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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$200 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$111 Chicago, Illinois Save Big This Nov! Book 3 Nts in Chicago Fr $111+/Nt
Expedia
$121 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
$200 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$112+ Chicago, Illinois 4.5 Star Luxury Chicago Hotel on Sale! Starting from $112/nt
Jetsetter
$200 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$104 Chicago, Illinois $104 & Up: The Silversmith 3.5-Star Hotel in Chicago
Save with Expedia, $19/night less
$169 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$113 Chicago, Illinois Book in Chicago: Save this Nov Fr $113+/Nt
Save with Expedia, $20/night less
$112 Chicago, Illinois Southwest Airlines Early Black Friday Savings
DealBase.com
$113 Chicago, Illinois Nov deal: Wyndham Grand Chicago Riverfront Fr $113+/Nt
Save with Expedia, $20/night less
$130 Chicago, Illinois Southwest Airlines Early Black Friday Savings
DealBase.com
$88 Chicago, Illinois InterContinental Chicago on Sale: Book 3 Nts in Nov Fr $88+/Nt
Expedia
$131 Chicago, Illinois Southwest Airlines Early Black Friday Savings
DealBase.com
$85 Chicago, Illinois Book 4-Star Hilton Chicago in Chicago Fr $85+/Nt
Expedia
$200 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$84 Chicago, Illinois Chicago Savings! Book 3 Nts in Nov Fr $84+/Nt
Expedia
$179 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$99 Chicago, Illinois Book 3 Nts in Chicago this Nov Fr $99+/Nt
Expedia
$128 Chicago, Illinois Southwest Airlines Early Black Friday Savings
DealBase.com
$149 Chicago, Illinois Book 4-Star JW Marriott Chicago in Chicago Fr $149+/Nt
Expedia
$125+ Chicago, Illinois Chicago on Sale! Starting From $125/nt
Jetsetter
$81 Chicago, Illinois Book 3 Nts in Chicago this Nov Fr $81+/Nt
Save with Expedia, $8/night less
$85+ Chicago, Illinois 4-Star Chicago Hotels from $85
trivago
$129 Chicago, Illinois Book in Chicago: Save this Nov Fr $129+/Nt
Expedia
$99 Chicago, Illinois Special deal: 3.5-Star Embassy Suites Chicago Downtown Fr $99+/Nt
Expedia
$120 Chicago, Illinois Chicago Savings! Book 3 Nts in Nov Fr $120+/Nt
Expedia
$80 Chicago, Illinois Nov deal: Holiday Inn Chicago Mart Plaza River North Fr $80+/Nt
Expedia
$95 Chicago, Illinois Book 3 Nts in Chicago this Nov Fr $95+/Nt
Expedia
$93 Chicago, Illinois Chicago Savings! Book at Hilton Chicago O'Hare Airport Fr $93+/Nt
Expedia
$109 Chicago, Illinois Save Big This Nov! Book 3 Nts at dana and spa Fr $109+/Nt
Expedia
$100 Chicago, Illinois Chicago Savings! Book at Sheraton Chicago and Towers Fr $100+/Nt
Expedia
$99 Chicago, Illinois Nov deal: Homewood Suites by Hilton Chicago Downtown Fr $99+/Nt
Expedia
$80 Chicago, Illinois Book 3-Star Congress Plaza Fr $80+/Nt
Expedia
$103 Chicago, Illinois Save Big This Nov! Book 3 Nts in Chicago Fr $103+/Nt
Expedia
$86 Chicago, Illinois Chicago Savings! Book at ACME Company Chicago Fr $86+/Nt
Save with Expedia, $15/night less
$96 Chicago, Illinois Save at 4-Star W Chicago Lakeshore: $96 & Up in Nov
Expedia
$100 Chicago, Illinois Indigo Chicago Downtown Gold Coast in Nov: $100 & Up
Expedia
$144 Chicago, Illinois Chicago Savings! Book at W Chicago - City Center Fr $144+/Nt
Expedia
$99 Chicago, Illinois Nov deal: Crowne Plaza Chicago - The Metro Fr $99+/Nt
Expedia
$99 Chicago, Illinois Book 3 Nts in Chicago this Nov Fr $99+/Nt
Expedia
$125 Chicago, Illinois Nov deal: Chicago Marriott at Medical District/UIC Fr $125+/Nt
Expedia
$101 Chicago, Illinois Book 4-Star The Westin Chicago River North Fr $101+/Nt
Expedia
$264 Chicago, Illinois Save in Chicago: Book 3 Nts in Nov Fr $264+/Nt
Save with Expedia, $131/night less
$80 Chicago, Illinois Book in Chicago: Save this Nov Fr $80+/Nt
Save with Expedia, $19/night less
$109 Chicago, Illinois Small budget: Stay in Chicago this Nov Fr $109+/Nt
Expedia
$76 Chicago, Illinois Save Big This Nov! Book 3 Nts in Chicago Fr $76+/Nt
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 Book in Chicago: Save this Nov Fr $159+/Nt
Expedia
$110 Chicago, Illinois Nov deal: Hyatt Chicago Magnificent Mile Fr $110+/Nt
Expedia
$130 Chicago, Illinois Book the Raffaello 3 Nts in Nov Fr $130+/Nt
Save with Expedia, $69/night less
$80 Chicago, Illinois Warwick Allerton Chicago in Nov: $80 & Up
Save with Expedia, $37/night less
