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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$445 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $445
Expedia
$218 Chicago, Illinois American Airlines US Flight Deals for Fall
DealBase.com
$692 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $692
Expedia
$332 Chicago, Illinois American Airlines US Flight Deals for Fall
DealBase.com
$126 Chicago, Illinois ACME Company Chicago in Mar: $126 & Up
Save with Expedia, $22/night less
$186 Chicago, Illinois American Airlines US Flight Deals for Fall
DealBase.com
$119 Chicago, Illinois Book 3 Nts in Chicago this Mar Fr $119+/Nt
Expedia
$182 Chicago, Illinois American Airlines US Flight Deals for Fall
DealBase.com
$146 Chicago, Illinois Book 3 Nts in Chicago this Mar Fr $146+/Nt
Expedia
$244 Chicago, Illinois American Airlines US Spring Flight Deals
DealBase.com
$189 Chicago, Illinois Book 3 Nts in Chicago this Mar Fr $189+/Nt
Expedia
$276 Chicago, Illinois American Airlines US Spring Flight Deals
DealBase.com
$320 Chicago, Illinois Book 3-Star Holiday Inn Chicago - Midway Airport Fr $320+/Nt
Expedia
$178 Chicago, Illinois American Airlines US Spring Flight Deals
DealBase.com
$136 Chicago, Illinois Book 3.5-Star Central Loop Fr $136+/Nt
Expedia
$230 Chicago, Illinois American Airlines US Spring Flight Deals
DealBase.com
$159 Chicago, Illinois Book 3.5-Star Hilton Suites Chicago/Magnificent Mile Fr $159+/Nt
Expedia
$184 Chicago, Illinois American Airlines US Spring Flight Deals
DealBase.com
$117 Chicago, Illinois Book 3.5-Star Kinzie in Chicago Fr $117+/Nt
Save with Expedia, $29/night less
$300 Chicago, Illinois American Airlines US Spring Flight Deals
DealBase.com
$141 Chicago, Illinois Book 3.5-Star Wyndham Grand Chicago Riverfront Fr $141+/Nt
Save with Expedia, $25/night less
$9 Chicago, Illinois Cheap Car Rentals in Chicago Fr $9/Day
CarRentals.com
$161 Chicago, Illinois Book 4-Star Burnham - a Kimpton Fr $161+/Nt
Save with Expedia, $28/night less
$89+ Chicago, Illinois Chicago Hotel Deals For As Low As $89/nt!
Jetsetter
$109 Chicago, Illinois Book 4-Star Hilton Chicago O'Hare Airport in Chicago Fr $109+/Nt
Expedia
$103 Chicago, Illinois Delta US Fare Sale
DealBase.com
$147 Chicago, Illinois Book 4.5-Star Sofitel Chicago Water Tower Fr $147+/Nt
Expedia
$115 Chicago, Illinois Delta US Fare Sale
DealBase.com
$147 Chicago, Illinois Book 4.5-Star The James Chicago Fr $147+/Nt
Save with Expedia, $49/night less
$38+ Chicago, Illinois Dolands Addition Vacation Rental Deals From $38
Tripping
$250 Chicago, Illinois Book 5-Star Four Seasons Chicago in Chicago Fr $250+/Nt
Save with Expedia, $125/night less
$142+ Chicago, Illinois Experience Chicago! Book Cheap Flights From $142 R/T
Fare Buzz
$109 Chicago, Illinois Book in Chicago: Save at the Congress Plaza in Mar Fr $109+/Nt
Save with Expedia, $27/night less
$166 Chicago, Illinois Southwest Airlines Low Fares on Flights
DealBase.com
$149 Chicago, Illinois Book in Chicago: Save at the The Silversmith in Mar Fr $149+/Nt
Expedia
$190 Chicago, Illinois Southwest Airlines Low Fares on Flights
DealBase.com
$123 Chicago, Illinois Book in Chicago: Save this Mar Fr $123+/Nt
Expedia
$89 Chicago, Illinois Southwest Airlines Low Fares on Flights
DealBase.com
$140 Chicago, Illinois Book in Chicago: Save this Mar Fr $140+/Nt
Expedia
$175 Chicago, Illinois Southwest Airlines Low Fares on Flights
DealBase.com
$169 Chicago, Illinois Book in Chicago: Save this Mar Fr $169+/Nt
Expedia
$128 Chicago, Illinois Southwest Airlines Low Fares on Flights
DealBase.com
$90 Chicago, Illinois Book in Chicago: Save this Mar Fr $90+/Nt
Save with Expedia, $9/night less
$115 Chicago, Illinois Southwest Airlines Low Fares on Flights
DealBase.com
$101 Chicago, Illinois Book the Chicago's Essex Inn 3 Nts in Mar Fr $101+/Nt
Expedia
$172 Chicago, Illinois Southwest Airlines Low Fares on Flights
DealBase.com
$174 Chicago, Illinois Book the Embassy Suites Chicago Downtown 3 Nts in Mar Fr $174+/Nt
Expedia
$137 Chicago, Illinois Southwest Airlines Low Fares on Flights
DealBase.com
$108 Chicago, Illinois Book the Holiday Inn Chicago Downtown 3 Nts in Mar Fr $108+/Nt
Expedia
$171 Chicago, Illinois Southwest Airlines Low Fares on Flights
DealBase.com
$163 Chicago, Illinois Book the JW Marriott Chicago 3 Nts in Mar Fr $163+/Nt
Expedia
$179 Chicago, Illinois Virgin America Great Deals Across the US
DealBase.com
$191 Chicago, Illinois Book the Radisson Blu Aqua 3 Nts in Mar Fr $191+/Nt
Expedia
