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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$180 Chicago, Illinois Homewood Suites by Hilton Chicago Downtown in Jul: $180 & Up
Expedia
$105+ Chicago, Illinois $105: The Palmer House Hilton, Chicago
Priceline.com
$199 Chicago, Illinois Small budget: Stay in Chicago this Jul Fr $199+/Nt
Expedia
$251+ Chicago, Illinois Chicago 4.5 -star, Top-rated Hotel - Save 26%!
Hotelwatchdog
$166 Chicago, Illinois Jul deal: BEST WESTERN Grant Park Fr $166+/Nt
Expedia
$155+ Chicago, Illinois $155: Sofitel Chicago Water Tower
Priceline.com
$252 Chicago, Illinois Special deal: 4-Star Fairmont Chicago Millennium Park Fr $252+/Nt
Save with Expedia, $44/night less
$188 Chicago, Illinois Virgin America Low Fares
DealBase.com
$225 Chicago, Illinois Chicago Savings! Book at W Chicago - City Center Fr $225+/Nt
Expedia
$49 Chicago, Illinois Frontier Airlines Fall Travel Deals
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$299 Chicago, Illinois Chicago Savings! Book at Renaissance Chicago Fr $299+/Nt
Expedia
$200 Chicago, Illinois Virgin America Low Fares
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$214 Chicago, Illinois Jul deal: Courtyard Chicago Downtown/Magnificent Mile Fr $214+/Nt
Expedia
$197 Chicago, Illinois Virgin America Low Fares
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$223 Chicago, Illinois Chicago Savings! Book at The James Chicago Fr $223+/Nt
Save with Expedia, $40/night less
$100+ Chicago, Illinois $100: Chicago Lake Shore Hotel
Priceline.com
$992 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $992
Expedia
$134+ Chicago, Illinois $134: Raffaello Hotel, Chicago
Hotels.com
$205 Chicago, Illinois Book 4-Star The Westin Michigan Avenue Chicago Fr $205+/Nt
Expedia
$101+ Chicago, Illinois $101: Millennium Knickerbocker, Chicago
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$214 Chicago, Illinois Book the Sofitel Chicago Water Tower 3 Nts in Jul Fr $214+/Nt
Expedia
$92+ Chicago, Illinois $92: ACME Hotel Company Chicago
Priceline.com
$145 Chicago, Illinois Book 3 Nts in Chicago this Jul Fr $145+/Nt
Expedia
$88+ Chicago, Illinois $88: Embassy Suites Chicago Downtown
Priceline.com
$239 Chicago, Illinois Book in Chicago: Save this Jul Fr $239+/Nt
Expedia
$135+ Chicago, Illinois $135: The Westin Chicago River North
Priceline.com
$173 Chicago, Illinois Book 3 Nts in Chicago this Jul Fr $173+/Nt
Expedia
$149+ Chicago, Illinois $149: The James Chicago
Hotels.com
$159 Chicago, Illinois Chicago Savings! Book at Chicago's Essex Inn Fr $159+/Nt
Expedia
$123+ Chicago, Illinois $123: Radisson Blu Aqua Hotel Chicago
Priceline.com
$1,016 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $1,016
Expedia
$147+ Chicago, Illinois $147: Hotel Palomar Chicago, a Kimpton Hotel
Priceline.com
$84 Chicago, Illinois Save Big This Jul! Book 3 Nts in Chicago Fr $84+/Nt
Expedia
$179+ Chicago, Illinois Chicago 3 -star, Top-rated Hotel - Save 23%! Summer Travel!
Hotelwatchdog
$240 Chicago, Illinois Book 3 Nts in Chicago this Jul Fr $240+/Nt
Expedia
$71+ Chicago, Illinois $71: Inn of Chicago, an Ascend Hotel Collection Member
Priceline.com
$209 Chicago, Illinois Chicago Savings! Book at Sheraton Chicago and Towers Fr $209+/Nt
Expedia
$200 Chicago, Illinois Virgin America Low Fares
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$195 Chicago, Illinois Book 4-Star Hard Rock Chicago Fr $195+/Nt
Save with Expedia, $34/night less
$145+ Chicago, Illinois $145: PUBLIC Chicago
Priceline.com
$179 Chicago, Illinois Chicago Savings! Book at AC Chicago Downtown Fr $179+/Nt
Expedia
$242+ Chicago, Illinois $242: Four Seasons Hotel Chicago
Priceline.com
$124 Chicago, Illinois Chicago Savings! Book at Chicago South Loop Fr $124+/Nt
Save with Expedia, $22/night less
$189+ Chicago, Illinois Chicago 4 -star, Top-rated Hotel - Save 23%! Summer Travel!
Hotelwatchdog
$196 Chicago, Illinois Jul deal: La Quinta Inn & Suites Chicago Downtown Fr $196+/Nt
Expedia
$49 Chicago, Illinois Frontier Airlines Fall Travel Deals
DealBase.com
$208 Chicago, Illinois Save Big This Jul! Book 3 Nts at Omni Chicago Fr $208+/Nt
Save with Expedia, $51/night less
$139+ Chicago, Illinois $139: Wyndham Grand Chicago Riverfront
Priceline.com
$224 Chicago, Illinois Book 3 Nts in Chicago this Jul Fr $224+/Nt
Expedia
$188+ Chicago, Illinois $188: Loews Chicago Hotel
Priceline.com
$243 Chicago, Illinois Save Big This Jul! Book 3 Nts in Chicago Fr $243+/Nt
Expedia
$200 Chicago, Illinois Virgin America Low Fares
DealBase.com
$181 Chicago, Illinois Save Big This Jul! Book 3 Nts at The Whitehall Fr $181+/Nt
Save with Expedia, $25/night less
$205+ Chicago, Illinois Chicago 4 -star, Top-rated Hotel - Save 18%! Summer Travel!
