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Chicago, IL Hotel Deals

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Chicago, IL Hotel Deals

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TYPE PRICE DESTINATION DEAL
$171 Chicago, Illinois Chicago Savings! Book at BEST WESTERN Grant Park Fr $171+/Nt
Save with Expedia, $19/night less
$395+ Chicago, Illinois $395: The Peninsula Chicago
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$226 Chicago, Illinois May deal: Wyndham Grand Chicago Riverfront Fr $226+/Nt
Save with Expedia, $40/night less
$153+ Chicago, Illinois $153: Kinzie Hotel, Chicago
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$299 Chicago, Illinois Small budget: Stay in Chicago this May Fr $299+/Nt
Expedia
$139+ Chicago, Illinois $139: The Drake Hotel, Chicago
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$236 Chicago, Illinois Save at 4-Star dana and spa: $236 & Up in May
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$105+ Chicago, Illinois $105: The Palmer House Hilton, Chicago
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$171 Chicago, Illinois May deal: Holiday Inn Chicago Downtown Fr $171+/Nt
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$188+ Chicago, Illinois $188: Loews Chicago Hotel
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$178 Chicago, Illinois Book in Chicago: Save this May Fr $178+/Nt
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$100+ Chicago, Illinois $100: Chicago Lake Shore Hotel
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$234 Chicago, Illinois Book 4.5-Star Sofitel Chicago Water Tower Fr $234+/Nt
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$134+ Chicago, Illinois $134: Congress Plaza Hotel, Chicago
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$234 Chicago, Illinois Book 4-Star W Chicago Lakeshore in Chicago Fr $234+/Nt
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$149+ Chicago, Illinois $149: The James Chicago
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$195 Chicago, Illinois Book the Sheraton Chicago and Towers 3 Nts in May Fr $195+/Nt
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$123+ Chicago, Illinois $123: Radisson Blu Aqua Hotel Chicago
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$225 Chicago, Illinois Book in Chicago: Save this May Fr $225+/Nt
Save with Expedia, $24/night less
$152+ Chicago, Illinois $152: Hyatt Chicago Magnificent Mile
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$190 Chicago, Illinois Small budget: Stay in Chicago this May Fr $190+/Nt
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$103+ Chicago, Illinois $103: The Buckingham Athletic Club & Hotel, Chicago
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$211 Chicago, Illinois Chicago Savings! Book 3 Nts in May Fr $211+/Nt
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$145+ Chicago, Illinois $145: PUBLIC Chicago
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$237 Chicago, Illinois Chicago Savings! Book at Swissotel Chicago Fr $237+/Nt
Save with Expedia, $26/night less
$89+ Chicago, Illinois $89: City Suites Hotel, Chicago
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$189 Chicago, Illinois Chicago Savings! Book 3 Nts in May Fr $189+/Nt
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$159+ Chicago, Illinois $159: Hotel Palomar Chicago, a Kimpton Hotel
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$259 Chicago, Illinois Chicago Savings! Book 3 Nts in May at Conrad Chicago Fr $259+/Nt
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$138+ Chicago, Illinois $138: dana hotel and spa, Chicago
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$215 Chicago, Illinois May deal: Chicago Marriott Downtown Magnificent Mile Fr $215+/Nt
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$242+ Chicago, Illinois $242: Four Seasons Hotel Chicago
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$179 Chicago, Illinois Chicago Savings! Book at The Whitehall Fr $179+/Nt
Save with Expedia, $24/night less
$111+ Chicago, Illinois $111: Chicago's Essex Inn
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$159 Chicago, Illinois BEST WESTERN River North on Sale: Book 3 Nts in May Fr $159+/Nt
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$141+ Chicago, Illinois $141: Hard Rock Hotel Chicago
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$153 Chicago, Illinois Save at 3.5-Star River: $153 & Up in May
Save with Expedia, $16/night less
$181+ Chicago, Illinois $181: Hotel Burnham, a Kimpton Hotel, Chicago
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$214 Chicago, Illinois Special deal: 4.5-Star The James Chicago Fr $214+/Nt
Save with Expedia, $115/night less
$155+ Chicago, Illinois $155: Sofitel Chicago Water Tower
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$198 Chicago, Illinois Save at 4-Star Fairmont Chicago Millennium Park: $198 & Up in May
Save with Expedia, $35/night less
$88+ Chicago, Illinois $88: Embassy Suites Chicago Downtown
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$179 Chicago, Illinois Courtyard Chicago Downtown River North in May: $179 & Up
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$92+ Chicago, Illinois $92: ACME Hotel Company Chicago
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$136 Chicago, Illinois Chicago Savings! Book at Central Loop Fr $136+/Nt
Save with Expedia, $33/night less
$243+ Chicago, Illinois $243: The Ritz-Carlton Chicago - A Four Seasons Hotel
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$169 Chicago, Illinois Save in Chicago: Book 3 Nts in May Fr $169+/Nt
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$71+ Chicago, Illinois $71: Inn of Chicago, an Ascend Hotel Collection Member
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$113 Chicago, Illinois May deal: Chicago's Essex Inn Fr $113+/Nt
Save with Expedia, $20/night less
$89+ Chicago, Illinois Chicago Hotel Deals For As Low As $89/nt!