$200 Chicago, Illinois Virgin America Great Deals Across the US
DealBase.com
$1,123 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $1,123
Expedia
$200 Chicago, Illinois Virgin America Great Deals Across the US
DealBase.com
$116 Chicago, Illinois Chicago Savings! Book 3 Nts in Mar Fr $116+/Nt
Save with Expedia, $21/night less
$179 Chicago, Illinois Virgin America Great Deals Across the US
DealBase.com
$159 Chicago, Illinois Chicago Savings! Book 3 Nts in Mar Fr $159+/Nt
Expedia
$200 Chicago, Illinois Virgin America Great Deals Across the US
DealBase.com
$217 Chicago, Illinois Chicago Savings! Book 3 Nts in Mar Fr $217+/Nt
Expedia
$200 Chicago, Illinois Virgin America Great Deals Across the US
DealBase.com
$136 Chicago, Illinois Chicago Savings! Book at Allegro Chicago - a Kimpton Fr $136+/Nt
Save with Expedia, $23/night less
$161 Chicago, Illinois Chicago Savings! Book at Monaco Chicago - a Kimpton Fr $161+/Nt
Save with Expedia, $28/night less
$153 Chicago, Illinois Chicago Savings! Book at Palomar Chicago, a Kimpton Fr $153+/Nt
Save with Expedia, $26/night less
$166 Chicago, Illinois Chicago Savings! Book at The Blackstone A Renaissance Fr $166+/Nt
Expedia
$234 Chicago, Illinois Chicago Savings! Book at The Peninsula Chicago Fr $234+/Nt
Save with Expedia, $116/night less
$150 Chicago, Illinois Chicago Savings! Book at W Chicago - City Center Fr $150+/Nt
Expedia
$154 Chicago, Illinois Chicago Savings! Book at W Chicago Lakeshore Fr $154+/Nt
Expedia
$114 Chicago, Illinois Crowne Plaza Chicago - The Metro in Mar: $114 & Up
Expedia
$153 Chicago, Illinois dana and spa in Mar: $153 & Up
Expedia
$105 Chicago, Illinois Doubletree by Hilton Chicago Magnificent Mile in Mar: $105 & Up
Expedia
$153 Chicago, Illinois Hampton Inn & Suites Chicago - Downtown in Mar: $153 & Up
Expedia
$113 Chicago, Illinois Mar deal: Club Quarters Chicago - Central Loop Fr $113+/Nt
Expedia
$144 Chicago, Illinois Mar deal: Fairmont Chicago Millennium Park Fr $144+/Nt
Save with Expedia, $16/night less
$169 Chicago, Illinois Mar deal: Hampton Majestic Chicago Theatre District Fr $169+/Nt
Expedia
$164 Chicago, Illinois Mar deal: Hard Rock Chicago Fr $164+/Nt
Save with Expedia, $29/night less
$126 Chicago, Illinois Mar deal: Hilton Chicago Fr $126+/Nt
Expedia
$109 Chicago, Illinois Mar deal: Hostelling International Chicago Fr $109+/Nt
Expedia
$112 Chicago, Illinois Mar deal: Indigo Chicago Downtown Gold Coast Fr $112+/Nt
Expedia
$259 Chicago, Illinois Mar deal: Park Hyatt Chicago Fr $259+/Nt
Expedia
$219 Chicago, Illinois Mar deal: Renaissance Chicago Fr $219+/Nt
Expedia
$88 Chicago, Illinois Mar deal: Travelodge Chicago Downtown Fr $88+/Nt
Expedia
$130 Chicago, Illinois MileNorth, A Chicago on Sale: Book 3 Nts in Mar Fr $130+/Nt
Save with Expedia, $43/night less
$253 Chicago, Illinois Renaissance Chicago O'Hare Suites in Mar: $253 & Up
Expedia
$111 Chicago, Illinois Save at 3-Star BEST WESTERN River North: $111 & Up in Mar
Expedia
$1,127 Chicago, Illinois Save at 3.5-Star Hotel: 3 Nts + Air to Chicago Fr $1,127
Expedia
$1,520 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $1,520
Expedia
$1,898 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $1,898
Expedia
$486 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $486
Expedia
$112 Chicago, Illinois Save at 4-Star Hyatt Regency Chicago: $112 & Up in Mar
Expedia
$163 Chicago, Illinois Save at 4-Star Swissotel Chicago: $163 & Up in Mar
Save with Expedia, $41/night less
$1,119 Chicago, Illinois Save at 4.5-Star Hotel: 3 Nts + Air to Chicago Fr $1,119
Expedia
$128 Chicago, Illinois Save at 4.5-Star InterContinental Chicago: $128 & Up in Mar
Expedia
$162 Chicago, Illinois Save Big This Mar! Book 3 Nts at Days Inn Chicago Fr $162+/Nt
Expedia
$119 Chicago, Illinois Save Big This Mar! Book 3 Nts at The Whitehall Fr $119+/Nt
Save with Expedia, $20/night less
$139 Chicago, Illinois Save Big This Mar! Book 3 Nts in Chicago Fr $139+/Nt
Expedia
$143 Chicago, Illinois Save Big This Mar! Book 3 Nts in Chicago Fr $143+/Nt
Expedia
$100 Chicago, Illinois Save in Chicago: Book 3 Nts in Mar Fr $100+/Nt
Expedia
$129 Chicago, Illinois Save in Chicago: Book 3 Nts in Mar Fr $129+/Nt
Expedia
PRICEDESTINATIONDEAL
$114 Newark, New Jersey Cheap Flights from Boston
DealBase.com
$225 Newark, New Jersey Cheap Flights from Ft. Lauderdale
DealBase.com
$280 Newark, New Jersey Cheap Flights from Seattle
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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