Hotelwatchdog
$888 Chicago, Illinois 5-Star Chicago Sale! 3 Nts + Air Fr $888
Expedia
$212+ Chicago, Illinois Chicago 4.5 -star, Top-rated Hotel - Save 14%!
Hotelwatchdog
$756 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $756
Expedia
$245+ Chicago, Illinois Chicago 3 -star, Top-rated Hotel - Save 30%! Summer Travel!
Hotelwatchdog
$218 Chicago, Illinois Special deal: 4-Star Wyndham Grand Chicago Riverfront Fr $218+/Nt
Save with Expedia, $38/night less
$111+ Chicago, Illinois $111: Chicago's Essex Inn
Priceline.com
$830 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $830
Expedia
$49 Chicago, Illinois Frontier Airlines Fall Travel Deals
DealBase.com
$181 Chicago, Illinois Chicago Savings! Book 3 Nts in Jul at Blake Chicago Fr $181+/Nt
Expedia
$200 Chicago, Illinois Virgin America Low Fares
DealBase.com
$145 Chicago, Illinois BEST WESTERN River North in Jul: $145 & Up
Expedia
$181+ Chicago, Illinois $181: Hotel Burnham, a Kimpton Hotel, Chicago
Priceline.com
$892 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $892
Expedia
$99+ Chicago, Illinois $99: Hilton Chicago O'Hare Airport
Priceline.com
$209 Chicago, Illinois Small budget: Stay in Chicago this Jul Fr $209+/Nt
Expedia
$119+ Chicago, Illinois $119: The Palmer House Hilton, Chicago
Priceline.com
$199 Chicago, Illinois Book 3-Star Hampton Inn & Suites Chicago - Downtown Fr $199+/Nt
Expedia
$89+ Chicago, Illinois $89: Hampton Inn Chicago Downtown/Magnificent Mile
Priceline.com
$161 Chicago, Illinois Save in Chicago: Book 3 Nts in Jul Fr $161+/Nt
Save with Expedia, $28/night less
$126+ Chicago, Illinois Chicago 4 -star, Top-rated Hotel - Save 29%! Summer Travel!
Hotelwatchdog
$339 Chicago, Illinois Book 4-Star JW Marriott Chicago Fr $339+/Nt
Expedia
$152+ Chicago, Illinois $152: Hotel Monaco Chicago, a Kimpton Hotel
Priceline.com
$175 Chicago, Illinois Save in Chicago: Book 3 Nts in Jul at River Fr $175+/Nt
Save with Expedia, $28/night less
$324+ Chicago, Illinois $324: The Langham Chicago
Priceline.com
$199 Chicago, Illinois InterContinental Chicago in Jul: $199 & Up
Expedia
$138+ Chicago, Illinois $138: dana hotel and spa, Chicago
Priceline.com
$173 Chicago, Illinois Jul deal: Millennium Knickerbocker Chicago Fr $173+/Nt
Expedia
$109+ Chicago, Illinois $109: Homewood Suites by Hilton Chicago Downtown
Priceline.com
$171 Chicago, Illinois Jul deal: Club Quarters, Central Loop Fr $171+/Nt
Save with Expedia, $18/night less
$89+ Chicago, Illinois Chicago Hotel Deals For As Low As $89/nt!
Jetsetter
$193 Chicago, Illinois Book 3 Nts in Chicago this Jul Fr $193+/Nt
Expedia
$395+ Chicago, Illinois $395: The Peninsula Chicago
Priceline.com
$225 Chicago, Illinois Jul deal: theWit - A DoubleTree by Hilton Fr $225+/Nt
Expedia
$243+ Chicago, Illinois $243: The Ritz-Carlton Chicago - A Four Seasons Hotel
Priceline.com
$345 Chicago, Illinois Chicago Savings! Book 3 Nts in Jul Fr $345+/Nt
Expedia
$103+ Chicago, Illinois $103: Chicago South Loop Hotel
Priceline.com
$289 Chicago, Illinois Conrad Chicago in Jul: $289 & Up
Expedia
$207+ Chicago, Illinois Chicago 4 -star, Top-rated Hotel - Save 18%! Summer Travel!
Hotelwatchdog
$201 Chicago, Illinois Save Big This Jul! Book 3 Nts at W Chicago Lakeshore Fr $201+/Nt
Expedia
$153+ Chicago, Illinois $153: Kinzie Hotel, Chicago
Priceline.com
$130 Chicago, Illinois Save in Chicago: Book 3 Nts in Jul Fr $130+/Nt
Save with Expedia, $86/night less
$141+ Chicago, Illinois $141: Hard Rock Hotel Chicago
Priceline.com
$199 Chicago, Illinois Chicago Savings! Book at Burnham - a Kimpton Fr $199+/Nt
Expedia
$357 Chicago, Illinois Special deal: 5-Star Four Seasons Chicago Fr $357+/Nt
Save with Expedia, $178/night less
$179 Chicago, Illinois Book 4-Star Hyatt Regency McCormick Place Fr $179+/Nt
Expedia
$150 Chicago, Illinois Chicago Savings! Book 3 Nts in Jul Fr $150+/Nt
Expedia
PRICEDESTINATIONDEAL
$99 Philadelphia, Pennsylvania Cheap Flights from Atlanta
DealBase.com
$304 Philadelphia, Pennsylvania Cheap Flights from Los Angeles
DealBase.com
$345 Philadelphia, Pennsylvania Cheap Flights from San Francisco
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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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