Best Deals to Chicago Last modified: Oct 15, 2018 4:15 -04:00Prices shown were found by travelers like you over the past 30 days
We've scanned 48,195,047,545 round trip itineraries and found the cheapest flights to Chicago. American & United frequently offer the best deals to Chicago flights, or select your preferred carrier below to see the cheapest days to fly.
Chicago, also known as the Windy City, draws visitors from around the globe in search of world-class shopping, museums, improv comedy, and the finest deep dish pizza in all the land. Whether you are visiting on business or for pleasure, it is a city that you fall in love with, with its gorgeous skyline, beautiful Michigan Lake shore, cultural richness, convenient Midwest location, a cozy-yet-big-city feel, and overall hospitality. Your options are endless when visiting this city, so we've highlighted a few pointers below for your trip.
Chicago is a true Midwestern treasure; a bustling metropolitan city with beautiful architecture, an outdoorsy feel, great nightlife and some of the best food in the country. No matter who you are, you'll find a neighborhood where you fit right in, let alone places you'll love to explore. Whether you get to spend time on the lakefront beaches in the summer or enjoy the city during the snowy winters, Chicago has you covered.
CTA (the Chicago Transit Authority), Chicago's public transportation, allows you to get around easily without a car, just don't ask a Chicagoan whether the Red Line is better than the Blue Line. You could spend weeks in Chicago without seeing a small fraction of what the city has to offer. Below are a few attractions that are definitely worth checking out.
The Art Institute of Chicago: Sitting among the world's best art museums, it is home to pieces from masters throughout the ages including Picasso, Matisse, Dali, Seurat, Hopper, and Warhol.
Navy Pier: The Pier puts you right on Lake Michigan, next to Grant Park and landmarks like Millenium Park and Buckingham Fountain. You can shop, eat, listen to live music and check out the Tony Award-winning Chicago Shakespeare Theater.
The Second City: For decades, Second City has been a breeding ground for actors and comedians who eventually end up on Saturday Night Live, in major movies, or on primetime television. Catch one of their latest shows to see the next generation of great improv artists.
Music Box theatre: This is a go-to place for late midnight entertainment.
Shopping and Restaurants in Chicago
Chicago is famous for its food. You can find everything from celebrity chef-run restaurants to small storefronts that serve up the finest Polish sausage out there. If shopping is more your thing, you'll have no problem finding some places to spend your money.
The Magnificent Mile: The Mag Mile attracts tourists from all over the world. This section of Michigan Avenue is lined with high-end retail shops, couture clothing, and restaurants.
Chinatown: Chicago's Chinatown, located in Armour Square, is home to shops, restaurants, festivals, and a range of cultural events. For a dinner-and-dim sum spot, try Cai. For ramen noodle lovers, don't miss the Strings Ramen Shop with their own noodle-making Japanese machine in the basement.
State Street Retail Historic District: State Street offers a bit more of a relaxed atmosphere than you'll find on the Magnificent Mile, but there's still plenty of shopping to be done. You'll find boutique clothiers, massive retailers, and more.
Boystown: Also known as East Lakeview and recognized as Chicago's gay village, this eclectic, bubbly neighborhood can't be missed. It is situated in a perfect spot in Chicago, southeast of Wrigleyville, bordered by Lake Michigan, Clark Street, Irving Park and Diversey Avenue. Grab a famous milkshake from the vegetarian and vegan Chicago Diner, as you walk by boutique shops and some of Chicago's best restaurants and nightlife. You'll notice many shops with a water bowl outside their door for your pet, and they'll give out treats too!
Flights to Chicago
Chicago's has two major commercial international airports, O'Hare and Midway. These airports provide travelers with a wide range of options when it comes to airlines, routes, and cheap flights to Chicago. If the expansion that many hope for actually takes place at Gary-Chicago International Airport, travelers in the Chicago and area could see a third major commercial travel airport in the future.
O'Hare International Airport (ORD): O'Hare remains one of the busiest and most well-known airports in the world. It serves as a hub for United Airlines, and it functions as a gateway to domestic and international destinations for travelers from across the U.S. If you travel to O'Hare and don't feel like springing for a taxi, head to the Blue Line of the "L" and take the train into the city.
Midway International Airport (MDW): Located on the southwest side of Chicago and serving as one of Southwest Airlines' major airports, Midway is a smaller, viable, and some would say more convenient, alternative to O'Hare. It is located only eight miles from the Loop. You can take the short hike to the Orange Line, which connects with the rest of the city.
Don't forget to walk or go on a bike ride along the lakefront. Regardless of the type of trip you're planning, you won't regret it if you choose Chicago as your destination.
Popular flights to Chicago
- From Boston to Chicago$77RTGOOD10/17 - 10/20
- From Atlanta to Chicago$111RTGOOD10/27 - 10/31
- From New York City to Chicago$113RTGOOD10/23 - 10/24
- From Las Vegas, Nevada to Chicago$121RTGOOD10/17 - 10/23
- From London, United Kingdom to Chicago$289RTGOOD11/16 - 11/24
- From Beijing to Chicago$514RTGOOD10/16 - 10/28