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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$52 Chicago, Illinois Frontier Airlines Washington-Dulles Sale
DealBase.com
$99+ Chicago, Illinois Save Up To 25% on 4-Star Chicago Hotels
trivago
$522 Chicago, Illinois Great Rates in Chicago + Breakfast!
DealBase.com
$172 Chicago, Illinois Chicago Savings! Book at Holiday Inn Chicago Downtown Fr $172+/Nt
Expedia
$125+ Chicago, Illinois Chicago on Sale! Starting From $125/nt
Jetsetter
$159 Chicago, Illinois Book in Chicago: Save this Aug Fr $159+/Nt
Expedia
$315 Chicago, Illinois WestJet Great Fares to Chicago.
DealBase.com
$324 Chicago, Illinois Book 5-Star Park Hyatt Chicago in Chicago Fr $324+/Nt
Save with Expedia, $81/night less
$281 Chicago, Illinois WestJet Great Fares to Chicago.
DealBase.com
$156 Chicago, Illinois Save in Chicago: Book 3 Nts in Aug at Hilton Chicago Fr $156+/Nt
Expedia
$112+ Chicago, Illinois 4.5 Star Luxury Chicago Hotel on Sale! Starting from $112/nt
Jetsetter
$127 Chicago, Illinois Chicago South Loop on Sale: Book 3 Nts in Aug Fr $127+/Nt
Save with Expedia, $22/night less
$162 Chicago, Illinois Book in Chicago: Save this Aug Fr $162+/Nt
Expedia
$215 Chicago, Illinois Book in Chicago: Save at the Radisson Blu Aqua in Aug Fr $215+/Nt
Expedia
$124 Chicago, Illinois Chicago Savings! Book at Holiday Inn Express Cass Fr $124+/Nt
Expedia
$156 Chicago, Illinois Save Big This Aug! Book 3 Nts in Chicago Fr $156+/Nt
Save with Expedia, $28/night less
$219 Chicago, Illinois Save Big This Aug! Book 3 Nts in Chicago Fr $219+/Nt
Expedia
$176 Chicago, Illinois Small budget: Book W Chicago Lakeshore 3 Nts in Aug Fr $176+/Nt
Expedia
$194 Chicago, Illinois Holiday Inn Express Chicago-Midway Airport in Aug: $194 & Up
Expedia
$117 Chicago, Illinois Chicago Savings! Book at Warwick Allerton Chicago Fr $117+/Nt
Save with Expedia, $63/night less
$163 Chicago, Illinois Small budget: Stay in Chicago this Aug Fr $163+/Nt
Expedia
$112 Chicago, Illinois Aug deal: Howard Johnson Inn Downtown Chicago Fr $112+/Nt
Expedia
$266 Chicago, Illinois Save in Chicago: Book 3 Nts in Aug Fr $266+/Nt
Save with Expedia, $133/night less
$126 Chicago, Illinois Small budget: Book Central Loop 3 Nts in Aug Fr $126+/Nt
Save with Expedia, $13/night less
$140 Chicago, Illinois Book 3-Star BEST WESTERN River North Fr $140+/Nt
Expedia
$163 Chicago, Illinois Small budget: Book Chicago's Essex Inn 3 Nts in Aug Fr $163+/Nt
Expedia
$132 Chicago, Illinois Book in Chicago: Save this Aug Fr $132+/Nt
Expedia
$144 Chicago, Illinois Chicago Savings! Book at InterContinental Chicago Fr $144+/Nt
Expedia
$119 Chicago, Illinois Book 4-Star Hilton Chicago O'Hare Airport in Chicago Fr $119+/Nt
Expedia
$188 Chicago, Illinois Chicago Savings! Book 3 Nts in Aug Fr $188+/Nt
Expedia
$154 Chicago, Illinois Save Big This Aug! Book 3 Nts in Chicago Fr $154+/Nt
Save with Expedia, $38/night less
$159 Chicago, Illinois Save in Chicago: Book 3 Nts in Aug Fr $159+/Nt
Expedia
$186 Chicago, Illinois Book the MileNorth, A Chicago 3 Nts in Aug Fr $186+/Nt
Expedia
