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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$109 Chicago, Illinois Southwest Airlines Washington DC Deals
DealBase.com
$243 Chicago, Illinois American Airlines Fall Travel Deals
DealBase.com
$235 Chicago, Illinois Chicago Savings! Book 3 Nts in Jun Fr $235+/Nt
Expedia
$134 Chicago, Illinois United Airlines Fall Travel Specials
DealBase.com
$180 Chicago, Illinois Save in Chicago: Book 3 Nts in Jun Fr $180+/Nt
Expedia
$188 Chicago, Illinois Virgin America Low Fares
DealBase.com
$128 Chicago, Illinois Book the BEST WESTERN River North 3 Nts in Jun Fr $128+/Nt
Expedia
$219 Chicago, Illinois American Airlines Fall Travel Deals
DealBase.com
$199 Chicago, Illinois Save Big This Jun! Book 3 Nts in Chicago at The Drake Fr $199+/Nt
Expedia
$162 Chicago, Illinois Southwest Airlines Hit a Grand Slam Sale
DealBase.com
$90 Chicago, Illinois Red Roof Inn Chicago Downtown Magnificent Mile in Jun: $90 & Up
Save with Expedia, $15/night less
$172 Chicago, Illinois Southwest Airlines Hit a Grand Slam Sale
DealBase.com
$183 Chicago, Illinois Courtyard Chicago Downtown River North in Jun: $183 & Up
Expedia
$158 Chicago, Illinois Cheap Flights from Phoenix
DealBase.com
$223 Chicago, Illinois Book in Chicago: Save at the The James Chicago in Jun Fr $223+/Nt
Expedia
$287 Chicago, Illinois American Airlines Fall Travel Deals
DealBase.com
$144 Chicago, Illinois Save Big This Jun! Book 3 Nts in Chicago Fr $144+/Nt
Save with Expedia, $25/night less
$218 Chicago, Illinois Southwest Airlines Mexico and Caribbean Sale
DealBase.com
$203 Chicago, Illinois Book 3-Star Hampton Inn & Suites Chicago - Downtown Fr $203+/Nt
Expedia
$197 Chicago, Illinois Virgin America Low Fares
DealBase.com
$239 Chicago, Illinois Special deal: 4-Star Palomar Chicago, a Kimpton Fr $239+/Nt
Expedia
$49 Chicago, Illinois Frontier Airlines Travel Deals Done Right
DealBase.com
$173 Chicago, Illinois Save at 4-Star Hilton Chicago: $173 & Up in Jun
Expedia
$200 Chicago, Illinois Virgin America Low Fares
DealBase.com
$240 Chicago, Illinois Chicago Savings! Book at W Chicago - City Center Fr $240+/Nt
Expedia
$89 Chicago, Illinois Southwest Airlines Hit a Grand Slam Sale
DealBase.com
$136 Chicago, Illinois Millennium Knickerbocker Chicago in Jun: $136 & Up
Expedia
$309 Chicago, Illinois American Airlines Fall Travel Deals
DealBase.com
$105+ Chicago, Illinois $105: The Palmer House Hilton, Chicago
Priceline.com
$245 Chicago, Illinois American Airlines Fall Travel Deals
DealBase.com
$239 Chicago, Illinois Chicago Savings! Book at AC Chicago Downtown Fr $239+/Nt
Expedia
$116 Chicago, Illinois Southwest Airlines Hit a Grand Slam Sale
DealBase.com
$181 Chicago, Illinois Save Big This Jun! Book 3 Nts in Chicago Fr $181+/Nt
Expedia
$100 Chicago, Illinois Southwest Airlines Hit a Grand Slam Sale
DealBase.com
$216 Chicago, Illinois Save Big This Jun! Book 3 Nts in Chicago Fr $216+/Nt
Expedia
$229 Chicago, Illinois Southwest Airlines Mexico and Caribbean Sale
DealBase.com
$84 Chicago, Illinois Book the Hostelling International Chicago 3 Nts in Jun Fr $84+/Nt
Expedia
$200 Chicago, Illinois Virgin America Low Fares
DealBase.com
$134 Chicago, Illinois Book 3.5-Star Crowne Plaza Chicago - The Metro Fr $134+/Nt
Expedia
$126 Chicago, Illinois Southwest Airlines Hit a Grand Slam Sale
DealBase.com
$195 Chicago, Illinois Save Big This Jun! Book 3 Nts at Hard Rock Chicago Fr $195+/Nt
Save with Expedia, $34/night less
$273 Chicago, Illinois American Airlines Fall Travel Deals
DealBase.com
$260 Chicago, Illinois Chicago Savings! Book at Radisson Blu Aqua Fr $260+/Nt
Expedia
$49 Chicago, Illinois Frontier Airlines Travel Deals Done Right
DealBase.com
$124 Chicago, Illinois Jun deal: Chicago South Loop Fr $124+/Nt
Save with Expedia, $22/night less
$147 Chicago, Illinois Southwest Airlines Hit a Grand Slam Sale
DealBase.com
$243 Chicago, Illinois Chicago Savings! Book 3 Nts in Jun Fr $243+/Nt
Save with Expedia, $27/night less
$200 Chicago, Illinois Virgin America Low Fares
DealBase.com
$155+ Chicago, Illinois $155: Sofitel Chicago Water Tower
Priceline.com
$251 Chicago, Illinois Southwest Airlines Mexico and Caribbean Sale
DealBase.com
$240 Chicago, Illinois Book the The Westin Chicago River North 3 Nts in Jun Fr $240+/Nt
Expedia