$85 Chicago, Illinois Save in Chicago: Book 3 Nts in Nov Fr $85+/Nt
Expedia
$90 Chicago, Illinois Save in Chicago: Book 3 Nts in Nov Fr $90+/Nt
Expedia
$297 Chicago, Illinois Special deal: 5-Star The Peninsula Chicago Fr $297+/Nt
Save with Expedia, $148/night less
$68 Chicago, Illinois Chicago Savings! Book at Travelodge Chicago Downtown Fr $68+/Nt
Expedia
$90 Chicago, Illinois Nov deal: Club Quarters Chicago - Central Loop Fr $90+/Nt
Save with Expedia, $9/night less
$113 Chicago, Illinois Book in Chicago: Save this Nov Fr $113+/Nt
Expedia
$109 Chicago, Illinois Chicago Savings! Book at Allegro Chicago - a Kimpton Fr $109+/Nt
Expedia
$84 Chicago, Illinois Book 3.5-Star Hilton Suites Chicago/Magnificent Mile Fr $84+/Nt
Expedia
$80 Chicago, Illinois Chicago Savings! Book at BEST WESTERN Grant Park Fr $80+/Nt
Expedia
$89 Chicago, Illinois Save Big This Nov! Book 3 Nts in Chicago Fr $89+/Nt
Expedia
$76 Chicago, Illinois Book in Chicago: Save this Nov Fr $76+/Nt
Expedia
$84 Chicago, Illinois Chicago Downtown, Autograph Collection in Nov: $84 & Up
Save with Expedia, $35/night less
$129 Chicago, Illinois Book 3 Nts in Chicago this Nov Fr $129+/Nt
Expedia
$79 Chicago, Illinois Nov deal: Chicago's Essex Inn Fr $79+/Nt
Expedia
$244 Chicago, Illinois Nov deal: Park Hyatt Chicago Fr $244+/Nt
Expedia
$129 Chicago, Illinois Chicago Savings! Book 3 Nts in Nov Fr $129+/Nt
Expedia
$111 Chicago, Illinois Nov deal: Courtyard Chicago Downtown/Magnificent Mile Fr $111+/Nt
Expedia
$93 Chicago, Illinois Special deal: 4-Star The Palmer House Hilton Fr $93+/Nt
Expedia
$79 Chicago, Illinois Book 3 Nts in Chicago this Nov Fr $79+/Nt
Expedia
$76 Chicago, Illinois Chicago Savings! Book 3 Nts in Nov Fr $76+/Nt
Expedia
$81 Chicago, Illinois Save in Chicago: Book 3 Nts in Nov at Central Loop Fr $81+/Nt
Save with Expedia, $8/night less
$62 Chicago, Illinois Chicago Savings! Book 3 Nts in Nov Fr $62+/Nt
Save with Expedia, $15/night less
$87 Chicago, Illinois Book 3 Nts in Chicago this Nov Fr $87+/Nt
Expedia
$109 Chicago, Illinois Save in Chicago: Book 3 Nts in Nov Fr $109+/Nt
Expedia
$136 Chicago, Illinois Chicago Savings! Book 3 Nts in Nov Fr $136+/Nt
Save with Expedia, $23/night less
$112 Chicago, Illinois Book 3 Nts in Chicago this Nov Fr $112+/Nt
Expedia
$304 Chicago, Illinois Chicago Savings! Book 3 Nts in Nov Fr $304+/Nt
Expedia
$159 Chicago, Illinois Conrad Chicago on Sale: Book 3 Nts in Nov Fr $159+/Nt
Expedia
$120 Chicago, Illinois Book in Chicago: Save this Nov Fr $120+/Nt
Save with Expedia, $30/night less
$89 Chicago, Illinois Hampton Majestic Chicago Theatre District in Nov: $89 & Up
Expedia
$119 Chicago, Illinois Save Big This Nov! Book 3 Nts at Omni Chicago Fr $119+/Nt
Expedia
$90 Chicago, Illinois Chicago Savings! Book 3 Nts in Nov Fr $90+/Nt
Expedia
$207 Chicago, Illinois Save Big This Nov! Book 3 Nts in Chicago Fr $207+/Nt
Expedia
$60 Chicago, Illinois Small budget: Stay in Chicago this Nov Fr $60+/Nt
Save with Expedia, $25/night less
$259 Chicago, Illinois Book 5-Star Trump International & Tower Chicago Fr $259+/Nt
Save with Expedia, $86/night less
$144 Chicago, Illinois The James Chicago on Sale: Book 3 Nts in Nov Fr $144+/Nt
Save with Expedia, $25/night less
$99 Chicago, Illinois Special deal: 4-Star Hyatt Regency Chicago Fr $99+/Nt
Expedia
$781 Chicago, Illinois 3.5-Star Chicago Sale! 3 Nts + Air Fr $781
Expedia
$1,181 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $1,181
Expedia
$696 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $696
Expedia
$475 Chicago, Illinois 4.5-Star Chicago Sale! 3 Nts + Air Fr $475
Expedia
$3,534 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $3,534
Expedia
$697 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $697
Expedia
$783 Chicago, Illinois Chicago 3.5-Star Hotel Sale! 3 Nts + Air Fr $783
Expedia
$73 Bensenville, Illinois Book in Bensenville: Save this Nov Fr $73+/Nt
Expedia
$91 Arlington Heights, Illinois DoubleTree by Hilton Chicago - Arlington Heights in Nov: $91 & Up
Expedia
$66 Schiller Park, Illinois Schiller Park Savings! Book at O'Hare Inn & Suites Fr $66+/Nt
Save with Expedia, $43/night less
PRICEDESTINATIONDEAL
$283 Newark, New Jersey Cheap Flights from Phoenix
DealBase.com
$220 Newark, New Jersey Cheap Flights from Raleigh
DealBase.com
$219 Newark, New Jersey 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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