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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$99+ Chicago, Illinois Save Up To 25% on 4-Star Chicago Hotels
trivago
$167 Chicago, Illinois Book Today and Save + Free Breakfast Daily
BookIt.com
$79 Chicago, Illinois Chicago Savings! Book at Hyatt Regency McCormick Place Fr $79+/Nt
Expedia
$112+ Chicago, Illinois 4.5 Star Luxury Chicago Hotel on Sale! Starting from $112/nt
Jetsetter
$109 Chicago, Illinois Travelodge Chicago Downtown in Sep: $109 & Up
Expedia
$522 Chicago, Illinois Great Rates in Chicago + Breakfast!
DealBase.com
$112 Chicago, Illinois Book 3 Nts in Chicago this Aug Fr $112+/Nt
Expedia
$261 Chicago, Illinois WestJet Great City Escapes Sale
DealBase.com
$179 Chicago, Illinois Chicago Marriott Downtown Magnificent Mile in Aug: $179 & Up
Expedia
$277 Chicago, Illinois WestJet Great City Escapes Sale
DealBase.com
$125+ Chicago, Illinois Chicago on Sale! Starting From $125/nt
Jetsetter
$119 Chicago, Illinois Book 4-Star Hilton Chicago O'Hare Airport in Chicago Fr $119+/Nt
Expedia
$181 Chicago, Illinois Chicago Savings! Book 3 Nts in Aug Fr $181+/Nt
Expedia
$219 Chicago, Illinois Save in Chicago: Book 3 Nts in Aug Fr $219+/Nt
Expedia
$240 Chicago, Illinois Special deal: 4.5-Star The James Chicago Fr $240+/Nt
Save with Expedia, $43/night less
$188 Chicago, Illinois Small budget: Stay in Chicago this Sep Fr $188+/Nt
Expedia
$246 Chicago, Illinois Chicago Savings! Book 3 Nts in Aug Fr $246+/Nt
Expedia
$723 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $723
Expedia
$307 Chicago, Illinois Chicago Savings! Book at Four Seasons Chicago Fr $307+/Nt
Save with Expedia, $145/night less
$290 Chicago, Illinois Sep deal: Holiday Inn Express Chicago-Midway Airport Fr $290+/Nt
Expedia
$103 Chicago, Illinois Save in Chicago: Book 3 Nts in Sep Fr $103+/Nt
Expedia
$649 Chicago, Illinois Chicago 3.5-Star Hotel Sale! 3 Nts + Air Fr $649
Expedia
$201 Chicago, Illinois Aug deal: Fairmont Chicago Millennium Park Fr $201+/Nt
Save with Expedia, $35/night less
$199 Chicago, Illinois Small budget: Stay in Chicago this Aug Fr $199+/Nt
Expedia
$169 Chicago, Illinois Allegro Chicago - a Kimpton in Sep: $169 & Up
Expedia
$183 Chicago, Illinois Burnham - a Kimpton on Sale: Book 3 Nts in Aug Fr $183+/Nt
Expedia
$407 Chicago, Illinois Book 5-Star Trump International & Tower Chicago Fr $407+/Nt
Save with Expedia, $102/night less
$96 Chicago, Illinois The Tremont Chicago at Magnificent Mile in Aug: $96 & Up
Expedia
$178 Chicago, Illinois Sep deal: Hampton Majestic Chicago Theatre District Fr $178+/Nt
Expedia
$226 Chicago, Illinois Aug deal: MileNorth, A Chicago Fr $226+/Nt
Expedia
$751 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $751
Expedia
$197 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $197+/Nt
Expedia
$211 Chicago, Illinois Aug deal: Sheraton Chicago and Towers Fr $211+/Nt
Expedia
$156 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $156+/Nt
Save with Expedia, $28/night less
$162 Chicago, Illinois Aug deal: Homewood Suites by Hilton Chicago Downtown Fr $162+/Nt
Expedia