$305 Chicago, Illinois Aug deal: Conrad Chicago Fr $305+/Nt
Expedia
$279 Chicago, Illinois Chicago Savings! Book at JW Marriott Chicago Fr $279+/Nt
Expedia
$218 Chicago, Illinois The Silversmith in Aug: $218 & Up
Save with Expedia, $38/night less
$170 Chicago, Illinois Save Big This Aug! Book 3 Nts in Chicago Fr $170+/Nt
Expedia
$309 Chicago, Illinois Aug deal: The Willows Fr $309+/Nt
Expedia
$199 Chicago, Illinois Save at 3-Star Comfort Suites Michigan Avenue: $199 & Up in Aug
Expedia
$270 Chicago, Illinois Four Seasons Chicago in Aug: $270 & Up
Save with Expedia, $135/night less
$199 Chicago, Illinois Book 3 Nts in Chicago this Aug Fr $199+/Nt
Expedia
$187 Chicago, Illinois Aug deal: Fairmont Chicago Millennium Park Fr $187+/Nt
Save with Expedia, $32/night less
$79 Chicago, Illinois Hyatt Regency McCormick Place in Aug: $79 & Up
Expedia
$153 Chicago, Illinois Book 4-Star Raffaello Fr $153+/Nt
Save with Expedia, $82/night less
$176 Chicago, Illinois Indigo Chicago Downtown Gold Coast in Aug: $176 & Up
Expedia
$127 Chicago, Illinois Book 3 Nts in Chicago this Aug Fr $127+/Nt
Save with Expedia, $22/night less
$182 Chicago, Illinois Book 3.5-Star Crowne Plaza Chicago - The Metro Fr $182+/Nt
Expedia
$224 Chicago, Illinois Chicago Savings! Book at The Blackstone A Renaissance Fr $224+/Nt
Expedia
$179 Chicago, Illinois Book 4-Star Hard Rock Chicago Fr $179+/Nt
Expedia
$96 Chicago, Illinois Book 3-Star The Tremont Chicago at Magnificent Mile Fr $96+/Nt
Expedia
$279 Chicago, Illinois Chicago Savings! Book at Palomar Chicago, a Kimpton Fr $279+/Nt
Expedia
$110 Chicago, Illinois Book in Chicago: Save this Aug Fr $110+/Nt
Expedia
$169 Chicago, Illinois Book 3.5-Star Embassy Suites Chicago Downtown Fr $169+/Nt
Expedia
$256 Chicago, Illinois Small budget: Stay in Chicago this Aug Fr $256+/Nt
Expedia
$187 Chicago, Illinois Chicago Savings! Book at Sofitel Chicago Water Tower Fr $187+/Nt
Expedia
$200 Chicago, Illinois Small budget: Stay in Chicago this Aug Fr $200+/Nt
Expedia
$156 Chicago, Illinois Save in Chicago: Book 3 Nts in Aug Fr $156+/Nt
Save with Expedia, $17/night less
$174 Chicago, Illinois Book 3-Star ACME Company Chicago Fr $174+/Nt
Save with Expedia, $15/night less
$299 Chicago, Illinois Chicago Savings! Book at Renaissance Chicago Fr $299+/Nt
Expedia
$129 Chicago, Illinois Book in Chicago: Save this Aug Fr $129+/Nt
Save with Expedia, $23/night less
$132 Chicago, Illinois Book in Chicago: Save this Aug Fr $132+/Nt
Expedia
$235 Chicago, Illinois Book 4-Star The Westin Chicago River North in Chicago Fr $235+/Nt
Expedia
$127 Chicago, Illinois Book in Chicago: Save this Aug Fr $127+/Nt
Expedia
$1,382 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $1,382
Expedia
$765 Chicago, Illinois Save at 3.5-Star Hotel: 3 Nts + Air to Chicago Fr $765
Expedia
$2,236 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $2,236
Expedia
$808 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $808
Expedia
$132 Chicago, Illinois Small budget: Book PUBLIC Chicago 3 Nts in Aug Fr $132+/Nt
Save with Expedia, $33/night less
