Sign up for weekly Top Travel Deals! view sample

Chicago, IL Travel Deals

left end graphic
Find Travel Deals
deals tag right end graphic

Chicago, IL Travel Deals

Show:
TYPE PRICE DESTINATION DEAL
$119 Chicago, Illinois Special deal: 4-Star The Palmer House Hilton Fr $119+/Nt
Expedia
$184 Chicago, Illinois Virgin America Low Fares
DealBase.com
$1,686 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $1,686
Expedia
$218 Chicago, Illinois Southwest Airlines Mexico and Caribbean Sale
DealBase.com
$1,196 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $1,196
Expedia
$229 Chicago, Illinois Southwest Airlines Mexico and Caribbean Sale
DealBase.com
$171 Chicago, Illinois Chicago Savings! Book at BEST WESTERN Grant Park Fr $171+/Nt
Save with Expedia, $19/night less
$251 Chicago, Illinois Southwest Airlines Mexico and Caribbean Sale
DealBase.com
$226 Chicago, Illinois Save Big This May! Book 3 Nts in Chicago Fr $226+/Nt
Save with Expedia, $40/night less
$200 Chicago, Illinois Virgin America Low Fares
DealBase.com
$176 Chicago, Illinois May deal: Hampton Majestic Chicago Theatre District Fr $176+/Nt
Expedia
$200 Chicago, Illinois Virgin America Low Fares
DealBase.com
$149 Chicago, Illinois Save in Chicago: Book 3 Nts in May Fr $149+/Nt
Expedia
$89+ Chicago, Illinois Chicago Hotel Deals For As Low As $89/nt!
Jetsetter
$161 Chicago, Illinois Hard Rock Chicago in May: $161 & Up
Save with Expedia, $28/night less
$59 Chicago, Illinois Frontier Airlines Travel Deals
DealBase.com
$945 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $945
Expedia
$200 Chicago, Illinois Virgin America Low Fares
DealBase.com
$234 Chicago, Illinois Chicago Savings! Book at Sofitel Chicago Water Tower Fr $234+/Nt
Expedia
$180 Chicago, Illinois Virgin America Low Fares
DealBase.com
$395 Chicago, Illinois Chicago Savings! Book 3 Nts in May Fr $395+/Nt
Expedia
$200 Chicago, Illinois Virgin America Low Fares
DealBase.com
$184 Chicago, Illinois Chicago Savings! Book 3 Nts in May Fr $184+/Nt
Expedia
$104 Chicago, Illinois Special deal: 4-Star Millennium Knickerbocker Chicago Fr $104+/Nt
Expedia
$257 Chicago, Illinois Chicago Savings! Book 3 Nts in May Fr $257+/Nt
Expedia
$225 Chicago, Illinois Book in Chicago: Save this May Fr $225+/Nt
Save with Expedia, $24/night less
$154 Chicago, Illinois Small budget: Stay in Chicago this May Fr $154+/Nt
Expedia
$98 Chicago, Illinois Red Roof Inn Chicago Downtown Magnificent Mile in May: $98 & Up
Save with Expedia, $32/night less
$732 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $732
Expedia
$237 Chicago, Illinois Chicago Savings! Book 3 Nts in May Fr $237+/Nt
Save with Expedia, $26/night less
$259 Chicago, Illinois Save Big This May! Book 3 Nts in Chicago Fr $259+/Nt
Expedia
$217 Chicago, Illinois Book 4.5-Star The James Chicago Fr $217+/Nt
Save with Expedia, $92/night less
$119 Chicago, Illinois Save in Chicago: Book 3 Nts in May at The Whitehall Fr $119+/Nt
Save with Expedia, $39/night less
$215 Chicago, Illinois Small budget: Stay in Chicago this May Fr $215+/Nt
Expedia
$119 Chicago, Illinois Small budget: Book MileNorth, A Chicago 3 Nts in May Fr $119+/Nt