$49 Chicago, Illinois Frontier Airlines Travel Deals Done Right
DealBase.com
$208 Chicago, Illinois Jun deal: Omni Chicago Fr $208+/Nt
Save with Expedia, $51/night less
$200 Chicago, Illinois Virgin America Low Fares
DealBase.com
$129 Chicago, Illinois Save Big This Jun! Book 3 Nts in Chicago Fr $129+/Nt
Expedia
$147 Chicago, Illinois Southwest Airlines Hit a Grand Slam Sale
DealBase.com
$83 Chicago, Illinois Small budget: Stay in Chicago this Jun Fr $83+/Nt
Save with Expedia, $56/night less
$112 Chicago, Illinois Southwest Airlines Hit a Grand Slam Sale
DealBase.com
$196 Chicago, Illinois Save Big This Jun! Book 3 Nts in Chicago Fr $196+/Nt
Expedia
$76 Chicago, Illinois Southwest Airlines Hit a Grand Slam Sale
DealBase.com
$117 Chicago, Illinois Save in Chicago: Book 3 Nts in Jun Fr $117+/Nt
Save with Expedia, $39/night less
$363 Chicago, Illinois American Airlines Fall Travel Deals
DealBase.com
$243 Chicago, Illinois Chicago Marriott Downtown Magnificent Mile in Jun: $243 & Up
Expedia
$145 Chicago, Illinois Southwest Airlines Hit a Grand Slam Sale
DealBase.com
$183 Chicago, Illinois Special deal: 4-Star Sheraton Chicago and Towers Fr $183+/Nt
Expedia
$345 Chicago, Illinois American Airlines Fall Travel Deals
DealBase.com
$161 Chicago, Illinois Save Big This Jun! Book 3 Nts in Chicago Fr $161+/Nt
Save with Expedia, $28/night less
$100+ Chicago, Illinois $100: Chicago Lake Shore Hotel
Priceline.com
$204 Chicago, Illinois Save Big This Jun! Book 3 Nts in Chicago Fr $204+/Nt
Save with Expedia, $35/night less
$101+ Chicago, Illinois $101: Millennium Knickerbocker, Chicago
Priceline.com
$166 Chicago, Illinois River in Jun: $166 & Up
Expedia
$134+ Chicago, Illinois $134: Raffaello Hotel, Chicago
Hotels.com
$172 Chicago, Illinois Jun deal: Holiday Inn Chicago Downtown Fr $172+/Nt
Expedia
$92+ Chicago, Illinois $92: ACME Hotel Company Chicago
Priceline.com
$163 Chicago, Illinois Book in Chicago: Save this Jun Fr $163+/Nt
Expedia
$88+ Chicago, Illinois $88: Embassy Suites Chicago Downtown
Priceline.com
$181 Chicago, Illinois Chicago Savings! Book 3 Nts in Jun at Blake Chicago Fr $181+/Nt
Expedia
$135+ Chicago, Illinois $135: The Westin Chicago River North
Priceline.com
$126 Chicago, Illinois Jun deal: The Tremont Chicago at Magnificent Mile Fr $126+/Nt
Expedia
$149+ Chicago, Illinois $149: Crowne Plaza Chicago Metro
Hotels.com
$209 Chicago, Illinois Hampton Majestic Chicago Theatre District in Jun: $209 & Up
Expedia
$123+ Chicago, Illinois $123: Radisson Blu Aqua Hotel Chicago
Priceline.com
$236 Chicago, Illinois Chicago Savings! Book at The Blackstone A Renaissance Fr $236+/Nt
Expedia
$147+ Chicago, Illinois $147: Hotel Palomar Chicago, a Kimpton Hotel
Priceline.com
$330 Chicago, Illinois Book 5-Star Trump International & Tower Chicago Fr $330+/Nt
Save with Expedia, $82/night less
$71+ Chicago, Illinois $71: Inn of Chicago, an Ascend Hotel Collection Member
Priceline.com
$339 Chicago, Illinois JW Marriott Chicago in Jun: $339 & Up
Expedia
$145+ Chicago, Illinois $145: PUBLIC Chicago
Priceline.com
$199 Chicago, Illinois Save at 4.5-Star InterContinental Chicago: $199 & Up in Jun
Expedia
$242+ Chicago, Illinois $242: Four Seasons Hotel Chicago
Priceline.com
$206 Chicago, Illinois Book in Chicago: Save this Jun Fr $206+/Nt
Expedia
$139+ Chicago, Illinois $139: Wyndham Grand Chicago Riverfront
Priceline.com
$193 Chicago, Illinois Book in Chicago: Save this Jun Fr $193+/Nt
Expedia
$188+ Chicago, Illinois $188: Loews Chicago Hotel
Priceline.com
$269 Chicago, Illinois $269 & Up: Renaissance Chicago 4-Star Hotel in Chicago
Expedia
$111+ Chicago, Illinois $111: Chicago's Essex Inn
Priceline.com
$225 Chicago, Illinois Save Big This Jun! Book 3 Nts in Chicago Fr $225+/Nt
Expedia
$119+ Chicago, Illinois $119: Hyatt Regency Chicago
Priceline.com
$199 Chicago, Illinois Small budget: Book Burnham - a Kimpton 3 Nts in Jun Fr $199+/Nt
Expedia
$89+ Chicago, Illinois $89: Hampton Inn Chicago Downtown/Magnificent Mile
Priceline.com
PRICEDESTINATIONDEAL
$225 Philadelphia, Pennsylvania Cheap Flights from Dallas
DealBase.com
$124 Philadelphia, Pennsylvania Cheap Flights from Orlando
DealBase.com
$214 Philadelphia, Pennsylvania Cheap Flights from Las Vegas
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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