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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$100+ Chicago, Illinois $100: Chicago Lake Shore Hotel
Priceline.com
$171 Chicago, Illinois $171 & Up: Club Quarters, Central Loop 3.5-Star Hotel in Chicago
Save with Expedia, $18/night less
$101+ Chicago, Illinois $101: Millennium Knickerbocker, Chicago
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$252 Chicago, Illinois $252 & Up: Omni Chicago 4.5-Star Hotel in Chicago
Save with Expedia, $27/night less
$103+ Chicago, Illinois $103: Chicago South Loop Hotel
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$1,029 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $1,029
Expedia
$105+ Chicago, Illinois $105: The Palmer House Hilton, Chicago
Priceline.com
$1,802 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $1,802
Expedia
$109+ Chicago, Illinois $109: Embassy Suites Chicago Downtown - Lakefront
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$919 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $919
Expedia
$111+ Chicago, Illinois $111: Chicago's Essex Inn
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$209 Chicago, Illinois Allegro Chicago - a Kimpton in Jul: $209 & Up
Expedia
$119+ Chicago, Illinois $119: The Palmer House Hilton, Chicago
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$109 Chicago, Illinois Book 3 Nts in Chicago this Jul Fr $109+/Nt
Expedia
$123+ Chicago, Illinois $123: Radisson Blu Aqua Hotel Chicago
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$157 Chicago, Illinois Book 3 Nts in Chicago this Jul Fr $157+/Nt
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$134+ Chicago, Illinois $134: Congress Plaza Hotel, Chicago
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$175 Chicago, Illinois Book 3 Nts in Chicago this Jul Fr $175+/Nt
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$135+ Chicago, Illinois $135: The Westin Chicago River North
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$178 Chicago, Illinois Book 3 Nts in Chicago this Jul Fr $178+/Nt
Save with Expedia, $45/night less
$138+ Chicago, Illinois $138: dana hotel and spa, Chicago
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$179 Chicago, Illinois Book 3 Nts in Chicago this Jul Fr $179+/Nt
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$139+ Chicago, Illinois $139: The Drake Hotel, Chicago
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$216 Chicago, Illinois Book 3 Nts in Chicago this Jul Fr $216+/Nt
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$141+ Chicago, Illinois $141: Hard Rock Hotel Chicago
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$287 Chicago, Illinois Book 3 Nts in Chicago this Jul Fr $287+/Nt
Save with Expedia, $143/night less
$145+ Chicago, Illinois $145: PUBLIC Chicago
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$161 Chicago, Illinois Book 3-Star ACME Company Chicago Fr $161+/Nt
Save with Expedia, $28/night less
$147+ Chicago, Illinois $147: Hotel Palomar Chicago, a Kimpton Hotel
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$156 Chicago, Illinois Book 3-Star Hampton Inn & Suites Chicago - Downtown Fr $156+/Nt
Expedia
$149+ Chicago, Illinois $149: The James Chicago
Hotels.com
$213 Chicago, Illinois Book 3-Star La Quinta Inn & Suites Chicago Downtown Fr $213+/Nt
Expedia
$152+ Chicago, Illinois $152: Hyatt Chicago Magnificent Mile
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$144 Chicago, Illinois Book 3.5-Star Crowne Plaza Chicago - The Metro Fr $144+/Nt
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$153+ Chicago, Illinois $153: Kinzie Hotel, Chicago
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$153 Chicago, Illinois Book 3.5-Star Indigo Chicago Downtown Gold Coast Fr $153+/Nt
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$155+ Chicago, Illinois $155: Sofitel Chicago Water Tower
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$167 Chicago, Illinois Book 4-Star MileNorth, A Chicago Fr $167+/Nt
Expedia
$181+ Chicago, Illinois $181: Hotel Burnham, a Kimpton Hotel, Chicago
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$189 Chicago, Illinois Book 4-Star Sheraton Chicago and Towers in Chicago Fr $189+/Nt
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$188+ Chicago, Illinois $188: Loews Chicago Hotel
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$169 Chicago, Illinois Book 4-Star The Palmer House Hilton in Chicago Fr $169+/Nt
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$242+ Chicago, Illinois $242: Four Seasons Hotel Chicago
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$162 Chicago, Illinois Book 4-Star The Silversmith Fr $162+/Nt
Save with Expedia, $54/night less
$243+ Chicago, Illinois $243: The Ritz-Carlton Chicago - A Four Seasons Hotel
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$169 Chicago, Illinois Book 4-Star The Tremont Chicago at Magnificent Mile Fr $169+/Nt
Expedia
$324+ Chicago, Illinois $324: The Langham Chicago
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$197 Chicago, Illinois Book 4-Star The Westin Michigan Avenue Chicago Fr $197+/Nt
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$395+ Chicago, Illinois $395: The Peninsula Chicago
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$223 Chicago, Illinois Book 4.5-Star The James Chicago in Chicago Fr $223+/Nt
Save with Expedia, $40/night less
$71+ Chicago, Illinois $71: Inn of Chicago, an Ascend Hotel Collection Member
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$183 Chicago, Illinois Book in Chicago: Save at the Central Loop in Jul Fr $183+/Nt
Save with Expedia, $20/night less
$88+ Chicago, Illinois $88: Embassy Suites Chicago Downtown
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$144 Chicago, Illinois Book in Chicago: Save at the Congress Plaza in Jul Fr $144+/Nt
Save with Expedia, $15/night less
$89+ Chicago, Illinois $89: Hampton Inn Chicago Downtown/Magnificent Mile
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$189 Chicago, Illinois Book in Chicago: Save this Jul Fr $189+/Nt
Expedia
$92+ Chicago, Illinois $92: ACME Hotel Company Chicago
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$189 Chicago, Illinois Book in Chicago: Save this Jul Fr $189+/Nt
Expedia
$99+ Chicago, Illinois $99: Hilton Chicago O'Hare Airport
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$212 Chicago, Illinois Book in Chicago: Save this Jul Fr $212+/Nt
Expedia
$9 Chicago, Illinois Cheap Car Rentals in Chicago Fr $9/Day
CarRentals.com
$243 Chicago, Illinois Book in Chicago: Save this Jul Fr $243+/Nt
Expedia
$179+ Chicago, Illinois Chicago 3 -star, Top-rated Hotel - Save 23%! Summer Travel!
