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
Spring and Summer at a Chic Lincoln Park Hotel, 50% Off
Hotel Lincoln • Lincoln Park, Chicago
Travel options through December
$99-$119: 'Modern, Stylish' Hotel Allerton on the Mag Mile
Warwick Allerton Hotel Chicago • Magnificent Mile, Chicago
Travel through September 7
Summer on the Mag Mile, Save 35%
Millennium Knickerbocker Chicago • Streeterville, Chicago
Travel options through July
River North 5-Star Hotel w/$50 in Exclusive Extras
Trump International Hotel & Tower Chicago • River North, Chicago
Streeterville Hotel w/$27 in Exclusive Extras
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile • Streeterville, Chicago
The Loop 4.5-Star Hotel w/$15 in Exclusive Extras
Chicago Athletic Association • The Loop, Chicago
The Loop Hotel w/Exclusive Extras
Club Quarters Hotel, Wacker at Michigan • The Loop, Chicago
Gold Coast 4-Star Hotel w/$50 in Exclusive Extras
Thompson Chicago • Gold Coast, Chicago
Streeterville 4.5-Star Hotel w/$20 in Exclusive Extras
IVY Boutique Hotel • Streeterville, Chicago