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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$253 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$91 Chicago, Illinois Chicago Savings! Book at Warwick Allerton Chicago Fr $91+/Nt
Save with Expedia, $73/night less
$280 Chicago, Illinois American Airlines Domestic Getaways for This Weekend - 10/31/14
DealBase.com
$94 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $94+/Nt
Expedia
$270 Chicago, Illinois US Airways Domestic e-Saver Specials for 11/1/14
DealBase.com
$87 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $87+/Nt
Expedia
$169 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$137 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $137+/Nt
Save with Expedia, $24/night less
$200 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$144 Chicago, Illinois Special deal: 4-Star Fairmont Chicago Millennium Park Fr $144+/Nt
Save with Expedia, $15/night less
$125+ Chicago, Illinois Chicago on Sale! Starting From $125/nt
Jetsetter
$114 Chicago, Illinois Book in Chicago: Save this Oct Fr $114+/Nt
Expedia
$133 Chicago, Illinois United Airlines US Fare Sale
DealBase.com
$123 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $123+/Nt
Expedia
$278 Chicago, Illinois United Airlines Weekend Specials for 10/31/14
DealBase.com
$123 Chicago, Illinois Chicago Savings! Book at Buckingham Athletic Club Fr $123+/Nt
Expedia
$17 Chicago, Illinois Cheap Car Rentals in Chicago Fr $17/Day
CarRentals.com
$264 Chicago, Illinois Oct deal: The Ritz-Carlton Chicago (A Four Seasons ) Fr $264+/Nt
Save with Expedia, $131/night less
$228 Chicago, Illinois United Airlines Weekend Specials for 10/31/14
DealBase.com
$260 Chicago, Illinois Park Hyatt Chicago on Sale: Book 3 Nts in Oct Fr $260+/Nt
Expedia
$200 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$661 Chicago, Illinois Chicago 3.5-Star Hotel Sale! 3 Nts + Air Fr $661
Expedia
$134 Chicago, Illinois Southwest Airlines Grab Your Favorite Seat Sale
DealBase.com
$550 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $550
Expedia
$169 Chicago, Illinois Southwest Airlines Grab Your Favorite Seat Sale
DealBase.com
$128 Chicago, Illinois Oct deal: Courtyard Chicago Downtown/Magnificent Mile Fr $128+/Nt
Expedia
$310 Chicago, Illinois American Airlines Domestic Getaways for This Weekend - 10/31/14
DealBase.com
$159 Chicago, Illinois Special deal: 4.5-Star Conrad Chicago Fr $159+/Nt
Expedia
$112+ Chicago, Illinois 4.5 Star Luxury Chicago Hotel on Sale! Starting from $112/nt
Jetsetter
$668 Chicago, Illinois Chicago 3.5-Star Hotel Sale! 3 Nts + Air Fr $668
Expedia
$280 Chicago, Illinois American Airlines Domestic Getaways for This Weekend - 10/31/14
DealBase.com
$85 Chicago, Illinois Crowne Plaza Chicago Magnificent Mile in Oct: $85 & Up
Expedia
$245 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$110 Chicago, Illinois $110 & Up: Hard Rock Chicago 4-Star Hotel in Chicago
Save with Expedia, $19/night less
$175 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$278 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $278+/Nt
Expedia
$197 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$102 Chicago, Illinois Book 3-Star Hampton Inn & Suites Chicago - Downtown Fr $102+/Nt
Expedia
$200 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$113 Chicago, Illinois Chicago Savings! Book at Hilton Chicago Fr $113+/Nt
Expedia
$115 Chicago, Illinois Southwest Airlines Grab Your Favorite Seat Sale
DealBase.com
$135 Chicago, Illinois Book 4.5-Star InterContinental Chicago in Chicago Fr $135+/Nt
Expedia
$162 Chicago, Illinois Southwest Airlines Grab Your Favorite Seat Sale
DealBase.com
$115 Chicago, Illinois Chicago Savings! Book at Days Inn Chicago Fr $115+/Nt
Expedia
$112 Chicago, Illinois Southwest Airlines Grab Your Favorite Seat Sale
DealBase.com
$100 Chicago, Illinois Book 4-Star The Westin Michigan Avenue Chicago Fr $100+/Nt
Expedia
$85+ Chicago, Illinois 4-Star Chicago Hotels from $85
trivago
$129 Chicago, Illinois Residence Inn Chicago Downtown in Oct: $129 & Up
Expedia
$13 Chicago, Illinois Cheap Car Rentals in Chicago Fr $13/Day
CarRentals.com
$149 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $149+/Nt
Expedia
$200 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$139 Chicago, Illinois Book 4-Star Millennium Knickerbocker Chicago Fr $139+/Nt
Save with Expedia, $25/night less
$44 Chicago, Illinois Sun Country Airlines December to Remember Sale
DealBase.com
$123 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct at Felix Fr $123+/Nt
