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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
$244 Chicago, Illinois Book 5-Star Park Hyatt Chicago Fr $244+/Nt
Expedia
$107 Chicago, Illinois Last Minute Over 30% Off + Breakfast
BookIt.com
$99 Chicago, Illinois Hyatt Regency Chicago on Sale: Book 3 Nts in Nov Fr $99+/Nt
Expedia
$130 Chicago, Illinois Southwest Airlines Early Black Friday Savings
DealBase.com
$99 Chicago, Illinois Book in Chicago: Save at the Chicago South Loop in Nov Fr $99+/Nt
Expedia
$121 Chicago, Illinois Southwest Airlines Early Black Friday Savings
DealBase.com
$104 Chicago, Illinois $104 & Up: The Silversmith 3.5-Star Hotel in Chicago
Save with Expedia, $19/night less
$112 Chicago, Illinois Southwest Airlines Early Black Friday Savings
DealBase.com
$113 Chicago, Illinois Buckingham Athletic Club on Sale: Book 3 Nts in Nov Fr $113+/Nt
Save with Expedia, $20/night less
$131 Chicago, Illinois Southwest Airlines Early Black Friday Savings
DealBase.com
$84 Chicago, Illinois Small budget: Stay in Chicago this Nov Fr $84+/Nt
Expedia
$79 Chicago, Illinois Sun Country Airlines Fares to be Thankful For
DealBase.com
$85 Chicago, Illinois Small budget: Stay in Chicago this Nov Fr $85+/Nt
Expedia
$128 Chicago, Illinois Southwest Airlines Early Black Friday Savings
DealBase.com
$99 Chicago, Illinois Book 3-Star Comfort Suites Michigan Avenue in Chicago Fr $99+/Nt
Expedia
$112+ Chicago, Illinois 4.5 Star Luxury Chicago Hotel on Sale! Starting from $112/nt
Jetsetter
$149 Chicago, Illinois $149 & Up: JW Marriott Chicago 4-Star Hotel in Chicago
Expedia
$125+ Chicago, Illinois Chicago on Sale! Starting From $125/nt
Jetsetter
$81 Chicago, Illinois River on Sale: Book 3 Nts in Nov Fr $81+/Nt
Save with Expedia, $8/night less
$90 Chicago, Illinois Book in Chicago: Save at the The Whitehall in Nov Fr $90+/Nt
Save with Expedia, $23/night less
$129 Chicago, Illinois Book 3 Nts in Chicago this Nov Fr $129+/Nt
Expedia
$99 Chicago, Illinois Embassy Suites Chicago Downtown in Nov: $99 & Up
Expedia
$120 Chicago, Illinois Book 3 Nts in Chicago this Nov Fr $120+/Nt
Expedia
$80 Chicago, Illinois Small budget: Stay in Chicago this Nov Fr $80+/Nt
Expedia
$111 Chicago, Illinois Book 4-Star PUBLIC Chicago Fr $111+/Nt
Expedia
$93 Chicago, Illinois Book 4-Star Hilton Chicago O'Hare Airport Fr $93+/Nt
Expedia
$95 Chicago, Illinois La Quinta Inn & Suites Chicago Downtown in Nov: $95 & Up
Expedia
$109 Chicago, Illinois dana and spa on Sale: Book 3 Nts in Nov Fr $109+/Nt
Expedia
$100 Chicago, Illinois Special deal: 4-Star Sheraton Chicago and Towers Fr $100+/Nt
Expedia
$96 Chicago, Illinois The Westin Michigan Avenue Chicago in Nov: $96 & Up
Expedia
$80 Chicago, Illinois Congress Plaza on Sale: Book 3 Nts in Nov Fr $80+/Nt
Expedia
$103 Chicago, Illinois Hostelling International Chicago in Nov: $103 & Up
Expedia
$86 Chicago, Illinois Book 3 Nts in Chicago this Nov Fr $86+/Nt
Save with Expedia, $15/night less
$96 Chicago, Illinois Chicago Savings! Book at W Chicago Lakeshore Fr $96+/Nt
