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
$162 Chicago, Illinois Southwest Airlines Grab Your Favorite Seat Sale
DealBase.com
$17 Chicago, Illinois Cheap Car Rentals in Chicago Fr $17/Day
CarRentals.com
$278 Chicago, Illinois United Airlines Weekend Specials for 10/24/14
DealBase.com
$68 Chicago, Illinois Book in Chicago: Save this Oct Fr $68+/Nt
Expedia
$268 Chicago, Illinois American Airlines Domestic Getaways for Next Weekend - 10/31/14
DealBase.com
$494 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $494
Expedia
$230 Chicago, Illinois American Airlines Domestic Getaways for Next Weekend - 10/31/14
DealBase.com
$112+ Chicago, Illinois 4.5 Star Luxury Chicago Hotel on Sale! Starting from $112/nt
Jetsetter
$133 Chicago, Illinois United Airlines US Fare Sale
DealBase.com
$129 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $129+/Nt
Expedia
$228 Chicago, Illinois United Airlines Weekend Specials for 10/24/14
DealBase.com
$125+ Chicago, Illinois Chicago on Sale! Starting From $125/nt
Jetsetter
$522 Chicago, Illinois Great Rates in Chicago + Breakfast!
DealBase.com
$113 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $113+/Nt
Expedia
$278 Chicago, Illinois United Airlines Weekend Specials for 10/24/14
DealBase.com
$130 Chicago, Illinois Save at 4-Star The Westin Chicago River North: $130 & Up in Oct
Expedia
$253 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$123 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $123+/Nt
Expedia
$310 Chicago, Illinois American Airlines Domestic Getaways for Next Weekend - 10/31/14
DealBase.com
$884 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $884
Expedia
$134 Chicago, Illinois Southwest Airlines Grab Your Favorite Seat Sale
DealBase.com
$203 Chicago, Illinois Renaissance Chicago in Oct: $203 & Up
Expedia
$169 Chicago, Illinois Southwest Airlines Grab Your Favorite Seat Sale
DealBase.com
$718 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $718
Expedia
$310 Chicago, Illinois American Airlines Domestic Getaways for Next Weekend - 10/31/14
DealBase.com
$260 Chicago, Illinois Chicago Savings! Book at Park Hyatt Chicago Fr $260+/Nt
Expedia
$267 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$130 Chicago, Illinois Save Big This Oct! Book 3 Nts at W Chicago Lakeshore Fr $130+/Nt
Expedia
$245 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$144 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $144+/Nt
Save with Expedia, $15/night less
$197 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$102 Chicago, Illinois Save at 4-Star Millennium Knickerbocker Chicago: $102 & Up in Oct
Save with Expedia, $17/night less
$115 Chicago, Illinois Southwest Airlines Grab Your Favorite Seat Sale
DealBase.com
$159 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct at Conrad Chicago Fr $159+/Nt
Expedia
$112 Chicago, Illinois Southwest Airlines Grab Your Favorite Seat Sale
DealBase.com
$128 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $128+/Nt
Expedia
$197 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$188 Chicago, Illinois Book in Chicago: Save this Oct Fr $188+/Nt
Expedia
$134 Chicago, Illinois Southwest Airlines Grab Your Favorite Seat Sale
DealBase.com
$1,134 Chicago, Illinois 3.5-Star Chicago Sale! 3 Nts + Air Fr $1,134
Expedia
$87 Chicago, Illinois Oct deal: Indigo Chicago Downtown Gold Coast Fr $87+/Nt
Expedia
$109 Chicago, Illinois Holiday Inn Express Cass on Sale: Book 3 Nts in Oct Fr $109+/Nt
Expedia
$670 Chicago, Illinois 3.5-Star Chicago Sale! 3 Nts + Air Fr $670
Expedia
$135 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $135+/Nt
Expedia
$130 Chicago, Illinois Book 3-Star Holiday Inn Chicago O'Hare in Chicago Fr $130+/Nt
Expedia
$123 Chicago, Illinois Doubletree by Hilton Chicago Magnificent Mile in Oct: $123 & Up
Expedia
$161 Chicago, Illinois Crowne Plaza Chicago Magnificent Mile in Oct: $161 & Up
Expedia
$159 Chicago, Illinois Oct deal: The Drake Fr $159+/Nt
Expedia
$370 Chicago, Illinois The Peninsula Chicago in Oct: $370 & Up
Save with Expedia, $185/night less
$1,296 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $1,296
Expedia
$115 Chicago, Illinois Small budget: Book Days Inn Chicago 3 Nts in Oct Fr $115+/Nt
Expedia
$278 Chicago, Illinois Chicago Savings! Book at Waldorf Astoria Chicago Fr $278+/Nt
Expedia
$119 Chicago, Illinois Book 3-Star Hampton Inn & Suites Chicago - Downtown Fr $119+/Nt
Expedia
