Chicago, Illinois Spirit Airlines Spirit Day Deals
DealBase.com
$107 Chicago, Illinois Save Big This Nov! Book 3 Nts in Chicago Fr $107+/Nt
Expedia
$169 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$81 Chicago, Illinois Save Big This Nov! Book 3 Nts in Chicago at River Fr $81+/Nt
Save with Expedia, $8/night less
$23 Chicago, Illinois Spirit Airlines Spirit Day Deals
DealBase.com
$120 Chicago, Illinois Chicago Savings! Book 3 Nts in Nov Fr $120+/Nt
Save with Expedia, $30/night less
$200 Chicago, Illinois Virgin America Current Lowest Fares
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$111 Chicago, Illinois Save Big This Nov! Book 3 Nts in Chicago Fr $111+/Nt
Expedia
$200 Chicago, Illinois Virgin America Current Lowest Fares
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$127 Chicago, Illinois Hard Rock Chicago in Nov: $127 & Up
Save with Expedia, $22/night less
$131 Chicago, Illinois Southwest Airlines Early Black Friday Savings
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$83 Chicago, Illinois Chicago Savings! Book at BEST WESTERN Grant Park Fr $83+/Nt
Expedia
$63 Chicago, Illinois Spirit Airlines Spirit Day Deals
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$83 Chicago, Illinois Nov deal: Holiday Inn Chicago Mart Plaza River North Fr $83+/Nt
Expedia
$63 Chicago, Illinois Spirit Airlines Spirit Day Deals
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$94 Chicago, Illinois Hilton Suites Chicago/Magnificent Mile in Nov: $94 & Up
Expedia
$53 Chicago, Illinois Spirit Airlines Spirit Day Deals
DealBase.com
$86 Chicago, Illinois Book 4-Star Hilton Chicago O'Hare Airport Fr $86+/Nt
Expedia
$38 Chicago, Illinois Spirit Airlines Spirit Day Deals
DealBase.com
$129 Chicago, Illinois Book in Chicago: Save this Nov Fr $129+/Nt
Expedia
$68 Chicago, Illinois Spirit Airlines Spirit Day Deals
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$109 Chicago, Illinois Nov deal: Allegro Chicago - a Kimpton Fr $109+/Nt
Expedia
$63 Chicago, Illinois Spirit Airlines Spirit Day Deals
DealBase.com
$132 Chicago, Illinois Book in Chicago: Save at the PUBLIC Chicago in Nov Fr $132+/Nt
Expedia
$85+ Chicago, Illinois 4-Star Chicago Hotels from $85
trivago
$76 Chicago, Illinois Nov deal: The Tremont Chicago at Magnificent Mile Fr $76+/Nt
Expedia
$125+ Chicago, Illinois Chicago on Sale! Starting From $125/nt
Jetsetter
$97 Chicago, Illinois Book in Chicago: Save this Nov Fr $97+/Nt
Expedia
$23 Chicago, Illinois Spirit Airlines Spirit Day Deals
DealBase.com
$64 Chicago, Illinois Save Big This Nov! Book 3 Nts in Chicago Fr $64+/Nt
Expedia
$200 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$125 Chicago, Illinois Chicago Marriott at Medical District/UIC in Nov: $125 & Up
Expedia
$53 Chicago, Illinois Spirit Airlines Spirit Day Deals
DealBase.com
$1,629 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $1,629
Expedia
$130 Chicago, Illinois Southwest Airlines Early Black Friday Savings
DealBase.com
$119 Chicago, Illinois Chicago Savings! Book 3 Nts in Nov Fr $119+/Nt
Expedia
$38 Chicago, Illinois Spirit Airlines Spirit Day Deals
DealBase.com
$85 Chicago, Illinois Chicago Savings! Book 3 Nts in Nov Fr $85+/Nt
Expedia
$79 Chicago, Illinois Sun Country Airlines Fares to be Thankful For
DealBase.com
$84 Chicago, Illinois Book 3 Nts in Chicago this Nov Fr $84+/Nt
Save with Expedia, $9/night less
$121 Chicago, Illinois Southwest Airlines Early Black Friday Savings
DealBase.com
$133 Chicago, Illinois Book in Chicago: Save at the Raffaello in Nov Fr $133+/Nt
Save with Expedia, $71/night less
$200 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$79 Chicago, Illinois Save Big This Nov! Book 3 Nts in Chicago Fr $79+/Nt