Expedia
$100 Chicago, Illinois Chicago Savings! Book 3 Nts in Nov Fr $100+/Nt
Expedia
$144 Chicago, Illinois Book the W Chicago - City Center 3 Nts in Nov Fr $144+/Nt
Expedia
$99 Chicago, Illinois Book 3.5-Star Crowne Plaza Chicago - The Metro Fr $99+/Nt
Expedia
$99 Chicago, Illinois Save at 4-Star The Drake: $99 & Up in Nov
Expedia
$125 Chicago, Illinois Chicago Marriott at Medical District/UIC in Nov: $125 & Up
Expedia
$80 Chicago, Illinois Book 4-Star MileNorth, A Chicago Fr $80+/Nt
Save with Expedia, $19/night less
$109 Chicago, Illinois Special deal: 3-Star Residence Inn Chicago Downtown Fr $109+/Nt
Expedia
$264 Chicago, Illinois The Ritz-Carlton Chicago (A Four Seasons ) in Nov: $264 & Up
Save with Expedia, $131/night less
$134 Chicago, Illinois Book the The Blackstone A Renaissance 3 Nts in Nov Fr $134+/Nt
Expedia
$76 Chicago, Illinois Crowne Plaza Chicago Magnificent Mile in Nov: $76 & Up
Expedia
$127 Chicago, Illinois Save Big This Nov! Book 3 Nts at Hard Rock Chicago Fr $127+/Nt
Save with Expedia, $22/night less
$159 Chicago, Illinois Chicago Savings! Book at Renaissance Chicago Fr $159+/Nt
Expedia
$110 Chicago, Illinois Book 4-Star Hyatt Chicago Magnificent Mile in Chicago Fr $110+/Nt
Expedia
$130 Chicago, Illinois Nov deal: Raffaello Fr $130+/Nt
Save with Expedia, $69/night less
$85 Chicago, Illinois Doubletree by Hilton Chicago Magnificent Mile in Nov: $85 & Up
Expedia
$90 Chicago, Illinois Chicago Savings! Book at BEST WESTERN River North Fr $90+/Nt
Expedia
$80 Chicago, Illinois Special deal: 4-Star Warwick Allerton Chicago Fr $80+/Nt
Save with Expedia, $37/night less
$297 Chicago, Illinois Special deal: 5-Star The Peninsula Chicago Fr $297+/Nt
Save with Expedia, $148/night less
$68 Chicago, Illinois Travelodge Chicago Downtown in Nov: $68 & Up
Expedia
$90 Chicago, Illinois Club Quarters Chicago - Central Loop in Nov: $90 & Up
Save with Expedia, $9/night less
$109 Chicago, Illinois Special deal: 4-Star Allegro Chicago - a Kimpton Fr $109+/Nt
Expedia
$84 Chicago, Illinois Book 3.5-Star Hilton Suites Chicago/Magnificent Mile Fr $84+/Nt
Expedia
$89 Chicago, Illinois Chicago Savings! Book at Holiday Inn Express Cass Fr $89+/Nt
Expedia
$80 Chicago, Illinois Chicago Savings! Book 3 Nts in Nov Fr $80+/Nt
Expedia
$84 Chicago, Illinois Chicago Downtown, Autograph Collection in Nov: $84 & Up
Save with Expedia, $35/night less
$76 Chicago, Illinois Small budget: Stay in Chicago this Nov Fr $76+/Nt
Expedia
$129 Chicago, Illinois Book the theWit - A DoubleTree by Hilton 3 Nts in Nov Fr $129+/Nt
Expedia
$79 Chicago, Illinois Book 3-Star Chicago's Essex Inn in Chicago Fr $79+/Nt
Expedia
$102 Chicago, Illinois Chicago Savings! Book at InterContinental Chicago Fr $102+/Nt
Expedia
$111 Chicago, Illinois Courtyard Chicago Downtown/Magnificent Mile in Nov: $111 & Up
Expedia
$93 Chicago, Illinois Book 4-Star The Palmer House Hilton in Chicago Fr $93+/Nt
Expedia
$79 Chicago, Illinois Chicago Savings! Book 3 Nts in Nov Fr $79+/Nt
Expedia
$62 Chicago, Illinois Red Roof Inn Chicago Downtown Magnificent Mile in Nov: $62 & Up