Jetsetter
$173 Chicago, Illinois $173 & Up: Hilton Chicago O'Hare Airport 4-Star Hotel in Chicago
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$324+ Chicago, Illinois $324: The Langham Chicago
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$190 Chicago, Illinois Save in Chicago: Book 3 Nts in May Fr $190+/Nt
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$109+ Chicago, Illinois $109: Hyatt Regency McCormick Place, Chicago
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$223 Chicago, Illinois Book 3 Nts in Chicago this May Fr $223+/Nt
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$135+ Chicago, Illinois $135: The Westin Chicago River North
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$109 Chicago, Illinois Save in Chicago: Book 3 Nts in May Fr $109+/Nt
Save with Expedia, $19/night less
$99+ Chicago, Illinois $99: Hilton Chicago O'Hare Airport
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$237 Chicago, Illinois Chicago Savings! Book at Renaissance Chicago Fr $237+/Nt
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$129+ Chicago, Illinois $129: Raffaello Hotel, Chicago
Hotels.com
$229 Chicago, Illinois Hampton Majestic Chicago Theatre District in May: $229 & Up
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$101+ Chicago, Illinois $101: Millennium Knickerbocker, Chicago
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$219 Chicago, Illinois Small budget: Book Rush 3 Nts in May Fr $219+/Nt
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$119+ Chicago, Illinois $119: Hyatt Regency Chicago
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$204 Chicago, Illinois Crowne Plaza Chicago - The Metro in May: $204 & Up
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$194 Chicago, Illinois Chicago Savings! Book 3 Nts in May Fr $194+/Nt
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$289 Chicago, Illinois Save in Chicago: Book 3 Nts in May Fr $289+/Nt
Expedia
$218 Chicago, Illinois Chicago Savings! Book at The Blackstone A Renaissance Fr $218+/Nt
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$309 Chicago, Illinois Small budget: Stay in Chicago this May Fr $309+/Nt
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$170 Chicago, Illinois Chicago Savings! Book 3 Nts in May at PUBLIC Chicago Fr $170+/Nt
Save with Expedia, $72/night less
$167 Chicago, Illinois Small budget: Book Blake Chicago 3 Nts in May Fr $167+/Nt
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$212 Chicago, Illinois May deal: The Westin Michigan Avenue Chicago Fr $212+/Nt
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$177 Chicago, Illinois Monaco Chicago - a Kimpton in May: $177 & Up
Save with Expedia, $9/night less
$199 Chicago, Illinois Chicago Savings! Book at Burnham - a Kimpton Fr $199+/Nt
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$149 Chicago, Illinois Small budget: Book Congress Plaza 3 Nts in May Fr $149+/Nt
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$177 Chicago, Illinois Chicago Savings! Book at Warwick Allerton Chicago Fr $177+/Nt
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$238 Chicago, Illinois Save at 4-Star theWit - A DoubleTree by Hilton: $238 & Up in May
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$224 Chicago, Illinois Hilton Chicago in May: $224 & Up
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$195 Chicago, Illinois Chicago Savings! Book at The Palmer House Hilton Fr $195+/Nt
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$293 Chicago, Illinois $293 & Up: W Chicago - City Center 4-Star Hotel in Chicago
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$209 Chicago, Illinois Book 4-Star Hyatt Regency McCormick Place Fr $209+/Nt
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$215 Chicago, Illinois May deal: Radisson Blu Aqua Fr $215+/Nt
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$213 Chicago, Illinois Chicago Savings! Book at InterContinental Chicago Fr $213+/Nt
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$240 Chicago, Illinois Chicago Savings! Book 3 Nts in May Fr $240+/Nt
Save with Expedia, $59/night less
$199 Chicago, Illinois Book in Chicago: Save at the The Drake in May Fr $199+/Nt
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$183 Chicago, Illinois Palomar Chicago, a Kimpton in May: $183 & Up
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$212 Chicago, Illinois Chicago Savings! Book 3 Nts in May Fr $212+/Nt
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$229 Chicago, Illinois Book in Chicago: Save this May Fr $229+/Nt
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$198 Chicago, Illinois Small budget: Book Hard Rock Chicago 3 Nts in May Fr $198+/Nt
Save with Expedia, $35/night less
$279 Chicago, Illinois Save at 4-Star MileNorth, A Chicago: $279 & Up in May
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$146 Chicago, Illinois Book 3.5-Star Indigo Chicago Downtown Gold Coast Fr $146+/Nt
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$133 Chicago, Illinois The Tremont Chicago at Magnificent Mile in May: $133 & Up
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$277 Chicago, Illinois Save Big This May! Book 3 Nts in Chicago Fr $277+/Nt
Save with Expedia, $138/night less
$207 Chicago, Illinois Save in Chicago: Book 3 Nts in May Fr $207+/Nt
Expedia
$405 Chicago, Illinois Book 5-Star Four Seasons Chicago Fr $405+/Nt
Expedia
$184 Chicago, Illinois Save at 3-Star Holiday Inn Express Cass: $184 & Up in May
Expedia
$226 Chicago, Illinois Book the Comfort Suites Michigan Avenue 3 Nts in May Fr $226+/Nt
Expedia
$125 Chicago, Illinois Small budget: Stay in Chicago this May Fr $125+/Nt
Save with Expedia, $41/night less
$370 Chicago, Illinois Book 5-Star Trump International & Tower Chicago Fr $370+/Nt
Save with Expedia, $92/night less
$190 Chicago, Illinois Book in Chicago: Save this May Fr $190+/Nt
Expedia
PRICEDESTINATIONDEAL
$138 Philadelphia, Pennsylvania Cheap Flights from Chicago
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$187 Philadelphia, Pennsylvania Cheap Flights from Las Vegas
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$393 Philadelphia, Pennsylvania American Airlines Summer 2015 Deals
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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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