Expedia
$159 Chicago, Illinois Book the BEST WESTERN River North 3 Nts in May Fr $159+/Nt
Expedia
$1,544 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $1,544
Expedia
$133 Chicago, Illinois Book 3-Star La Quinta Inn & Suites Chicago Downtown Fr $133+/Nt
Expedia
$198 Chicago, Illinois Special deal: 4-Star Fairmont Chicago Millennium Park Fr $198+/Nt
Save with Expedia, $35/night less
$179 Chicago, Illinois Book 3.5-Star Courtyard Chicago Downtown River North Fr $179+/Nt
Expedia
$169 Chicago, Illinois Book 3 Nts in Chicago this May Fr $169+/Nt
Expedia
$113 Chicago, Illinois Chicago's Essex Inn in May: $113 & Up
Save with Expedia, $20/night less
$1,531 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $1,531
Expedia
$139 Chicago, Illinois Special deal: 3-Star Chicago South Loop Fr $139+/Nt
Expedia
$173 Chicago, Illinois Book the Hilton Chicago O'Hare Airport 3 Nts in May Fr $173+/Nt
Expedia
$529 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $529
Expedia
$237 Chicago, Illinois Save Big This May! Book 3 Nts at Renaissance Chicago Fr $237+/Nt
Expedia
$136 Chicago, Illinois Book in Chicago: Save at the Felix in May Fr $136+/Nt
Save with Expedia, $24/night less
$276 Chicago, Illinois Chicago Savings! Book at W Chicago - City Center Fr $276+/Nt
Expedia
$219 Chicago, Illinois Save at 3-Star Rush: $219 & Up in May
Expedia
$196 Chicago, Illinois Book the Palomar Chicago, a Kimpton 3 Nts in May Fr $196+/Nt
Expedia
$194 Chicago, Illinois Book 3 Nts in Chicago this May Fr $194+/Nt
Expedia
$218 Chicago, Illinois Book the The Blackstone A Renaissance 3 Nts in May Fr $218+/Nt
Expedia
$170 Chicago, Illinois Save at 4-Star dana and spa: $170 & Up in May
Save with Expedia, $29/night less
$112 Chicago, Illinois Book in Chicago: Save at the Central Loop in May Fr $112+/Nt
Save with Expedia, $27/night less
$120 Chicago, Illinois Save Big This May! Book 3 Nts in Chicago Fr $120+/Nt
Expedia
$197 Chicago, Illinois Save at 4-Star Sheraton Chicago and Towers: $197 & Up in May
Expedia
$172 Chicago, Illinois May deal: Chicago Downtown, Autograph Collection Fr $172+/Nt
Expedia
$199 Chicago, Illinois Book 3 Nts in Chicago this May Fr $199+/Nt
Expedia
$152 Chicago, Illinois Warwick Allerton Chicago on Sale: Book 3 Nts in May Fr $152+/Nt
Expedia
$156 Chicago, Illinois Chicago Savings! Book at Holiday Inn Chicago Downtown Fr $156+/Nt
Expedia
$220 Chicago, Illinois Save at 4.5-Star Radisson Blu Aqua: $220 & Up in May
Expedia
$144 Chicago, Illinois Small budget: Stay in Chicago this May Fr $144+/Nt
Expedia
$149 Chicago, Illinois Small budget: Book Congress Plaza 3 Nts in May Fr $149+/Nt
Expedia
$108 Chicago, Illinois Book the River 3 Nts in May Fr $108+/Nt
Save with Expedia, $15/night less
$224 Chicago, Illinois Book in Chicago: Save at the Hilton Chicago in May Fr $224+/Nt
Expedia
$1,125 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $1,125
Expedia
$209 Chicago, Illinois Book in Chicago: Save this May Fr $209+/Nt
Expedia
$316 Chicago, Illinois Save at 4-Star JW Marriott Chicago: $316 & Up in May
Expedia
$199 Chicago, Illinois Chicago Savings! Book at The Drake Fr $199+/Nt
Expedia
