A true metropolis, Chicago is one of the nation’s top travel destinations -- and rightfully so. With some of the world’s best museums, architecture, dining and entertainment options, along with amazing parks, lakefront beaches and the many neighborhoods that form the city’s patchwork of population, there’s as many reasons to visit Chicago as there are steps and windows in the Willis Tower.
First time visitors to Chicago (we don’t ever call it Chi-Town) will want to spend at least a couple days exploring the Loop’s architecture, the Magnificent Mile shopping spots and the many downtown open spaces – Millennium and Grant Park are must-sees, which lead you right into the Museum Campus with the Field Museum, Adler Planetarium and the Shedd Aquarium. Navy Pier is most assuredly a touristy place, but it makes for a good skyline photograph (though the view from the Planetarium is much better).
Repeat visitors should absolutely get on the El and explore some of the neighborhoods that make the city such a rich place – places like Lincoln Park, Wicker Park and Lakeview (home of Wrigleyville) are all just minutes from downtown on the Blue or Red lines.
Nelson Algren called Chicago “an October sort of city even in spring” but there’s really never a bad time to visit – the city’s peak season runs basically from April through November, and then hotel prices drop significantly during the chilly winters, making it a great time to visit on a budget.
Visitors will likely feel obligated to sample a deep-dish pizza – and they should, at least once – but too many people leave the city without sampling its true culinary gem, the Italian beef. Don’t make that mistake. (There’s also lots of good thin-crust pizza here, too, for whatever it’s worth.)
Top Chicago Hotels Deals
One of Chicago's Top 10 Hotels, Save 45%
The James Chicago • River North, Chicago
Most dates through Dec. 29
Chicago: Summer Stays at Historic Hotel near Mag Mile
Millennium Knickerbocker Chicago • Streeterville, Chicago
Sunday-Thursday in July-August; weekends are +$30-$60
Chicago Loop: 4.5-Star Kimpton Gray Hotel incl. Weekends
The Kimpton Gray • Chicago, IL
Travel options through February
Fourth of July Weekend at Newly-Renovated Talbott Hotel
Talbott Hotel • Near North, Chicago
June 30 - July 7
$128 & up
W Hotels for Upscale City Breaks
SPG Hotels & Resorts • Cities nationwide
Member Favorite Streeterville Hotel w/$27 in Exclusive Extras
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile • Streeterville, Chicago
Chic Gold Coast Hotel w/$50 in Exclusive Extras
Thompson Chicago • Gold Coast, Chicago
Chic 4.5-Star Hotel w/$15 in Exclusive Extras
Chicago Athletic Association • The Loop, Chicago
Boutique 4.5-Star Hotel w/$20 in Exclusive Extras
IVY Boutique Hotel • Streeterville, Chicago
Luxurious River North Hotel w/$50 in Exclusive Extras
Trump International Hotel & Tower Chicago • River North, Chicago
The Loop Hotel w/Exclusive Extras
Club Quarters Hotel, Wacker at Michigan • The Loop, Chicago