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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$155 Chicago, Illinois Embassy Suites by Hilton Chicago Downtown in Aug: $155 & Up
Expedia
$200 Chicago, Illinois Virgin America Low Fares
DealBase.com
$136 Chicago, Illinois Chicago Savings! Book at Central Loop Fr $136+/Nt
Expedia
$105+ Chicago, Illinois $105: The Palmer House Hilton, Chicago
Priceline.com
$149 Chicago, Illinois Book the Hilton Chicago 3 Nts in Aug Fr $149+/Nt
Expedia
$139+ Chicago, Illinois $139: The Drake Hotel, Chicago
Priceline.com
$349 Chicago, Illinois JW Marriott Chicago on Sale: Book 3 Nts in Aug Fr $349+/Nt
Expedia
$94 Chicago, Illinois Southwest Airlines Colorado Day Sale
DealBase.com
$186 Chicago, Illinois Aug deal: W Chicago - City Center Fr $186+/Nt
Expedia
$99 Chicago, Illinois Southwest Airlines Labor Day Weekend Deals
DealBase.com
$174 Chicago, Illinois Chicago Savings! Book 3 Nts in Aug Fr $174+/Nt
Expedia
$141+ Chicago, Illinois $141: Hard Rock Hotel Chicago
Priceline.com
$189 Chicago, Illinois Aug deal: The Whitehall Fr $189+/Nt
Save with Expedia, $20/night less
$181+ Chicago, Illinois $181: Hotel Burnham, a Kimpton Hotel, Chicago
Priceline.com
$175 Chicago, Illinois Special deal: 4-Star Hard Rock Chicago Fr $175+/Nt
Save with Expedia, $31/night less
$153+ Chicago, Illinois $153: Chicago Marriott Midway
Priceline.com
$97 Chicago, Illinois Aug deal: Travelodge Chicago Downtown Fr $97+/Nt
Expedia
$135+ Chicago, Illinois $135: The Westin Chicago River North
Priceline.com
$332 Chicago, Illinois Save Big This Aug! Book 3 Nts in Chicago Fr $332+/Nt
Expedia
$134+ Chicago, Illinois $134: Congress Plaza Hotel, Chicago
Priceline.com
$186 Chicago, Illinois Aug deal: Burnham - a Kimpton Fr $186+/Nt
Expedia
$138+ Chicago, Illinois $138: dana hotel and spa, Chicago
Priceline.com
$364 Chicago, Illinois Four Seasons Chicago on Sale: Book 3 Nts in Aug Fr $364+/Nt
Save with Expedia, $181/night less
$88+ Chicago, Illinois $88: Embassy Suites Chicago Downtown
Priceline.com
$189 Chicago, Illinois Aug deal: Chicago Downtown, Autograph Collection Fr $189+/Nt
Expedia
$100+ Chicago, Illinois $100: Chicago Lake Shore Hotel
Priceline.com
$153 Chicago, Illinois Aug deal: Homewood Suites by Hilton Chicago Downtown Fr $153+/Nt
Expedia
$188+ Chicago, Illinois $188: Loews Chicago Hotel
Priceline.com
$1,004 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $1,004
Expedia
$145+ Chicago, Illinois $145: PUBLIC Chicago
Priceline.com
$1,723 Chicago, Illinois 4.5-Star Chicago Sale! 3 Nts + Air Fr $1,723
Expedia
$9 Chicago, Illinois Cheap Car Rentals in Chicago Fr $9/Day
CarRentals.com
$487 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $487
Expedia
$200 Chicago, Illinois Virgin America Low Fares
DealBase.com
$179 Chicago, Illinois Chicago Savings! Book at Allegro Chicago - a Kimpton Fr $179+/Nt
Expedia
$395+ Chicago, Illinois $395: The Peninsula Chicago
Priceline.com
$200 Chicago, Illinois Aug deal: theWit - A DoubleTree by Hilton Fr $200+/Nt
Expedia
$86 Chicago, Illinois Southwest Airlines Labor Day Weekend Deals
DealBase.com
$190 Chicago, Illinois Hyatt Chicago Magnificent Mile in Aug: $190 & Up
Expedia
$242+ Chicago, Illinois $242: Four Seasons Hotel Chicago
Priceline.com
$129 Chicago, Illinois Chicago Savings! Book at The Palmer House Hilton Fr $129+/Nt
Expedia
$152+ Chicago, Illinois $152: Hotel Monaco Chicago, a Kimpton Hotel
Priceline.com
$141 Chicago, Illinois Chicago Savings! Book at dana and spa Fr $141+/Nt
Save with Expedia, $35/night less
$189 Chicago, Illinois Virgin America Low Fares
DealBase.com
$156 Chicago, Illinois Felix on Sale: Book 3 Nts in Aug Fr $156+/Nt
Save with Expedia, $28/night less
$89+ Chicago, Illinois Chicago Hotel Deals For As Low As $89/nt!