$179 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $179+/Nt
Expedia
$199 Chicago, Illinois Chicago Savings! Book at JW Marriott Chicago Fr $199+/Nt
Expedia
$82 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct at Blake Chicago Fr $82+/Nt
Save with Expedia, $27/night less
$149 Chicago, Illinois Chicago Savings! Book at Kinzie Fr $149+/Nt
Expedia
$130 Chicago, Illinois Book in Chicago: Save this Oct Fr $130+/Nt
Expedia
$149 Chicago, Illinois dana and spa in Oct: $149 & Up
Expedia
$99 Chicago, Illinois Chicago Savings! Book at BEST WESTERN Grant Park Fr $99+/Nt
Save with Expedia, $25/night less
$128 Chicago, Illinois Book 3.5-Star Hilton Suites Chicago/Magnificent Mile Fr $128+/Nt
Expedia
$166 Chicago, Illinois Hampton Majestic Chicago Theatre District in Oct: $166 & Up
Expedia
$161 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $161+/Nt
Save with Expedia, $69/night less
$119 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $119+/Nt
Expedia
$336 Chicago, Illinois The Ritz-Carlton Chicago (A Four Seasons ) in Oct: $336 & Up
Save with Expedia, $60/night less
$110 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $110+/Nt
Expedia
$112 Chicago, Illinois Book in Chicago: Save this Oct Fr $112+/Nt
Save with Expedia, $7/night less
$103 Chicago, Illinois Save Big This Oct! Book 3 Nts at Hilton Chicago Fr $103+/Nt
Expedia
$114 Chicago, Illinois Oct deal: BEST WESTERN River North Fr $114+/Nt
Expedia
$94 Chicago, Illinois Hyatt Regency Chicago in Oct: $94 & Up
Expedia
$99 Chicago, Illinois Chicago Savings! Book at Chicago South Loop Fr $99+/Nt
Expedia
$266 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $266+/Nt
Save with Expedia, $67/night less
$173 Chicago, Illinois Oct deal: Chicago's Essex Inn Fr $173+/Nt
Expedia
$110 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $110+/Nt
Expedia
$126 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $126+/Nt
Expedia
$146 Chicago, Illinois Book 4-Star Chicago Downtown, Autograph Collection Fr $146+/Nt
Save with Expedia, $37/night less
$109 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $109+/Nt
Expedia
$170 Chicago, Illinois Chicago Savings! Book at The Silversmith Fr $170+/Nt
Save with Expedia, $29/night less
$136 Chicago, Illinois Book in Chicago: Save this Oct Fr $136+/Nt
Expedia
$127 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $127+/Nt
Save with Expedia, $22/night less
$78 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct at Congress Plaza Fr $78+/Nt
Expedia
$95 Chicago, Illinois Oct deal: Homewood Suites by Hilton Chicago Downtown Fr $95+/Nt
Expedia
$156 Chicago, Illinois Book the Sofitel Chicago Water Tower 3 Nts in Oct Fr $156+/Nt
Expedia
$149 Chicago, Illinois Book 4-Star Hyatt Chicago Magnificent Mile in Chicago Fr $149+/Nt
Expedia
$171 Chicago, Illinois Special deal: 4-Star Swissotel Chicago Fr $171+/Nt
Save with Expedia, $42/night less
$128 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct at Omni Chicago Fr $128+/Nt
Save with Expedia, $31/night less
$96 Chicago, Illinois Club Quarters Chicago - Central Loop in Oct: $96 & Up
Save with Expedia, $10/night less
$256 Chicago, Illinois Book 3.5-Star Buckingham Athletic Club Fr $256+/Nt
Expedia
$173 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $173+/Nt
Expedia
$125 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $125+/Nt
Save with Expedia, $59/night less
$110 Chicago, Illinois Small budget: Book ACME Company Chicago 3 Nts in Oct Fr $110+/Nt
Save with Expedia, $19/night less
$110 Chicago, Illinois Chicago Savings! Book at Burnham - a Kimpton Fr $110+/Nt
Save with Expedia, $19/night less
$912 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $912
Expedia
$138 Chicago, Illinois Save Big This Oct! Book 3 Nts at Radisson Blu Aqua Fr $138+/Nt
Expedia
$128 Chicago, Illinois Special deal: 4.5-Star InterContinental Chicago Fr $128+/Nt
Expedia
$115 Chicago, Illinois Special deal: 4-Star theWit - A DoubleTree by Hilton Fr $115+/Nt
Expedia
$194 Chicago, Illinois Holiday Inn Express Chicago-Midway Airport in Oct: $194 & Up
Expedia
$167 Chicago, Illinois Chicago Savings! Book at The James Chicago Fr $167+/Nt
Save with Expedia, $29/night less
PRICEDESTINATIONDEAL
$149 New York City, New York Cheap Flights from Washington, DC
DealBase.com
$177 New York City, New York Cheap Flights from Chicago
DealBase.com
$193 New York City, New York Cheap Flights from Tampa
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