Save with Expedia, $15/night less
$87 Chicago, Illinois Book the Holiday Inn Chicago Downtown 3 Nts in Nov Fr $87+/Nt
Expedia
$76 Chicago, Illinois The Tremont Chicago at Magnificent Mile in Nov: $76 & Up
Expedia
$109 Chicago, Illinois Book in Chicago: Save this Nov Fr $109+/Nt
Expedia
$136 Chicago, Illinois Fairmont Chicago Millennium Park in Nov: $136 & Up
Save with Expedia, $23/night less
$112 Chicago, Illinois Small budget: Book Radisson Blu Aqua 3 Nts in Nov Fr $112+/Nt
Expedia
$304 Chicago, Illinois Book 3 Nts in Chicago this Nov Fr $304+/Nt
Expedia
$120 Chicago, Illinois $120 & Up: Swissotel Chicago 4-Star Hotel in Chicago
Save with Expedia, $30/night less
$139 Chicago, Illinois Chicago Savings! Book at Burnham - a Kimpton Fr $139+/Nt
Expedia
$119 Chicago, Illinois Book in Chicago: Save at the Omni Chicago in Nov Fr $119+/Nt
Expedia
$90 Chicago, Illinois Book in Chicago: Save this Nov Fr $90+/Nt
Expedia
$144 Chicago, Illinois Small budget: Book The James Chicago 3 Nts in Nov Fr $144+/Nt
Save with Expedia, $25/night less
$259 Chicago, Illinois Book 3 Nts in Chicago this Nov Fr $259+/Nt
Save with Expedia, $86/night less
$64 Chicago, Illinois Save Big This Nov! Book 3 Nts in Chicago Fr $64+/Nt
Expedia
$96 Chicago, Illinois Chicago Savings! Book 3 Nts in Nov Fr $96+/Nt
Expedia
$99 Chicago, Illinois Nov deal: Homewood Suites by Hilton Chicago Downtown Fr $99+/Nt
Expedia
$84 Chicago, Illinois Chicago Savings! Book at Central Loop Fr $84+/Nt
Save with Expedia, $9/night less
$269 Chicago, Illinois Chicago Savings! Book at Majestic Fr $269+/Nt
Expedia
$99 Chicago, Illinois Book in Chicago: Save this Nov Fr $99+/Nt
Expedia
$655 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $655
Expedia
$513 Chicago, Illinois Save at 3.5-Star Hotel: 3 Nts + Air to Chicago Fr $513
Expedia
$440 Chicago, Illinois Save at 3.5-Star Hotel: 3 Nts + Air to Chicago Fr $440
Expedia
$454 Chicago, Illinois 4.5-Star Chicago Sale! 3 Nts + Air Fr $454
Expedia
$880 Chicago, Illinois Chicago 4.5-Star Hotel Sale! 3 Nts + Air Fr $880
Expedia
$465 Chicago, Illinois 3.5-Star Chicago Sale! 3 Nts + Air Fr $465
Expedia
$119 Bedford Park, Illinois Hampton Inn Chicago-Midway Airport in Nov: $119 & Up
Expedia
$62 Bridgeview, Illinois Book 3 Nts in Bridgeview this Nov Fr $62+/Nt
Expedia
$87 Westchester, Illinois Hampton Inn Chicago/Westchester (Oak Brook) in Nov: $87 & Up
Expedia
$74 Countryside, Illinois BEST WESTERN Chicagoland - Countryside in Nov: $74 & Up
Save with Expedia, $19/night less
$52 Schiller Park, Illinois Book in Schiller Park: Save this Nov Fr $52+/Nt
Save with Expedia, $43/night less
$78 Schiller Park, Illinois Save Big This Nov! Book 3 Nts in Schiller Park Fr $78+/Nt
Save with Expedia, $19/night less
$80 Schiller Park, Illinois Four Points by Sheraton Chicago O'Hare Airport in Nov: $80 & Up
Expedia
$110 Alsip, Illinois Alsip Savings! Book 3 Nts in Nov Fr $110+/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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