Save with Expedia, $21/night less
$328 Chicago, Illinois United Airlines Weekend Specials for 10/31/14
DealBase.com
$96 Chicago, Illinois Chicago Savings! Book at The Palmer House Hilton Fr $96+/Nt
Expedia
$134 Chicago, Illinois Southwest Airlines Grab Your Favorite Seat Sale
DealBase.com
$128 Chicago, Illinois Small budget: Book Swissotel Chicago 3 Nts in Oct Fr $128+/Nt
Save with Expedia, $32/night less
$268 Chicago, Illinois American Airlines Domestic Getaways for This Weekend - 10/31/14
DealBase.com
$133 Chicago, Illinois Radisson Blu Aqua on Sale: Book 3 Nts in Oct Fr $133+/Nt
Expedia
$139 Chicago, Illinois Special deal: 4-Star The Drake Fr $139+/Nt
Expedia
$112 Chicago, Illinois Doubletree by Hilton Chicago Magnificent Mile in Oct: $112 & Up
Expedia
$129 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $129+/Nt
Expedia
$69 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $69+/Nt
Save with Expedia, $17/night less
$161 Chicago, Illinois Chicago Savings! Book at The James Chicago Fr $161+/Nt
Save with Expedia, $28/night less
$159 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $159+/Nt
Expedia
$93 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $93+/Nt
Expedia
$139 Chicago, Illinois The Westin Chicago River North in Oct: $139 & Up
Expedia
$865 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $865
Expedia
$119 Chicago, Illinois Comfort Suites Michigan Avenue in Oct: $119 & Up
Expedia
$99 Chicago, Illinois Oct deal: Club Quarters Chicago - Central Loop Fr $99+/Nt
Save with Expedia, $10/night less
$116 Chicago, Illinois Chicago Savings! Book at Sheraton Chicago and Towers Fr $116+/Nt
Expedia
$110 Chicago, Illinois Book in Chicago: Save this Oct Fr $110+/Nt
Expedia
$68 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $68+/Nt
Expedia
$161 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $161+/Nt
Expedia
$127 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $127+/Nt
Expedia
$140 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $140+/Nt
Save with Expedia, $59/night less
$153 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $153+/Nt
Expedia
$137 Chicago, Illinois Oct deal: Chicago Downtown, Autograph Collection Fr $137+/Nt
Save with Expedia, $46/night less
$317 Chicago, Illinois Chicago Savings! Book at The Peninsula Chicago Fr $317+/Nt
Save with Expedia, $158/night less
$77 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $77+/Nt
Expedia
$166 Chicago, Illinois Save Big This Oct! Book 3 Nts at Renaissance Chicago Fr $166+/Nt
Expedia
$660 Chicago, Illinois Chicago 3.5-Star Hotel Sale! 3 Nts + Air Fr $660
Expedia
$94 Chicago, Illinois Hyatt Regency Chicago in Oct: $94 & Up
Expedia
$108 Chicago, Illinois Homewood Suites by Hilton Chicago Downtown in Oct: $108 & Up
Expedia
$109 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $109+/Nt
Expedia
$127 Chicago, Illinois Book 4-Star Hyatt Chicago Magnificent Mile in Chicago Fr $127+/Nt
Expedia
$143 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $143+/Nt
Expedia
$290 Chicago, Illinois Book 5-Star Trump International & Tower Chicago Fr $290+/Nt
Save with Expedia, $72/night less
$126 Chicago, Illinois Chicago Savings! Book at MileNorth, A Chicago Fr $126+/Nt
Expedia
$99 Chicago, Illinois Save at 3-Star Chicago South Loop: $99 & Up in Oct
Expedia
$110 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $110+/Nt
Expedia
$126 Chicago, Illinois Book the Embassy Suites Chicago Downtown 3 Nts in Oct Fr $126+/Nt
Expedia
$109 Chicago, Illinois Crowne Plaza Chicago - The Metro in Oct: $109 & Up
Expedia
$166 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $166+/Nt
Expedia
$156 Chicago, Illinois Chicago Savings! Book at Sofitel Chicago Water Tower Fr $156+/Nt
Expedia
$128 Chicago, Illinois $128 & Up: Omni Chicago 4.5-Star Hotel in Chicago
Save with Expedia, $31/night less
$70 Chicago, Illinois Oct deal: The Tremont Chicago at Magnificent Mile Fr $70+/Nt
Expedia
$110 Chicago, Illinois Chicago Savings! Book at Burnham - a Kimpton Fr $110+/Nt
Save with Expedia, $19/night less
$110 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $110+/Nt
Save with Expedia, $19/night less
PRICEDESTINATIONDEAL
$118 New York City, New York Cheap Flights from Washington, DC
DealBase.com
$94 New York City, New York Sun Country Airlines December to Remember Sale
DealBase.com
$207 New York City, New York Cheap Flights from Detroit
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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