Chicago
Chicago’s nickname, the Windy City, may have been borne of excessive boasting during its bid for the 1893 World Fair – and have nothing whatsoever to do with the weather – but summertime in this Midwestern city definitely warrants bragging rights. In addition to its year-long attractions – think world-class museums, legendary jazz and blues clubs, 7000-plus restaurants, two stellar ball clubs (the Cubs and White Sox) – summer months bring a slew of seasonal events, including The Taste of Chicago summer feast at Grant Park; the critically acclaimed Theater on the Lake; concerts in Highland Park as part of the Ravinia Festival; and the Magnificent Mile Arts Festival, an eclectic display of jewelry, sculpture, photography, and textiles from over 200 local and national artists. You’ll also find 29 magnificent miles of glorious lakefront set below the impressive skyline created by big-name architects like Frank Lloyd Wright and William Le Baron.
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$96+: Round-trip nationwide flights–up to 60% off Major Airlines
$105+: Discount holiday airfares (round-trip) American Airlines
$39-$59 one-way fares to US cities on Southwest Editors' Review
$49+: Winter flights to/from Denver (one-way) Southwest Airlines
$136+: Weekend fares to/from US cities (round-trip) Major Airlines
$145+: US fares (round-trip) within the next 30 days Major Airlines
Under $200+: US fares w/fees & taxes (round-trip) Major Airlines
$98+: East Coast city fare sale (round-trip) CheapOair
$85+: Rock-bottom Thanksgiving fares (one-way) Southwest Airlines
$105+: Last chance at holiday flights (round-trip) NWA
$49*+: Holiday fares sale to US & Canada (one-way) United/Visa
Holiday packages at Hard Rock Hotels from $99/nt Editors' Review
$219/nt+: Chicago luxury boutique hotel w/upgrades The James Hotel
$290/nt+: Luxury Chicago hotel w/late checkout Perfect Escapes
$214/nt+: Luxury Chicago hotel stays w/breakfast Perfect Escapes
$249+: Landmark Chicago hotel w/central location Perfect Escapes
$380+: Quick Chicago 3-nt city escape w/flight Travelocity
$10/nt+: Cheap car rentals from major US airports CarRentals.com