When To Go
Despite its reputation as the "windy city," Chicago really isn't any more blustery than other northern cities in the continental United States. The average temperature in Chicago bottoms out at 21 degrees in January and hovers around a very muggy 73 degrees in July. That said, with its endless lineup of cultural events and outdoor activities, summer is certainly the best time to visit, though this is also peak tourist season, so you'll be dealing with long lines and crowds and higher prices. Certainly, the city's Stirring Things up in Chicago festival (May 1-October 31; 877-CHICAGO; www.877chicago.com) features an eclectic mix of tours, poetry slams, theater performances, music concerns, cooking classes, unique dining experiences. Come autumn, tourists thin out, students return to school, and the cultural season kicks into high gear, giving the city an electric energy; this is arguably when you'll get your best bang for your buck. That said, if you're traveling on a budget, you'll get the best rates at hotels and cultural attractions in winter – low season. Note that spring is rainy and weather can shift dramatically between warm and cold days.
When To Go
High season:
May to August
Low season:
December to April
Best bang for your buck:
September to November
Under $200+: US fares w/fees & taxes (round-trip) Major Airlines
$59+: Low fares to/from major US cities (one-way) Southwest Airlines
$98+: East Coast city fare sale (round-trip) CheapOair
$49*+: Holiday fares sale to US & Canada (one-way) United/Visa
Holiday packages at Hard Rock Hotels from $99/nt Editors' Review
$239/nt+: Luxury B&B style hotels in top US cities Affinia Hotels
$214/nt+: Luxury Chicago hotel stays w/breakfast Perfect Escapes
$269/nt+: Bed & breakfast rates at Affinia Hotels Affinia Hotels
$290/nt+: Luxury Chicago hotel w/late checkout 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