$116 Chicago, Illinois Aug deal: Holiday Inn Chicago Mart Plaza River North Fr $116+/Nt
Expedia
$215 Chicago, Illinois Save Big This Aug! Book 3 Nts in Chicago Fr $215+/Nt
Save with Expedia, $7/night less
$183 Chicago, Illinois Book 3.5-Star Buckingham Athletic Club in Chicago Fr $183+/Nt
Expedia
$279 Chicago, Illinois Chicago Savings! Book 3 Nts in Sep Fr $279+/Nt
Expedia
$1,050 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $1,050
Expedia
$120 Chicago, Illinois Save Big This Aug! Book 3 Nts at Chicago's Essex Inn Fr $120+/Nt
Expedia
$219 Chicago, Illinois Small budget: Stay in Chicago this Sep Fr $219+/Nt
Expedia
$682 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $682
Expedia
$305 Chicago, Illinois $305 & Up: Conrad Chicago 4.5-Star Hotel in Chicago
Expedia
$121 Chicago, Illinois Special deal: 3-Star ACME Company Chicago Fr $121+/Nt
Save with Expedia, $22/night less
$142 Chicago, Illinois Book 3-Star Holiday Inn Chicago O'Hare Fr $142+/Nt
Expedia
$109 Chicago, Illinois Doubletree by Hilton Chicago Magnificent Mile in Aug: $109 & Up
Expedia
$166 Chicago, Illinois Embassy Suites Chicago Downtown Lakefront in Aug: $166 & Up
Expedia
$269 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $269+/Nt
Expedia
$216 Chicago, Illinois Sofitel Chicago Water Tower in Sep: $216 & Up
Expedia
$269 Chicago, Illinois $269 & Up: Kinzie 3.5-Star Hotel in Chicago
Expedia
$193 Chicago, Illinois Save in Chicago: Book 3 Nts in Aug Fr $193+/Nt
Expedia
$144 Chicago, Illinois InterContinental Chicago on Sale: Book 3 Nts in Aug Fr $144+/Nt
Expedia
$111 Chicago, Illinois Book 3.5-Star River in Chicago Fr $111+/Nt
Save with Expedia, $12/night less
$193 Chicago, Illinois Book 3.5-Star The Silversmith in Chicago Fr $193+/Nt
Expedia
$137 Chicago, Illinois Save in Chicago: Book 3 Nts in Sep Fr $137+/Nt
Expedia
$283 Chicago, Illinois City Suites in Sep: $283 & Up
Expedia
$150 Chicago, Illinois Small budget: Stay in Chicago this Aug Fr $150+/Nt
Expedia
$127 Chicago, Illinois Chicago Savings! Book at Chicago South Loop Fr $127+/Nt
Save with Expedia, $22/night less
$198 Chicago, Illinois Special deal: 4-Star Millennium Knickerbocker Chicago Fr $198+/Nt
Save with Expedia, $35/night less
$169 Chicago, Illinois Small budget: Stay in Chicago this Aug Fr $169+/Nt
Expedia
$126 Chicago, Illinois Book in Chicago: Save at the Congress Plaza in Aug Fr $126+/Nt
Expedia
$116 Chicago, Illinois $116 & Up: Holiday Inn Express Cass 3-Star Hotel in Chicago
Expedia
$162 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $162+/Nt
Expedia
$150 Chicago, Illinois Save in Chicago: Book 3 Nts in Aug Fr $150+/Nt
Save with Expedia, $37/night less
$279 Chicago, Illinois Chicago Savings! Book at Palomar Chicago, a Kimpton Fr $279+/Nt
Expedia
$216 Chicago, Illinois Chicago Savings! Book at Monaco Chicago - a Kimpton Fr $216+/Nt
Expedia
$169 Chicago, Illinois $169 & Up: Comfort Suites Michigan Avenue 3-Star Hotel in Chicago
Expedia
$191 Chicago, Illinois Book 3.5-Star Crowne Plaza Chicago - The Metro Fr $191+/Nt
Expedia
$188 Chicago, Illinois Book in Chicago: Save this Aug Fr $188+/Nt