Hotelwatchdog
$84 Chicago, Illinois Book the Hostelling International Chicago 3 Nts in Jul Fr $84+/Nt
Expedia
$245+ Chicago, Illinois Chicago 3 -star, Top-rated Hotel - Save 30%! Summer Travel!
Hotelwatchdog
$349 Chicago, Illinois Book the JW Marriott Chicago 3 Nts in Jul Fr $349+/Nt
Expedia
$205+ Chicago, Illinois Chicago 4 -star, Top-rated Hotel - Save 18%! Summer Travel!
Hotelwatchdog
$219 Chicago, Illinois Book the Kinzie 3 Nts in Jul Fr $219+/Nt
Expedia
$207+ Chicago, Illinois Chicago 4 -star, Top-rated Hotel - Save 18%! Summer Travel!
Hotelwatchdog
$225 Chicago, Illinois Book the theWit - A DoubleTree by Hilton 3 Nts in Jul Fr $225+/Nt
Expedia
$189+ Chicago, Illinois Chicago 4 -star, Top-rated Hotel - Save 23%! Summer Travel!
Hotelwatchdog
$1,113 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $1,113
Expedia
$126+ Chicago, Illinois Chicago 4 -star, Top-rated Hotel - Save 29%! Summer Travel!
Hotelwatchdog
$1,365 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $1,365
Expedia
$212+ Chicago, Illinois Chicago 4.5 -star, Top-rated Hotel - Save 14%!
Hotelwatchdog
$1,402 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $1,402
Expedia
$251+ Chicago, Illinois Chicago 4.5 -star, Top-rated Hotel - Save 26%!
Hotelwatchdog
$620 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $620
Expedia
$89+ Chicago, Illinois Chicago Hotel Deals For As Low As $89/nt!
Jetsetter
$988 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $988
Expedia
$49 Chicago, Illinois Frontier Airlines Fall Travel Deals
DealBase.com
$732 Chicago, Illinois Chicago 5-Star Hotel Sale! 3 Nts + Air Fr $732
Expedia
$49 Chicago, Illinois Frontier Airlines Fall Travel Deals
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$162 Chicago, Illinois Chicago Savings! Book 3 Nts in Jul Fr $162+/Nt
Expedia
$49 Chicago, Illinois Frontier Airlines Fall Travel Deals
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$166 Chicago, Illinois Chicago Savings! Book 3 Nts in Jul Fr $166+/Nt
Expedia
$200 Chicago, Illinois Virgin America Low Fares
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$243 Chicago, Illinois Chicago Savings! Book 3 Nts in Jul Fr $243+/Nt
Save with Expedia, $43/night less
$197 Chicago, Illinois Virgin America Low Fares
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$189 Chicago, Illinois Chicago Savings! Book at AC Chicago Downtown Fr $189+/Nt
Expedia
$200 Chicago, Illinois Virgin America Low Fares
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$145 Chicago, Illinois Chicago Savings! Book at BEST WESTERN River North Fr $145+/Nt
Expedia
$200 Chicago, Illinois Virgin America Low Fares
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$199 Chicago, Illinois Chicago Savings! Book at Burnham - a Kimpton Fr $199+/Nt
Expedia
$200 Chicago, Illinois Virgin America Low Fares
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$149 Chicago, Illinois Chicago Savings! Book at Holiday Inn Express Cass Fr $149+/Nt
Expedia
$188 Chicago, Illinois Virgin America Low Fares
DealBase.com
$199 Chicago, Illinois Chicago Savings! Book at Hyatt Regency Chicago Fr $199+/Nt
Expedia
$279 Chicago, Illinois Chicago Savings! Book at Palomar Chicago, a Kimpton Fr $279+/Nt
Expedia
$189 Chicago, Illinois Chicago Savings! Book at Raffaello Fr $189+/Nt
Save with Expedia, $34/night less
PRICEDESTINATIONDEAL
$123 Philadelphia, Pennsylvania Cheap Flights from Orlando
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$49 Philadelphia, Pennsylvania Frontier Airlines Fall Travel Deals
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$143 Philadelphia, Pennsylvania Cheap Flights from Boston
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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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