Hotels in Chicago start at $40 per night. Prices and availability subject to change. Additional terms may apply.
Kirsten Maxwell Gnational Gnomad
Chicago has two major international airports: O’Hare (ORD), which is 17 miles northwest of downtown and Midway (MDW), just 10 miles southwest of the city. Transportation from both of these locations is plentiful and comes in the form of city trains, taxis, and rental cars. Expect it to take anywhere from a half hour to an hour to reach downtown, depending on the time of day. It is also possible to arrive via Amtrak. The main train depot—Union Station—is in the heart of the city.
Most major attractions are located in the heart of downtown. The city is perfectly manageable using public transportation, taxis, Uber/Lyft, and your own two feet. Chicago Transit Authority (CTA) operates the buses and trains, and METRA runs trains to the outlying suburbs. If you want to explore the area on your own time, consider renting a car.
TIP: Chicago traffic can be stressful—especially during rush hour, on the weekend, and during major sporting events or festivals. Summer is construction season, and you’ll see plenty of snow during the winter. If this concerns you, stick with public transportation.
For a true overview of the city, head up. Both the Willis Tower and 360 Chicago offer fantastic views of the city from towering heights. The has “The Ledge,” a glass box that extends out from the building, allowing unobstructed views of the city 1,353 feet below. Still haven’t quenched your thirst for heights? Head to , located in the John Hancock Center, and check out “Tilt.” Visitors enter a glass cage that tilts away from the building and gaze out over the city from a height of over a thousand feet. Neither experience is for the faint of heart!
The Art Institute of Chicago was named the top museum in the world by Trip Advisor in 2014, and it houses one of the largest permanent collections in the United States. Some of the featured artists include Picasso, Monet, and Rivera, but there are thousands more to admire.
Millennium Park is centrally located parallel to Michigan Avenue and Lake Michigan, and it’s the perfect place to gather with a group of friends. During the summer there are free concerts, performances, and festivals, and during the rest of the year it is a great place to relax and people-watch. The main attraction is the “Cloud Gate” sculpture. Most Chicagoans refer to it as “The Bean” because it looks like, well, a giant silver bean. Chicago’s skyline reflects from all its shining sides, and you can even walk underneath the sculpture.
Adjacent to this is the Crown Fountain. The fountains are actually two 50-foot towers that display images of Chicago residents on a giant video screen. When the face on the screen smiles, water comes pouring from their mouth, dousing the eager children gathered below.
Between Millennium Park and the waterfront is the beautiful Maggie Daley Park. With playgrounds for all ages, an ice skating ribbon in the winter, and a rock climbing wall, it is a magical escape in the city for families.
It’s hard to miss the 26 miles of Lake Michigan shoreline that borders downtown Chicago. The beaches are open to the public, so find a beach near your hotel, grab your towels, and walk or take a taxi to the shoreline of your choice. Montrose Beach, North Avenue Beach, and Oak Street Beach are all worth a visit.
Chicago is a city made for foodies—there’s almost too many good restaurants to list. Obvious choices for deep dish pizza are Giordano’s, Pequod’s, and Lou Malnati’s. Craving a Chicago dog? Head to Portillo’s and be sure to grab a slice of chocolate cake for dessert. Want to try one of the better restaurants in town? Find something owned by Rick Bayless (Xoco, Frontera Grill), the Boka Group (Girl & The Goat, Boka), or Paul Kahan (The Publican, Big Star) —you won’t be disappointed. Don’t forget to try multiple servings of the cheese and caramel popcorn (Chicago mix) at Garrett Popcorn, because there is nothing like the original.