$181 Chicago, Illinois Book in Chicago: Save at the The James Chicago in Aug Fr $181+/Nt
Save with Expedia, $32/night less
$269 Chicago, Illinois Book in Chicago: Save this Aug Fr $269+/Nt
Expedia
$394 Chicago, Illinois Book 5-Star Trump International & Tower Chicago Fr $394+/Nt
Save with Expedia, $98/night less
$119 Chicago, Illinois Travelodge Chicago Downtown in Aug: $119 & Up
Expedia
$1,516 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $1,516
Expedia
$144 Chicago, Illinois Book in Chicago: Save at the Days Inn Chicago in Aug Fr $144+/Nt
Expedia
$196 Chicago, Illinois Aug deal: La Quinta Inn & Suites Chicago Downtown Fr $196+/Nt
Expedia
$123 Chicago, Illinois Chicago Savings! Book at Holiday Inn Chicago O'Hare Fr $123+/Nt
Expedia
$243 Chicago, Illinois Book 3 Nts in Chicago this Aug Fr $243+/Nt
Expedia
$316 Chicago, Illinois Save in Chicago: Book 3 Nts in Aug Fr $316+/Nt
Expedia
$199 Chicago, Illinois Aug deal: Chicago Marriott at Medical District/UIC Fr $199+/Nt
Expedia
$846 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $846
Expedia
$252 Chicago, Illinois Save in Chicago: Book 3 Nts in Aug at Omni Chicago Fr $252+/Nt
Save with Expedia, $27/night less
$156 Chicago, Illinois Save Big This Aug! Book 3 Nts in Chicago Fr $156+/Nt
Expedia
$159 Chicago, Illinois Chicago Savings! Book at The Drake Fr $159+/Nt
Expedia
$169 Chicago, Illinois Save Big This Aug! Book 3 Nts in Chicago Fr $169+/Nt
Expedia
$189 Chicago, Illinois Small budget: Stay in Chicago this Aug Fr $189+/Nt
Expedia
$157 Chicago, Illinois Aug deal: Crowne Plaza Chicago Magnificent Mile Fr $157+/Nt
Expedia
$169 Chicago, Illinois Book in Chicago: Save this Aug Fr $169+/Nt
Expedia
$119 Chicago, Illinois Book 3.5-Star Hilton Suites Chicago/Magnificent Mile Fr $119+/Nt
Expedia
$142 Chicago, Illinois Chicago Savings! Book 3 Nts in Aug Fr $142+/Nt
Expedia
$753 Chicago, Illinois 3.5-Star Chicago Sale! 3 Nts + Air Fr $753
Expedia
$262 Chicago, Illinois Special deal: 4-Star Sheraton Chicago and Towers Fr $262+/Nt
Expedia
$264 Chicago, Illinois The Ritz-Carlton Chicago (A Four Seasons ) in Aug: $264 & Up
Save with Expedia, $131/night less
$169 Chicago, Illinois Book 4-Star dana and spa in Chicago Fr $169+/Nt
Expedia
$105 Chicago, Illinois Chicago Savings! Book 3 Nts in Aug Fr $105+/Nt
Save with Expedia, $11/night less
$100 Chicago, Illinois Chicago Savings! Book 3 Nts in Aug Fr $100+/Nt
Expedia
$568 Chicago, Illinois Chicago 3.5-Star Hotel Sale! 3 Nts + Air Fr $568
Expedia
$1,752 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $1,752
Expedia
$96 Chicago, Illinois BEST WESTERN Grant Park in Aug: $96 & Up
Save with Expedia, $24/night less
$139 Evanston, Illinois Save Big This Aug! Book 3 Nts in Evanston Fr $139+/Nt
Expedia
$102 Lisle, Illinois Book 3.5-Star Sheraton Lisle in Lisle Fr $102+/Nt
Expedia
PRICEDESTINATIONDEAL
$305 Newark, New Jersey Cheap Flights from Dallas
DealBase.com
$205 Newark, New Jersey Cheap Flights from Tampa
DealBase.com
$97 Newark, New Jersey Cheap Flights from Boston
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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