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
$143/nt+: Chicago hotel w/$50 dining credit & upgrade Perfect Escapes
$209/nt+: Magnificent Mile hotel w/$50 Gift Card InterContinental Chicago Hotel
$229/nt+: Family Chicago stay w/free camera Affinia Chicago
$169+: Affordable rates on stays in DC, NY & more Affinia Hotels
30% off: Chicago hotel nr Grant Park from $111/nt Chicago's Essex Inn
Up to $400 resort credit: Luxury US hotel stays Waldorf Astoria/Conrad Collection
$99/nt+: Low advance rates at dowtown Chicago hotel Hilton Garden Inn
Baseball Packages from $225 Editors' Review
$173+: Chicago fares from top cites (round-trip) Expedia
$172+: Discount summer fares to NYC (round-trip) Expedia
$49+: Rock-bottom fares to Boston & more (one way) Southwest Airlines
$10/day+: Cheap car rentals from major US airports CarRentals.com