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
4-Diamond Chicago Hotel from $119/Night Editors' Review
Grand-Opening Rates at Chicago Hotel from $89/Night Editors' Review
$98+: Boutique Downtown Chicago Hotel w/Free Breakfast Hotel Blake Chicago
$105+: Stay at the Four Points by Sheraton Chicago Downtown Four Points by Sheraton Chicago Downtown
$58+: Discounted Rates on 3.5-Star Hotels in Chicago-Area Hotwire.com
$39+: Affordable Top-Rated 3-Star Hotels in Chicago-Area Hotwire.com
$138+: Chicago 3-Night Vacations w/Air, Save over 30% Travelocity
$324+: Budget-Friendly Chicago Airport Hotel w/Air & 3-Nts Expedia
$414+: Downtown Hotel Indigo Chicago w/Airfare & 3 Nights Expedia
$466+: 3-star Club Quarters, Wacker at Michigan Expedia
$470+: 4-star The Palmer House Hilton Expedia
$475+: 3-star Doubletree Hotel Chicago Magnificent Mile Expedia
$206+: Albany, GA to Chicago, IL (round-trip) Major Airlines
$429+: Chicago, IL from Anchorage, AK (round-trip) Travelocity
$206+: Chicago, IL from Albany, GA (round-trip) Major Airlines
$429+: Anchorage, AK to Chicago, IL (round-trip) Major Airlines