Expedia
$475 Chicago, Illinois Book in Chicago: Save this Aug Fr $475+/Nt
Expedia
$232 Chicago, Illinois Special deal: 4-Star Raffaello Fr $232+/Nt
Save with Expedia, $125/night less
$160 Chicago, Illinois Book the BEST WESTERN River North 3 Nts in Aug Fr $160+/Nt
Expedia
$119 Chicago, Illinois Save in Chicago: Book 3 Nts in Aug Fr $119+/Nt
Expedia
$671 Chicago, Illinois Save at 3.5-Star Hotel: 3 Nts + Air to Chicago Fr $671
Expedia
$462 Chicago, Illinois Chicago Savings! Book at Waldorf Astoria Chicago Fr $462+/Nt
Expedia
$264 Chicago, Illinois Aug deal: The Ritz-Carlton Chicago (A Four Seasons ) Fr $264+/Nt
Save with Expedia, $131/night less
$183 Chicago, Illinois The Palmer House Hilton on Sale: Book 3 Nts in Aug Fr $183+/Nt
Expedia
$229 Chicago, Illinois Book the Residence Inn Chicago Downtown 3 Nts in Sep Fr $229+/Nt
Expedia
$171 Chicago, Illinois Holiday Inn Chicago Downtown in Sep: $171 & Up
Expedia
$235 Chicago, Illinois Book 4-Star The Westin Chicago River North Fr $235+/Nt
Expedia
$105 Chicago, Illinois Aug deal: Club Quarters Chicago - Central Loop Fr $105+/Nt
Save with Expedia, $11/night less
$169 Chicago, Illinois Save Big This Aug! Book 3 Nts at Blake Chicago Fr $169+/Nt
Expedia
$149 Chicago, Illinois Small budget: Stay in Chicago this Aug Fr $149+/Nt
Save with Expedia, $50/night less
$194 Chicago, Illinois Aug deal: Courtyard Chicago Downtown/Magnificent Mile Fr $194+/Nt
Expedia
$315 Chicago, Illinois Book 4-Star Radisson Blu Aqua Fr $315+/Nt
Expedia
$149 Chicago, Illinois Small budget: Stay in Chicago this Aug Fr $149+/Nt
Expedia
$129 Chicago, Illinois Book in Chicago: Save this Sep Fr $129+/Nt
Save with Expedia, $14/night less
$179 Chicago, Illinois The Drake on Sale: Book 3 Nts in Aug Fr $179+/Nt
Expedia
$126 Chicago, Illinois Warwick Allerton Chicago on Sale: Book 3 Nts in Sep Fr $126+/Nt
Save with Expedia, $42/night less
$253 Chicago, Illinois Small budget: Book dana and spa 3 Nts in Sep Fr $253+/Nt
Expedia
$319 Chicago, Illinois Special deal: 5-Star Park Hyatt Chicago Fr $319+/Nt
Expedia
$259 Chicago, Illinois Book in Chicago: Save this Aug Fr $259+/Nt
Expedia
$246 Chicago, Illinois Chicago Savings! Book at Hard Rock Chicago Fr $246+/Nt
Expedia
$154 Chicago, Illinois Crowne Plaza Chicago Magnificent Mile in Aug: $154 & Up
Expedia
$179 Chicago, Illinois Save Big This Aug! Book 3 Nts at Hilton Chicago Fr $179+/Nt
Expedia
$224 Chicago, Illinois The Blackstone A Renaissance in Aug: $224 & Up
Expedia
$199 Chicago, Illinois Book 4-Star Hyatt Regency Chicago in Chicago Fr $199+/Nt
Expedia
$80 Glenview, Illinois Glenview Savings! Book at Wyndham Glenview Suites Fr $80+/Nt
Save with Expedia, $20/night less
$136 Evanston, Illinois Evanston Savings! Book at Hilton Garden Inn Evanston Fr $136+/Nt
Expedia
PRICEDESTINATIONDEAL
$121 New York City, New York Cheap Flights from Washington, DC
DealBase.com
$237 New York City, New York Cheap Flights from St. Louis
DealBase.com
$169 New York City, New York Cheap Flights from Charlotte
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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