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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 5/29/15
DealBase.com
$84 Chicago, Illinois Book the Hostelling International Chicago 3 Nts in May Fr $84+/Nt
Expedia
$59 Chicago, Illinois Frontier Airlines School's Out Deals
DealBase.com
$183 Chicago, Illinois Chicago Savings! Book at Kinzie Fr $183+/Nt
Expedia
$180 Chicago, Illinois Virgin America Low Fares
DealBase.com
$314 Chicago, Illinois May deal: Chicago Marriott at Medical District/UIC Fr $314+/Nt
Expedia
$200 Chicago, Illinois Virgin America Low Fares
DealBase.com
$226 Chicago, Illinois Save Big This May! Book 3 Nts in Chicago Fr $226+/Nt
Save with Expedia, $40/night less
$200 Chicago, Illinois Virgin America Low Fares
DealBase.com
$254 Chicago, Illinois Chicago Savings! Book at Sofitel Chicago Water Tower Fr $254+/Nt
Expedia
$200 Chicago, Illinois Virgin America Low Fares
DealBase.com
$236 Chicago, Illinois Book 3 Nts in Chicago this May Fr $236+/Nt
Expedia
$260 Chicago, Illinois American Airlines Domestic Getaways for This Weekend - 5/29/15
DealBase.com
$195 Chicago, Illinois Book 4-Star Chicago Downtown, Autograph Collection Fr $195+/Nt
Expedia
$320 Chicago, Illinois American Airlines Domestic Getaways for This Weekend - 5/29/15
DealBase.com
$195 Chicago, Illinois Save at 4-Star Sheraton Chicago and Towers: $195 & Up in May
Expedia
$330 Chicago, Illinois American Airlines Domestic Getaways for This Weekend - 5/29/15
DealBase.com
$225 Chicago, Illinois Save in Chicago: Book 3 Nts in May at The Silversmith Fr $225+/Nt
Save with Expedia, $24/night less
$268 Chicago, Illinois American Airlines Domestic Getaways for This Weekend - 5/29/15
DealBase.com
$98 Chicago, Illinois Save in Chicago: Book 3 Nts in May Fr $98+/Nt
Save with Expedia, $32/night less
$278 Chicago, Illinois United Airlines Weekend Specials for 5/29/15
DealBase.com
$205 Chicago, Illinois May deal: Warwick Allerton Chicago Fr $205+/Nt
Expedia
$220 Chicago, Illinois American Airlines Domestic Getaways for Next Weekend - 6/5/15
DealBase.com
$190 Chicago, Illinois Chicago Savings! Book 3 Nts in May Fr $190+/Nt
Expedia
$270 Chicago, Illinois American Airlines Domestic Getaways for This Weekend - 5/29/15
DealBase.com
$211 Chicago, Illinois Doubletree by Hilton Chicago Magnificent Mile in May: $211 & Up
Expedia
$330 Chicago, Illinois American Airlines Domestic Getaways for Next Weekend - 6/5/15
DealBase.com
$237 Chicago, Illinois Save in Chicago: Book 3 Nts in May Fr $237+/Nt
Save with Expedia, $26/night less
$310 Chicago, Illinois American Airlines Domestic Getaways for This Weekend - 5/29/15
DealBase.com
$259 Chicago, Illinois Book 3 Nts in Chicago this May Fr $259+/Nt
Expedia
$320 Chicago, Illinois American Airlines Domestic Getaways for This Weekend - 5/29/15
DealBase.com
$189 Chicago, Illinois May deal: Allegro Chicago - a Kimpton Fr $189+/Nt
Expedia
$310 Chicago, Illinois American Airlines Domestic Getaways for This Weekend - 5/29/15
DealBase.com
$215 Chicago, Illinois Chicago Marriott Downtown Magnificent Mile in May: $215 & Up
Expedia
$328 Chicago, Illinois United Airlines Weekend Specials for 5/29/15
DealBase.com
$159 Chicago, Illinois Book 3-Star BEST WESTERN River North in Chicago Fr $159+/Nt
Expedia
$200 Chicago, Illinois Virgin America Low Fares
DealBase.com
$179 Chicago, Illinois Book the The Whitehall 3 Nts in May Fr $179+/Nt
Save with Expedia, $24/night less
$89+ Chicago, Illinois Chicago Hotel Deals For As Low As $89/nt!