Expedia
$88 Chicago, Illinois Spirit Airlines Spirit Day Deals
DealBase.com
$100 Chicago, Illinois Book the Sheraton Chicago and Towers 3 Nts in Nov Fr $100+/Nt
Expedia
$38 Chicago, Illinois Spirit Airlines Spirit Day Deals
DealBase.com
$555 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $555
Expedia
$48 Chicago, Illinois Spirit Airlines Spirit Day Deals
DealBase.com
$68 Chicago, Illinois Small budget: Stay in Chicago this Nov Fr $68+/Nt
Expedia
$230 Chicago, Illinois Book 3 Nts in Chicago this Nov Fr $230+/Nt
Expedia
$437 Chicago, Illinois 3.5-Star Chicago Sale! 3 Nts + Air Fr $437
Expedia
$99 Chicago, Illinois Book in Chicago: Save at the Chicago South Loop in Nov Fr $99+/Nt
Expedia
$89 Chicago, Illinois Chicago Savings! Book at The Palmer House Hilton Fr $89+/Nt
Expedia
$80 Chicago, Illinois Book 3 Nts in Chicago this Nov Fr $80+/Nt
Save with Expedia, $19/night less
$89 Chicago, Illinois Chicago Savings! Book 3 Nts in Nov at The Whitehall Fr $89+/Nt
Expedia
$304 Chicago, Illinois Chicago Savings! Book at Waldorf Astoria Chicago Fr $304+/Nt
Expedia
$96 Chicago, Illinois $96 & Up: Comfort Suites Michigan Avenue 3-Star Hotel in Chicago
Expedia
$109 Chicago, Illinois dana and spa on Sale: Book 3 Nts in Nov Fr $109+/Nt
Expedia
$120 Chicago, Illinois Save in Chicago: Book 3 Nts in Nov Fr $120+/Nt
Expedia
$110 Chicago, Illinois Chicago Savings! Book at Buckingham Athletic Club Fr $110+/Nt
Save with Expedia, $19/night less
$136 Chicago, Illinois Save at 4-Star Fairmont Chicago Millennium Park: $136 & Up in Nov
Save with Expedia, $23/night less
$991 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $991
Expedia
$85 Chicago, Illinois Book 4-Star Hilton Chicago Fr $85+/Nt
Expedia
$144 Chicago, Illinois $144 & Up: The James Chicago 4.5-Star Hotel in Chicago
Save with Expedia, $25/night less
$129 Chicago, Illinois JW Marriott Chicago on Sale: Book 3 Nts in Nov Fr $129+/Nt
Expedia
$96 Chicago, Illinois Chicago Savings! Book at W Chicago Lakeshore Fr $96+/Nt
Expedia
$81 Chicago, Illinois Save Big This Nov! Book 3 Nts at Central Loop Fr $81+/Nt
Save with Expedia, $8/night less
$115 Chicago, Illinois Nov deal: theWit - A DoubleTree by Hilton Fr $115+/Nt
Expedia
$93 Chicago, Illinois Save in Chicago: Book 3 Nts in Nov Fr $93+/Nt
Expedia
$159 Chicago, Illinois Book the Renaissance Chicago 3 Nts in Nov Fr $159+/Nt
Expedia
$109 Chicago, Illinois Book 4.5-Star InterContinental Chicago in Chicago Fr $109+/Nt
Expedia
$119 Chicago, Illinois Chicago Savings! Book at W Chicago - City Center Fr $119+/Nt
Expedia
$264 Chicago, Illinois Small budget: Stay in Chicago this Nov Fr $264+/Nt
Save with Expedia, $131/night less
$90 Chicago, Illinois Save at 3.5-Star Embassy Suites Chicago Downtown: $90 & Up in Nov
Expedia
$91 Chicago, Illinois Save at 4-Star Hyatt Regency Chicago: $91 & Up in Nov
Save with Expedia, $38/night less
$119 Chicago, Illinois Save Big This Nov! Book 3 Nts in Chicago Fr $119+/Nt
Expedia
$209 Chicago, Illinois Chicago Savings! Book 3 Nts in Nov at Majestic Fr $209+/Nt
Expedia
$109 Chicago, Illinois Save in Chicago: Book 3 Nts in Nov Fr $109+/Nt
Expedia
$264 Chicago, Illinois The Ritz-Carlton Chicago (A Four Seasons ) in Nov: $264 & Up
Save with Expedia, $131/night less
$131 Chicago, Illinois Chicago Savings! Book 3 Nts in Nov Fr $131+/Nt
Expedia
PRICEDESTINATIONDEAL
$283 Newark, New Jersey Cheap Flights from Phoenix
DealBase.com
$219 Newark, New Jersey Cheap Flights from Milwaukee
DealBase.com
$328 Newark, New Jersey Cheap Flights from San Francisco
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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