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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 Cheap Car Rentals in Chicago Fr $100/Day
CarRentals.com
$74 Chicago, Illinois Frontier Airlines Evergreen Sale
DealBase.com
$103 Chicago, Illinois Cheap Car Rentals in Chicago Fr $103/Day
CarRentals.com
SAVE Chicago, Illinois SAVEHyatt Regency Chicago
Priceline.com
$104 Chicago, Illinois Cheap Car Rentals in Chicago Fr $104/Day
CarRentals.com
$136 Chicago, Illinois Southwest Airlines Low Fares for Fall Travel
DealBase.com
$105 Chicago, Illinois Cheap Car Rentals in Chicago Fr $105/Day
CarRentals.com
$153 Chicago, Illinois Southwest Airlines Low Fares for Fall Travel
DealBase.com
$110 Chicago, Illinois Cheap Car Rentals in Chicago Fr $110/Day
CarRentals.com
$99 Chicago, Illinois Southwest Airlines Low Fares for Fall Travel
DealBase.com
$114 Chicago, Illinois Cheap Car Rentals in Chicago Fr $114/Day
CarRentals.com
$179 Chicago, Illinois Southwest Airlines Low Fares for Fall Travel
DealBase.com
$123 Chicago, Illinois Cheap Car Rentals in Chicago Fr $123/Day
CarRentals.com
$110 Chicago, Illinois Southwest Airlines Low Fares for Fall Travel
DealBase.com
$125 Chicago, Illinois Cheap Car Rentals in Chicago Fr $125/Day
CarRentals.com
$170 Chicago, Illinois Southwest Airlines Low Fares for Fall Travel
DealBase.com
$149 Chicago, Illinois Cheap Car Rentals in Chicago Fr $149/Day
CarRentals.com
$161 Chicago, Illinois Southwest Airlines Low Fares for Fall Travel
DealBase.com
$154 Chicago, Illinois Cheap Car Rentals in Chicago Fr $154/Day
CarRentals.com
$101 Chicago, Illinois Southwest Airlines Low Fares for Fall Travel
DealBase.com
$155 Chicago, Illinois Cheap Car Rentals in Chicago Fr $155/Day
CarRentals.com
$144 Chicago, Illinois Southwest Airlines Low Fares for Fall Travel
DealBase.com
$159 Chicago, Illinois Cheap Car Rentals in Chicago Fr $159/Day
CarRentals.com
$89 Chicago, Illinois Southwest Airlines Low Fares for Fall Travel
DealBase.com
$160 Chicago, Illinois Cheap Car Rentals in Chicago Fr $160/Day
CarRentals.com
$183 Chicago, Illinois Southwest Airlines Low Fares for Fall Travel
DealBase.com
$166 Chicago, Illinois Cheap Car Rentals in Chicago Fr $166/Day
CarRentals.com
$126 Chicago, Illinois Southwest Airlines Low Fares for Fall Travel
DealBase.com
$179 Chicago, Illinois Cheap Car Rentals in Chicago Fr $179/Day
CarRentals.com
$186 Chicago, Illinois Southwest Airlines Low Fares for Fall Travel
DealBase.com
$200 Chicago, Illinois Cheap Car Rentals in Chicago Fr $200/Day
CarRentals.com
$124 Chicago, Illinois Southwest Airlines Low Fares for Fall Travel
DealBase.com
$210 Chicago, Illinois Cheap Car Rentals in Chicago Fr $210/Day
CarRentals.com
$154 Chicago, Illinois Southwest Airlines Phoenix Sale
DealBase.com
$249 Chicago, Illinois Cheap Car Rentals in Chicago Fr $249/Day
CarRentals.com
$144 Chicago, Illinois United Airlines US Fare Sale for Fall Travel
DealBase.com
$29 Chicago, Illinois Cheap Car Rentals in Chicago Fr $29/Day
CarRentals.com
$278 Chicago, Illinois United Airlines Weekend Specials for 5/27/16