Jetsetter
$136 Chicago, Illinois Book 3-Star Holiday Inn Express Cass in Chicago Fr $136+/Nt
Expedia
$119+ Chicago, Illinois $119: Hyatt Regency Chicago
Priceline.com
$195 Chicago, Illinois Aug deal: Sheraton Chicago and Towers Fr $195+/Nt
Expedia
$149+ Chicago, Illinois $149: Crowne Plaza Chicago Metro
Hotels.com
$2,270 Chicago, Illinois Chicago 5-Star Hotel Sale! 3 Nts + Air Fr $2,270
Expedia
$101+ Chicago, Illinois $101: Millennium Knickerbocker, Chicago
Priceline.com
$199 Chicago, Illinois The Drake in Aug: $199 & Up
Expedia
$109+ Chicago, Illinois $109: MileNorth Hotel, Chicago
Priceline.com
$192 Chicago, Illinois Small budget: Book The Silversmith 3 Nts in Aug Fr $192+/Nt
Save with Expedia, $21/night less
$103+ Chicago, Illinois $103: The Buckingham Athletic Club & Hotel, Chicago
Priceline.com
$110 Chicago, Illinois Save Big This Aug! Book 3 Nts in Chicago Fr $110+/Nt
Save with Expedia, $19/night less
$116 Chicago, Illinois Southwest Airlines Labor Day Weekend Deals
DealBase.com
$179 Chicago, Illinois Book in Chicago: Save this Aug Fr $179+/Nt
Expedia
$123+ Chicago, Illinois $123: Radisson Blu Aqua Hotel Chicago
Priceline.com
$161 Chicago, Illinois Chicago Savings! Book 3 Nts in Aug Fr $161+/Nt
Save with Expedia, $28/night less
$89+ Chicago, Illinois $89: Hampton Inn Chicago Downtown/Magnificent Mile
Priceline.com
$758 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $758
Expedia
$92+ Chicago, Illinois $92: ACME Hotel Company Chicago
Priceline.com
$113 Chicago, Illinois Chicago Savings! Book at Chicago South Loop Fr $113+/Nt
Save with Expedia, $20/night less
$324+ Chicago, Illinois $324: The Langham Chicago
Priceline.com
$148 Chicago, Illinois Aug deal: Warwick Allerton Chicago Fr $148+/Nt
Expedia
$147+ Chicago, Illinois $147: Hotel Palomar Chicago, a Kimpton Hotel
Priceline.com
$174 Chicago, Illinois Courtyard Chicago Downtown/Magnificent Mile in Aug: $174 & Up
Expedia
$200 Chicago, Illinois Virgin America Low Fares
DealBase.com
$181 Chicago, Illinois Kinzie on Sale: Book 3 Nts in Aug Fr $181+/Nt
Save with Expedia, $32/night less
$243+ Chicago, Illinois $243: The Ritz-Carlton Chicago - A Four Seasons Hotel
Priceline.com
$144 Chicago, Illinois Aug deal: Holiday Inn Chicago Mart Plaza River North Fr $144+/Nt
Expedia
$71+ Chicago, Illinois $71: Inn of Chicago, an Ascend Hotel Collection Member
Priceline.com
$152 Chicago, Illinois Save Big This Aug! Book 3 Nts in Chicago Fr $152+/Nt
Expedia
$155+ Chicago, Illinois $155: Sofitel Chicago Water Tower
Priceline.com
$822 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $822
Expedia
$111+ Chicago, Illinois $111: Chicago's Essex Inn
Priceline.com
$161 Chicago, Illinois Save Big This Aug! Book 3 Nts in Chicago Fr $161+/Nt
Expedia
$200 Chicago, Illinois Virgin America Low Fares
DealBase.com
$189 Chicago, Illinois Book 3-Star Comfort Suites Michigan Avenue Fr $189+/Nt
Expedia
$139 Chicago, Illinois Virgin America Low Fares
DealBase.com
$193 Chicago, Illinois Chicago Savings! Book at InterContinental Chicago Fr $193+/Nt
Expedia
$99+ Chicago, Illinois $99: Hilton Chicago O'Hare Airport
Priceline.com
$192 Chicago, Illinois Save at 4.5-Star Omni Chicago: $192 & Up in Aug
Save with Expedia, $47/night less
$365 Chicago, Illinois Save at 5-Star Park Hyatt Chicago: $365 & Up in Aug
Expedia
$237 Chicago, Illinois Book in Chicago: Save at the Radisson Blu Aqua in Aug Fr $237+/Nt
Expedia
$198 Chicago, Illinois Special deal: 4-Star Fairmont Chicago Millennium Park Fr $198+/Nt
Save with Expedia, $35/night less
$204 Chicago, Illinois Chicago Savings! Book at BEST WESTERN Grant Park Fr $204+/Nt
Expedia
$128 Chicago, Illinois Save Big This Aug! Book 3 Nts in Chicago Fr $128+/Nt
Expedia
$343 Chicago, Illinois Aug deal: Trump International & Tower Chicago Fr $343+/Nt
Save with Expedia, $86/night less
$84 Chicago, Illinois Save in Chicago: Book 3 Nts in Aug Fr $84+/Nt
Expedia
$1,113 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $1,113
Expedia
$171 Chicago, Illinois Book 3-Star Hampton Inn & Suites Chicago - Downtown Fr $171+/Nt
Expedia
$170 Chicago, Illinois Save Big This Aug! Book 3 Nts in Chicago Fr $170+/Nt
Expedia
$144 Chicago, Illinois Club Quarters, Central Loop in Aug: $144 & Up
Expedia
$139 Chicago, Illinois Chicago Savings! Book at Holiday Inn Chicago Downtown Fr $139+/Nt
Expedia
$199 Chicago, Illinois Book 3-Star Hampton Majestic Chicago Theatre District Fr $199+/Nt
Expedia
$919 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $919
Expedia
$130 Chicago, Illinois Save in Chicago: Book 3 Nts in Aug Fr $130+/Nt
Expedia
PRICEDESTINATIONDEAL
$81 Philadelphia, Pennsylvania Cheap Flights from Dallas
DealBase.com
$206 Philadelphia, Pennsylvania Cheap Flights from Denver
DealBase.com
$167 Philadelphia, Pennsylvania Cheap Flights from Las Vegas
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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