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
$228 Chicago, Illinois United Airlines Weekend Specials for 10/24/14
DealBase.com
$85+ Chicago, Illinois 4-Star Chicago Hotels from $85
trivago
$93 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $93+/Nt
Save with Expedia, $16/night less
$228 Chicago, Illinois United Airlines Weekend Specials for 10/24/14
DealBase.com
$72 Chicago, Illinois Oct deal: The Tremont Chicago at Magnificent Mile Fr $72+/Nt
Expedia
$112+ Chicago, Illinois 4.5 Star Luxury Chicago Hotel on Sale! Starting from $112/nt
Jetsetter
$113 Chicago, Illinois $113 & Up: The Palmer House Hilton 4-Star Hotel in Chicago
Expedia
$125+ Chicago, Illinois Chicago on Sale! Starting From $125/nt
Jetsetter
$522 Chicago, Illinois Great Rates in Chicago + Breakfast!
DealBase.com
$143 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $143+/Nt
Expedia
$39 Chicago, Illinois Frontier Airlines Time to Fly Sale
DealBase.com
$876 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $876
Expedia
$278 Chicago, Illinois United Airlines Weekend Specials for 10/24/14
DealBase.com
$839 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $839
Expedia
$164 Chicago, Illinois Southwest Airlines Cozy Up to Winter Deals
DealBase.com
$136 Chicago, Illinois Save at 4-Star Raffaello: $136 & Up in Oct
Save with Expedia, $73/night less
$157 Chicago, Illinois Southwest Airlines Cozy Up to Winter Deals
DealBase.com
$140 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $140+/Nt
Expedia
$129 Chicago, Illinois Southwest Airlines Cozy Up to Winter Deals
DealBase.com
$1,366 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $1,366
Expedia
$129 Chicago, Illinois Southwest Airlines Cozy Up to Winter Deals
DealBase.com
$583 Chicago, Illinois Chicago 3.5-Star Hotel Sale! 3 Nts + Air Fr $583
Expedia
$278 Chicago, Illinois United Airlines Weekend Specials for 10/24/14
DealBase.com
$195 Chicago, Illinois The James Chicago on Sale: Book 3 Nts in Oct Fr $195+/Nt
Save with Expedia, $34/night less
$107 Chicago, Illinois Southwest Airlines Cozy Up to Winter Deals
DealBase.com
$158 Chicago, Illinois Book 4-Star The Westin Chicago River North Fr $158+/Nt
Expedia
$110 Chicago, Illinois Southwest Airlines Cozy Up to Winter Deals
DealBase.com
$106 Chicago, Illinois Book in Chicago: Save this Oct Fr $106+/Nt
Expedia
$138 Chicago, Illinois Chicago Savings! Book at W Chicago Lakeshore Fr $138+/Nt
Expedia
$167 Chicago, Illinois Oct deal: Holiday Inn Chicago Mart Plaza River North Fr $167+/Nt
Expedia
$375 Chicago, Illinois Chicago 3.5-Star Hotel Sale! 3 Nts + Air Fr $375
Expedia
$99 Chicago, Illinois Chicago Savings! Book at Chicago South Loop Fr $99+/Nt
Expedia
$109 Chicago, Illinois Blake Chicago in Oct: $109 & Up
Expedia
$102 Chicago, Illinois Oct deal: Millennium Knickerbocker Chicago Fr $102+/Nt
Save with Expedia, $17/night less
$176 Chicago, Illinois Book in Chicago: Save this Oct Fr $176+/Nt
Expedia
$199 Chicago, Illinois Oct deal: Hyatt Regency Chicago Fr $199+/Nt
Expedia
$121 Chicago, Illinois Oct deal: The Westin Michigan Avenue Chicago Fr $121+/Nt
Expedia
$179 Chicago, Illinois Courtyard Chicago Downtown/Magnificent Mile in Oct: $179 & Up
Expedia
$815 Chicago, Illinois 3.5-Star Chicago Sale! 3 Nts + Air Fr $815
Expedia
$1,584 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $1,584
Expedia
$116 Chicago, Illinois Save Big This Oct! Book 3 Nts at Central Loop Fr $116+/Nt
Expedia
$156 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $156+/Nt
Expedia
$206 Chicago, Illinois Special deal: 3.5-Star Kinzie Fr $206+/Nt
Expedia
$133 Chicago, Illinois Oct deal: Homewood Suites by Hilton Chicago Downtown Fr $133+/Nt
Expedia
$726 Chicago, Illinois 3.5-Star Chicago Sale! 3 Nts + Air Fr $726
Expedia
$256 Chicago, Illinois Special deal: 3.5-Star Buckingham Athletic Club Fr $256+/Nt
Expedia
$138 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $138+/Nt
Expedia
$344 Chicago, Illinois Chicago Savings! Book at Waldorf Astoria Chicago Fr $344+/Nt
Expedia
$109 Chicago, Illinois Crowne Plaza Chicago - The Metro in Oct: $109 & Up
Expedia
$148 Chicago, Illinois Oct deal: Hampton Inn & Suites Chicago - Downtown Fr $148+/Nt
Expedia
$159 Chicago, Illinois Save Big This Oct! Book 3 Nts at Renaissance Chicago Fr $159+/Nt
Expedia
$116 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $116+/Nt
Save with Expedia, $21/night less
$209 Chicago, Illinois Special deal: 4.5-Star Conrad Chicago Fr $209+/Nt
Expedia
