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
$69+: Chicago hotel on Magnificent Mile Hotwire.com
Up to 40% off: Recently renovated 4-star hotel in Chicago Booking.com
35% off: Four-star Chicago hotel nr top attractions Booking.com
30% off: Modern hotel in downtown Chicago nr Magnificent Mile Booking.com
$69/nt+: Chicago hotel nr theater district & shopping Booking.com
Pampered Pets Getaway Package from $279/Night Editors' Review
$134/nt+: Chicago hotel w/room upgrade & late check-out Perfect Escapes
$109/nt+: Renaissance Oak Brook Hotel & more Chicago offers Marriott International Central
$76/nt+: Dallas hotel w/restaurant & fitness center Hotels.com
$103+: Low nationwide holiday flight sale (round-trip). United
$152+: Round-trip fall/winter fare sale to over 30 cities Expedia
$14+: Low daily car rentals in NYC, Miami & more Hotwire
$10/day+: Cheap car rentals from major US airports CarRentals.com
$542+: Chicago 3-nt trip at modern hotel w/health club Hotel Arista at CityGate Centre
$325+: Chicago 3-nt stay nr shopping w/air from NY Westin Lombard Yorktown Center