$106 Chicago, Illinois May deal: Club Quarters, Central Loop Fr $106+/Nt
Save with Expedia, $27/night less
$189 Chicago, Illinois Save Big This May! Book 3 Nts in Chicago Fr $189+/Nt
Expedia
$189 Chicago, Illinois Special deal: 4-Star theWit - A DoubleTree by Hilton Fr $189+/Nt
Expedia
$183 Chicago, Illinois Small budget: Stay in Chicago this May Fr $183+/Nt
Expedia
$146 Chicago, Illinois Small budget: Stay in Chicago this May Fr $146+/Nt
Expedia
$1,433 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $1,433
Expedia
$133 Chicago, Illinois Chicago Savings! Book 3 Nts in May Fr $133+/Nt
Expedia
$199 Chicago, Illinois Hampton Inn & Suites Chicago - Downtown in May: $199 & Up
Expedia
$213 Chicago, Illinois Book 3.5-Star Embassy Suites Chicago Downtown Fr $213+/Nt
Expedia
$343 Chicago, Illinois Book 5-Star Trump International & Tower Chicago Fr $343+/Nt
Save with Expedia, $86/night less
$405 Chicago, Illinois $405 & Up: Four Seasons Chicago 5-Star Hotel in Chicago
Expedia
$229 Chicago, Illinois Save Big This May! Book 3 Nts in Chicago Fr $229+/Nt
Expedia
$169 Chicago, Illinois Book the Comfort Suites Michigan Avenue 3 Nts in May Fr $169+/Nt
Expedia
$192 Chicago, Illinois Book 4.5-Star Omni Chicago in Chicago Fr $192+/Nt
Save with Expedia, $47/night less
$190 Chicago, Illinois Save in Chicago: Book 3 Nts in May Fr $190+/Nt
Expedia
$130 Chicago, Illinois Chicago Savings! Book 3 Nts in May Fr $130+/Nt
Expedia
$525 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $525
Expedia
$190 Chicago, Illinois Book in Chicago: Save this May Fr $190+/Nt
Expedia
$1,223 Chicago, Illinois Chicago 3.5-Star Hotel Sale! 3 Nts + Air Fr $1,223
Expedia
$226 Chicago, Illinois Chicago Savings! Book at InterContinental Chicago Fr $226+/Nt
Expedia
$851 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $851
Expedia
$499 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $499
Expedia
$175 Chicago, Illinois Crowne Plaza Chicago - The Metro in May: $175 & Up
Expedia
$167 Chicago, Illinois Chicago Savings! Book at ACME Company Chicago Fr $167+/Nt
Save with Expedia, $29/night less
$169 Chicago, Illinois Special deal: 4-Star PUBLIC Chicago Fr $169+/Nt
Expedia
$290 Chicago, Illinois May deal: The Ritz-Carlton Chicago (A Four Seasons ) Fr $290+/Nt
Save with Expedia, $145/night less
$183 Chicago, Illinois $183 & Up: Kinzie 3.5-Star Hotel in Chicago
Expedia
$739 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $739
Expedia
$84 Chicago, Illinois Hostelling International Chicago in May: $84 & Up
Expedia
$549 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $549
Expedia
PRICEDESTINATIONDEAL
$79 Philadelphia, Pennsylvania Frontier Airlines Travel Deals
DealBase.com
$49 Philadelphia, Pennsylvania Frontier Airlines Travel Deals
DealBase.com
$389 Philadelphia, Pennsylvania Cheap Flights from Los Angeles
DealBase.com
FREE! Weekly Travel Deals Newsletter

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.
left end graphic
Find Travel Deals
right end graphic
bookingbuddy_com deals bookingbuddy.com http://rd.BookingBuddy.com/?loc1=30246&slocation1=239826&ucid=30246&ad_user_tracking=%5Bsource%3D%2Ctaparam%3D%2Csupmt%3D%5D 17866