Jetsetter
$153 Chicago, Illinois Book in Chicago: Save at the River in May Fr $153+/Nt
Save with Expedia, $16/night less
$149+ Chicago, Illinois $149: The James Chicago
Hotels.com
$214 Chicago, Illinois Chicago Savings! Book at The James Chicago Fr $214+/Nt
Expedia
$129+ Chicago, Illinois $129: Raffaello Hotel, Chicago
Hotels.com
$128 Chicago, Illinois Save in Chicago: Book 3 Nts in May Fr $128+/Nt
Save with Expedia, $31/night less
$395+ Chicago, Illinois $395: The Peninsula Chicago
Priceline.com
$198 Chicago, Illinois Small budget: Stay in Chicago this May Fr $198+/Nt
Save with Expedia, $35/night less
$153+ Chicago, Illinois $153: Kinzie Hotel, Chicago
Priceline.com
$179 Chicago, Illinois Save Big This May! Book 3 Nts in Chicago Fr $179+/Nt
Expedia
$139+ Chicago, Illinois $139: The Drake Hotel, Chicago
Priceline.com
$169 Chicago, Illinois Small budget: Stay in Chicago this May Fr $169+/Nt
Expedia
$188+ Chicago, Illinois $188: Loews Chicago Hotel
Priceline.com
$113 Chicago, Illinois Chicago Savings! Book at Chicago's Essex Inn Fr $113+/Nt
Save with Expedia, $20/night less
$105+ Chicago, Illinois $105: The Palmer House Hilton, Chicago
Priceline.com
$173 Chicago, Illinois Save at 4-Star Hilton Chicago O'Hare Airport: $173 & Up in May
Expedia
$100+ Chicago, Illinois $100: Chicago Lake Shore Hotel
Priceline.com
$140 Chicago, Illinois Book in Chicago: Save this May Fr $140+/Nt
Expedia
$134+ Chicago, Illinois $134: Congress Plaza Hotel, Chicago
Priceline.com
$190 Chicago, Illinois Book 3 Nts in Chicago this May Fr $190+/Nt
Expedia
$123+ Chicago, Illinois $123: Radisson Blu Aqua Hotel Chicago
Priceline.com
$237 Chicago, Illinois Save at 3.5-Star Renaissance Chicago: $237 & Up in May
Expedia
$152+ Chicago, Illinois $152: Hyatt Chicago Magnificent Mile
Priceline.com
$229 Chicago, Illinois Hampton Majestic Chicago Theatre District in May: $229 & Up
Expedia
$103+ Chicago, Illinois $103: The Buckingham Athletic Club & Hotel, Chicago
Priceline.com
$173 Chicago, Illinois Special deal: 4-Star Millennium Knickerbocker Chicago Fr $173+/Nt
Expedia
$145+ Chicago, Illinois $145: PUBLIC Chicago
Priceline.com
$219 Chicago, Illinois Small budget: Book Rush 3 Nts in May Fr $219+/Nt
Expedia
$89+ Chicago, Illinois $89: City Suites Hotel, Chicago
Priceline.com
$204 Chicago, Illinois Book 3.5-Star Crowne Plaza Chicago - The Metro Fr $204+/Nt
Expedia
$159+ Chicago, Illinois $159: Hotel Palomar Chicago, a Kimpton Hotel
Priceline.com
$194 Chicago, Illinois Chicago Savings! Book 3 Nts in May Fr $194+/Nt
Expedia
$138+ Chicago, Illinois $138: dana hotel and spa, Chicago
Priceline.com
$218 Chicago, Illinois Book in Chicago: Save this May Fr $218+/Nt
Expedia
$242+ Chicago, Illinois $242: Four Seasons Hotel Chicago
Priceline.com
$309 Chicago, Illinois May deal: JW Marriott Chicago Fr $309+/Nt
Expedia
$111+ Chicago, Illinois $111: Chicago's Essex Inn
Priceline.com
$181 Chicago, Illinois Book 3.5-Star Blake Chicago Fr $181+/Nt
Expedia
$141+ Chicago, Illinois $141: Hard Rock Hotel Chicago
Priceline.com
$199 Chicago, Illinois $199 & Up: Burnham - a Kimpton 4-Star Hotel in Chicago
Expedia
$181+ Chicago, Illinois $181: Hotel Burnham, a Kimpton Hotel, Chicago
Priceline.com
$177 Chicago, Illinois Monaco Chicago - a Kimpton on Sale: Book 3 Nts in May Fr $177+/Nt
Save with Expedia, $9/night less
$155+ Chicago, Illinois $155: Sofitel Chicago Water Tower
Priceline.com
$187 Chicago, Illinois Book 4-Star MileNorth, A Chicago Fr $187+/Nt
Save with Expedia, $10/night less
$88+ Chicago, Illinois $88: Embassy Suites Chicago Downtown
Priceline.com
$132 Chicago, Illinois Book 3 Nts in Chicago this May Fr $132+/Nt
Save with Expedia, $44/night less
$92+ Chicago, Illinois $92: ACME Hotel Company Chicago
Priceline.com
$156 Chicago, Illinois Book 3 Nts in Chicago this May Fr $156+/Nt
Expedia
$71+ Chicago, Illinois $71: Inn of Chicago, an Ascend Hotel Collection Member
Priceline.com
$229 Chicago, Illinois Save Big This May! Book 3 Nts at The Drake Fr $229+/Nt
Expedia
$243+ Chicago, Illinois $243: The Ritz-Carlton Chicago - A Four Seasons Hotel
Priceline.com
$149 Chicago, Illinois Chicago Savings! Book 3 Nts in May at Congress Plaza Fr $149+/Nt
Expedia
$324+ Chicago, Illinois $324: The Langham Chicago
Priceline.com
$224 Chicago, Illinois Chicago Savings! Book 3 Nts in May at Hilton Chicago Fr $224+/Nt
Expedia
$109+ Chicago, Illinois $109: Hyatt Regency McCormick Place, Chicago
Priceline.com
$238 Chicago, Illinois Save in Chicago: Book 3 Nts in May Fr $238+/Nt
Expedia
$135+ Chicago, Illinois $135: The Westin Chicago River North
Priceline.com
$195 Chicago, Illinois Save at 4-Star The Palmer House Hilton: $195 & Up in May
Expedia
$99+ Chicago, Illinois $99: Hilton Chicago O'Hare Airport
Priceline.com
$189 Chicago, Illinois Book 3-Star Residence Inn Chicago Downtown in Chicago Fr $189+/Nt
Expedia
$101+ Chicago, Illinois $101: Millennium Knickerbocker, Chicago
Priceline.com
$293 Chicago, Illinois Book 4-Star W Chicago - City Center in Chicago Fr $293+/Nt
Expedia
PRICEDESTINATIONDEAL
$49 Philadelphia, Pennsylvania Frontier Airlines School's Out Deals
DealBase.com
$59 Philadelphia, Pennsylvania Frontier Airlines School's Out Deals
DealBase.com
$97 Philadelphia, Pennsylvania Cheap Flights from Atlanta
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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