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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$228 Chicago, Illinois United Airlines Weekend Specials for 8/10/15
DealBase.com
$200 Chicago, Illinois Virgin America Low Fares
DealBase.com
$136 Chicago, Illinois Central Loop in Aug: $136 & Up
Expedia
$89 Chicago, Illinois Southwest Airlines Nationwide Sale
DealBase.com
$183 Chicago, Illinois Chicago Savings! Book 3 Nts in Aug at The Whitehall Fr $183+/Nt
Save with Expedia, $20/night less
$94 Chicago, Illinois Southwest Airlines Nationwide Sale
DealBase.com
$186 Chicago, Illinois W Chicago - City Center in Aug: $186 & Up
Expedia
$170 Chicago, Illinois Southwest Airlines Nationwide Sale
DealBase.com
$175 Chicago, Illinois Book 3 Nts in Chicago this Aug Fr $175+/Nt
Save with Expedia, $31/night less
$100 Chicago, Illinois Southwest Airlines Nationwide Sale
DealBase.com
$97 Chicago, Illinois Chicago Savings! Book at Travelodge Chicago Downtown Fr $97+/Nt
Expedia
$112 Chicago, Illinois Southwest Airlines Nationwide Sale
DealBase.com
$186 Chicago, Illinois Save in Chicago: Book 3 Nts in Aug Fr $186+/Nt
Expedia
$69 Chicago, Illinois Frontier Airlines Fall Travel Specials
DealBase.com
$364 Chicago, Illinois Small budget: Stay in Chicago this Aug Fr $364+/Nt
Save with Expedia, $181/night less
$171 Chicago, Illinois Southwest Airlines Nationwide Sale
DealBase.com
$189 Chicago, Illinois Chicago Downtown, Autograph Collection in Aug: $189 & Up
Expedia
$200 Chicago, Illinois Virgin America Low Fares
DealBase.com
$153 Chicago, Illinois Small budget: Stay in Chicago this Aug Fr $153+/Nt
Expedia
$147 Chicago, Illinois Southwest Airlines Nationwide Sale
DealBase.com
$149 Chicago, Illinois Chicago Savings! Book at Club Quarters, Central Loop Fr $149+/Nt
Expedia
$126 Chicago, Illinois Southwest Airlines Nationwide Sale
DealBase.com
$200 Chicago, Illinois Book the theWit - A DoubleTree by Hilton 3 Nts in Aug Fr $200+/Nt
Expedia
$180 Chicago, Illinois Southwest Airlines Nationwide Sale
DealBase.com
$190 Chicago, Illinois Book the Hyatt Chicago Magnificent Mile 3 Nts in Aug Fr $190+/Nt
Expedia
$189 Chicago, Illinois Virgin America Low Fares
DealBase.com
$129 Chicago, Illinois Book 4-Star The Palmer House Hilton in Chicago Fr $129+/Nt
Expedia
$320 Chicago, Illinois American Airlines Domestic Getaways for Next Weekend - 8/14/15
DealBase.com
$349 Chicago, Illinois Save Big This Aug! Book 3 Nts in Chicago Fr $349+/Nt
Expedia
$147 Chicago, Illinois Southwest Airlines Nationwide Sale
DealBase.com
$149 Chicago, Illinois Save in Chicago: Book 3 Nts in Aug at Hilton Chicago Fr $149+/Nt
Expedia
$200 Chicago, Illinois Virgin America Low Fares
DealBase.com
$174 Chicago, Illinois Hilton Suites Chicago/Magnificent Mile in Aug: $174 & Up
Expedia
$69 Chicago, Illinois Frontier Airlines Fall Travel Specials
DealBase.com
$332 Chicago, Illinois Chicago Savings! Book at Waldorf Astoria Chicago Fr $332+/Nt
Expedia
$116 Chicago, Illinois Southwest Airlines Nationwide Sale
DealBase.com
$179 Chicago, Illinois Allegro Chicago - a Kimpton in Aug: $179 & Up
Expedia
$200 Chicago, Illinois Virgin America Low Fares
DealBase.com
$141 Chicago, Illinois Save at 4-Star dana and spa: $141 & Up in Aug
Save with Expedia, $35/night less
$139 Chicago, Illinois Virgin America Low Fares
DealBase.com
$156 Chicago, Illinois Book 4-Star Felix in Chicago Fr $156+/Nt
Save with Expedia, $28/night less
$105+ Chicago, Illinois $105: The Palmer House Hilton, Chicago
Priceline.com
$136 Chicago, Illinois Small budget: Stay in Chicago this Aug Fr $136+/Nt
Expedia
$139+ Chicago, Illinois $139: The Drake Hotel, Chicago
Priceline.com
$195 Chicago, Illinois Book the Sheraton Chicago and Towers 3 Nts in Aug Fr $195+/Nt
Expedia
$141+ Chicago, Illinois $141: Hard Rock Hotel Chicago
Priceline.com
$199 Chicago, Illinois The Drake in Aug: $199 & Up
Expedia
$181+ Chicago, Illinois $181: Hotel Burnham, a Kimpton Hotel, Chicago
Priceline.com
$192 Chicago, Illinois Book in Chicago: Save this Aug Fr $192+/Nt
Save with Expedia, $21/night less
$153+ Chicago, Illinois $153: Chicago Marriott Midway
Priceline.com
$110 Chicago, Illinois Chicago's Essex Inn in Aug: $110 & Up
Save with Expedia, $19/night less
$135+ Chicago, Illinois $135: The Westin Chicago River North
Priceline.com