DealBase.com
$30 Chicago, Illinois Cheap Car Rentals in Chicago Fr $30/Day
CarRentals.com
$278 Chicago, Illinois United Airlines Weekend Specials for 5/27/16
DealBase.com
$31 Chicago, Illinois Cheap Car Rentals in Chicago Fr $31/Day
CarRentals.com
$149 Chicago, Illinois Virgin America Land the Lowest Fares
DealBase.com
$32 Chicago, Illinois Cheap Car Rentals in Chicago Fr $32/Day
CarRentals.com
$179 Chicago, Illinois Virgin America Land the Lowest Fares
DealBase.com
$33 Chicago, Illinois Cheap Car Rentals in Chicago Fr $33/Day
CarRentals.com
$38 Chicago, Illinois Cheap Car Rentals in Chicago Fr $38/Day
CarRentals.com
$39 Chicago, Illinois Cheap Car Rentals in Chicago Fr $39/Day
CarRentals.com
$40 Chicago, Illinois Cheap Car Rentals in Chicago Fr $40/Day
CarRentals.com
$41 Chicago, Illinois Cheap Car Rentals in Chicago Fr $41/Day
CarRentals.com
$42 Chicago, Illinois Cheap Car Rentals in Chicago Fr $42/Day
CarRentals.com
$43 Chicago, Illinois Cheap Car Rentals in Chicago Fr $43/Day
CarRentals.com
$44 Chicago, Illinois Cheap Car Rentals in Chicago Fr $44/Day
CarRentals.com
$47 Chicago, Illinois Cheap Car Rentals in Chicago Fr $47/Day
CarRentals.com
$51 Chicago, Illinois Cheap Car Rentals in Chicago Fr $51/Day
CarRentals.com
$516 Chicago, Illinois Cheap Car Rentals in Chicago Fr $516/Day
CarRentals.com
$52 Chicago, Illinois Cheap Car Rentals in Chicago Fr $52/Day
CarRentals.com
$69 Chicago, Illinois Cheap Car Rentals in Chicago Fr $69/Day
CarRentals.com
$70 Chicago, Illinois Cheap Car Rentals in Chicago Fr $70/Day
CarRentals.com
$71 Chicago, Illinois Cheap Car Rentals in Chicago Fr $71/Day
CarRentals.com
$72 Chicago, Illinois Cheap Car Rentals in Chicago Fr $72/Day
CarRentals.com
$73 Chicago, Illinois Cheap Car Rentals in Chicago Fr $73/Day
CarRentals.com
$75 Chicago, Illinois Cheap Car Rentals in Chicago Fr $75/Day
CarRentals.com
$77 Chicago, Illinois Cheap Car Rentals in Chicago Fr $77/Day
CarRentals.com
$78 Chicago, Illinois Cheap Car Rentals in Chicago Fr $78/Day
CarRentals.com
$80 Chicago, Illinois Cheap Car Rentals in Chicago Fr $80/Day
CarRentals.com
$82 Chicago, Illinois Cheap Car Rentals in Chicago Fr $82/Day
CarRentals.com
$83 Chicago, Illinois Cheap Car Rentals in Chicago Fr $83/Day
CarRentals.com
$90 Chicago, Illinois Cheap Car Rentals in Chicago Fr $90/Day
CarRentals.com
$91 Chicago, Illinois Cheap Car Rentals in Chicago Fr $91/Day
CarRentals.com
$93 Chicago, Illinois Cheap Car Rentals in Chicago Fr $93/Day
CarRentals.com
$94 Chicago, Illinois Cheap Car Rentals in Chicago Fr $94/Day
CarRentals.com
$98 Chicago, Illinois Cheap Car Rentals in Chicago Fr $98/Day
CarRentals.com
$99 Chicago, Illinois Cheap Car Rentals in Chicago Fr $99/Day
CarRentals.com
PRICEDESTINATIONDEAL
$294 Philadelphia, Pennsylvania Cheap Flights from Los Angeles
DealBase.com
$158 Philadelphia, Pennsylvania United Airlines US Fare Sale for Fall Travel
DealBase.com
$145 Philadelphia, Pennsylvania Cheap Flights from Boston
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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