$179 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $179+/Nt
Expedia
$123 Chicago, Illinois Book in Chicago: Save this Oct Fr $123+/Nt
Expedia
$119 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $119+/Nt
Save with Expedia, $30/night less
$115 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $115+/Nt
Expedia
$392 Chicago, Illinois Book the Four Seasons Chicago 3 Nts in Oct Fr $392+/Nt
Save with Expedia, $43/night less
$176 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $176+/Nt
Save with Expedia, $43/night less
$128 Chicago, Illinois Omni Chicago on Sale: Book 3 Nts in Oct Fr $128+/Nt
Save with Expedia, $31/night less
$152 Chicago, Illinois Chicago Savings! Book at Holiday Inn Chicago Downtown Fr $152+/Nt
Expedia
$152 Chicago, Illinois Oct deal: Embassy Suites Chicago Downtown Fr $152+/Nt
Expedia
$100 Chicago, Illinois BEST WESTERN River North on Sale: Book 3 Nts in Oct Fr $100+/Nt
Expedia
$112 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $112+/Nt
Expedia
$336 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $336+/Nt
Save with Expedia, $60/night less
$79 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $79+/Nt
Expedia
$121 Chicago, Illinois Monaco Chicago - a Kimpton in Oct: $121 & Up
Save with Expedia, $52/night less
$149 Chicago, Illinois Embassy Suites Chicago Downtown Lakefront in Oct: $149 & Up
Expedia
$88 Chicago, Illinois Special deal: 4.5-Star InterContinental Chicago Fr $88+/Nt
Expedia
$144 Chicago, Illinois Fairmont Chicago Millennium Park in Oct: $144 & Up
Save with Expedia, $15/night less
$188 Chicago, Illinois Chicago Savings! Book at The Blackstone A Renaissance Fr $188+/Nt
Expedia
$135 Chicago, Illinois Save at 3-Star Congress Plaza: $135 & Up in Oct
Expedia
$179 Chicago, Illinois Save at 4-Star The Drake: $179 & Up in Oct
Expedia
$260 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $260+/Nt
Expedia
$135 Chicago, Illinois Chicago Savings! Book at Holiday Inn Chicago O'Hare Fr $135+/Nt
Expedia
$124 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $124+/Nt
Expedia
$99 Chicago, Illinois $99 & Up: Comfort Suites Michigan Avenue 3-Star Hotel in Chicago
Expedia
$81 Chicago, Illinois River on Sale: Book 3 Nts in Oct Fr $81+/Nt
Save with Expedia, $8/night less
$127 Chicago, Illinois Chicago Savings! Book at Burnham - a Kimpton Fr $127+/Nt
Save with Expedia, $22/night less
$179 Chicago, Illinois Chicago Savings! Book at JW Marriott Chicago Fr $179+/Nt
Expedia
$110 Chicago, Illinois Book 3-Star ACME Company Chicago in Chicago Fr $110+/Nt
Save with Expedia, $19/night less
$166 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $166+/Nt
Expedia
$129 Chicago, Illinois Book in Chicago: Save this Oct Fr $129+/Nt
Expedia
$119 Chicago, Illinois Palomar Chicago, a Kimpton in Oct: $119 & Up
Save with Expedia, $20/night less
$115 Chicago, Illinois Book 4-Star theWit - A DoubleTree by Hilton Fr $115+/Nt
Expedia
$96 Chicago, Illinois Book 3.5-Star Club Quarters Chicago - Central Loop Fr $96+/Nt
Expedia
$109 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $109+/Nt
Expedia
$125 Chicago, Illinois $125 & Up: Warwick Allerton Chicago 4-Star Hotel in Chicago
Save with Expedia, $59/night less
$103 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $103+/Nt
Expedia
$116 Chicago, Illinois Oct deal: Chicago Marriott at Medical District/UIC Fr $116+/Nt
Expedia
$183 Chicago, Illinois Oct deal: Residence Inn Chicago Downtown Fr $183+/Nt
Expedia
$139 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $139+/Nt
Expedia
$156 Chicago, Illinois Chicago Savings! Book at Sofitel Chicago Water Tower Fr $156+/Nt
Expedia
$166 Chicago, Illinois Book the dana and spa 3 Nts in Oct Fr $166+/Nt
Expedia
$129 Chicago, Illinois Save at 4-Star MileNorth, A Chicago: $129 & Up in Oct
Expedia
$94 Chicago, Illinois Oct deal: Travelodge Chicago Downtown Fr $94+/Nt
Expedia
$317 Chicago, Illinois Chicago Savings! Book at The Peninsula Chicago Fr $317+/Nt
Save with Expedia, $158/night less
$103 Chicago, Illinois Oct deal: Hilton Chicago Fr $103+/Nt
Expedia
$149 Chicago, Illinois Save at 4-Star Hyatt Chicago Magnificent Mile: $149 & Up in Oct
Expedia
$127 Chicago, Illinois Oct deal: Hard Rock Chicago Fr $127+/Nt
Save with Expedia, $22/night less
PRICEDESTINATIONDEAL
$149 New York City, New York Cheap Flights from Washington, DC
DealBase.com
$212 New York City, New York Cheap Flights from Raleigh
DealBase.com
$177 New York City, New York Cheap Flights from Dallas
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