$179 Chicago, Illinois Save in Chicago: Book 3 Nts in Aug Fr $179+/Nt
Expedia
$134+ Chicago, Illinois $134: Congress Plaza Hotel, Chicago
Priceline.com
$161 Chicago, Illinois Aug deal: Raffaello Fr $161+/Nt
Save with Expedia, $28/night less
$138+ Chicago, Illinois $138: dana hotel and spa, Chicago
Priceline.com
$113 Chicago, Illinois Special deal: 3-Star Chicago South Loop Fr $113+/Nt
Save with Expedia, $20/night less
$88+ Chicago, Illinois $88: Embassy Suites Chicago Downtown
Priceline.com
$148 Chicago, Illinois Special deal: 4-Star Warwick Allerton Chicago Fr $148+/Nt
Expedia
$100+ Chicago, Illinois $100: Chicago Lake Shore Hotel
Priceline.com
$174 Chicago, Illinois Chicago Savings! Book 3 Nts in Aug Fr $174+/Nt
Expedia
$188+ Chicago, Illinois $188: Loews Chicago Hotel
Priceline.com
$181 Chicago, Illinois Save Big This Aug! Book 3 Nts in Chicago at Kinzie Fr $181+/Nt
Save with Expedia, $32/night less
$145+ Chicago, Illinois $145: PUBLIC Chicago
Priceline.com
$144 Chicago, Illinois Chicago Savings! Book 3 Nts in Aug Fr $144+/Nt
Expedia
$395+ Chicago, Illinois $395: The Peninsula Chicago
Priceline.com
$152 Chicago, Illinois Save in Chicago: Book 3 Nts in Aug Fr $152+/Nt
Expedia
$242+ Chicago, Illinois $242: Four Seasons Hotel Chicago
Priceline.com
$149 Chicago, Illinois Hyatt Regency McCormick Place in Aug: $149 & Up
Expedia
$152+ Chicago, Illinois $152: Hotel Monaco Chicago, a Kimpton Hotel
Priceline.com
$161 Chicago, Illinois Aug deal: Crowne Plaza Chicago - The Metro Fr $161+/Nt
Expedia
$89+ Chicago, Illinois Chicago Hotel Deals For As Low As $89/nt!
Jetsetter
$189 Chicago, Illinois Chicago Savings! Book 3 Nts in Aug Fr $189+/Nt
Expedia
$119+ Chicago, Illinois $119: Hyatt Regency Chicago
Priceline.com
$193 Chicago, Illinois Save at 4.5-Star InterContinental Chicago: $193 & Up in Aug
Expedia
$149+ Chicago, Illinois $149: Crowne Plaza Chicago Metro
Hotels.com
$192 Chicago, Illinois Book in Chicago: Save at the Omni Chicago in Aug Fr $192+/Nt
Save with Expedia, $47/night less
$101+ Chicago, Illinois $101: Millennium Knickerbocker, Chicago
Priceline.com
$365 Chicago, Illinois Chicago Savings! Book at Park Hyatt Chicago Fr $365+/Nt
Expedia
$109+ Chicago, Illinois $109: Homewood Suites by Hilton Chicago Downtown
Priceline.com
$237 Chicago, Illinois Chicago Savings! Book at Radisson Blu Aqua Fr $237+/Nt
Expedia
$103+ Chicago, Illinois $103: Chicago South Loop Hotel
Priceline.com
$198 Chicago, Illinois Fairmont Chicago Millennium Park in Aug: $198 & Up
Save with Expedia, $35/night less
$123+ Chicago, Illinois $123: Raffaello Hotel, Chicago
Priceline.com
$204 Chicago, Illinois BEST WESTERN Grant Park in Aug: $204 & Up
Expedia
$89+ Chicago, Illinois $89: City Suites Hotel, Chicago
Priceline.com
$138 Chicago, Illinois $138 & Up: ACME Company Chicago 3-Star Hotel in Chicago
Save with Expedia, $25/night less
$92+ Chicago, Illinois $92: ACME Hotel Company Chicago
Priceline.com
$128 Chicago, Illinois Book 4-Star The Tremont Chicago at Magnificent Mile Fr $128+/Nt
Expedia
$324+ Chicago, Illinois $324: The Langham Chicago
Priceline.com
$343 Chicago, Illinois Book 5-Star Trump International & Tower Chicago Fr $343+/Nt
Save with Expedia, $86/night less
$147+ Chicago, Illinois $147: Hotel Palomar Chicago, a Kimpton Hotel
Priceline.com
$84 Chicago, Illinois Aug deal: Hostelling International Chicago Fr $84+/Nt
Expedia
SAVE Chicago, Illinois Chicago Vacation Rental Deals From $15
Tripping
$171 Chicago, Illinois Aug deal: Hampton Inn & Suites Chicago - Downtown Fr $171+/Nt
Expedia
$243+ Chicago, Illinois $243: The Ritz-Carlton Chicago - A Four Seasons Hotel
Priceline.com
$170 Chicago, Illinois Book 3 Nts in Chicago this Aug Fr $170+/Nt
Expedia
$71+ Chicago, Illinois $71: Inn of Chicago, an Ascend Hotel Collection Member
Priceline.com
$139 Chicago, Illinois Chicago Savings! Book 3 Nts in Aug Fr $139+/Nt
Expedia
$155+ Chicago, Illinois $155: Sofitel Chicago Water Tower
Priceline.com
PRICEDESTINATIONDEAL
$81 Philadelphia, Pennsylvania Cheap Flights from Dallas
DealBase.com
$129 Philadelphia, Pennsylvania Southwest Airlines Nationwide Sale
DealBase.com
$117 Philadelphia, Pennsylvania Cheap Flights from Boston
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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