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How much is the cheapest round-trip flight to Chicago?

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

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Flights to Chicago information

Destination Airport O'Hare Intl.
Destination Airport IATA Code ORD
Destination City Name Chicago

Chicago Flights

Chicago Airports

When youíre looking to book flights to Chicago, Illinois, there are two airports that serve the Windy City. O'Hare International Airport is the main one, while Chicago Midway International Airport is considered the secondary tarmac.

O'Hare sits 17 miles northwest of the Loop. It provides plenty of amenities to keep you entertained while you wait for your flight or transportation into Chi-Town. If youíre hungry, youíre in luck. This airport boasts a variety of restaurants and cafes, providing sit-down cuisine and meals-on-the-go. The airport also features various shops, where you can find Chicago souvenirs, designer goods, electronics, and duty-free products. To top it all off, O'Hare provides spa services and even a yoga room to help keep you relaxed and rejuvenated during your travels. Find out additional information about O'Hare on Flights.com.

Located roughly 12 miles northwest of downtown Chicago, Midway Airport includes several shops, the majority of which are located in the Midway Boulevard. You can also find restaurants, snack shops, and fast-food options when youíre looking fuel up before or after your flight. While youíre traveling through the airport, look for the public art and installation collections throughout the terminal.

Airport Transportation

When you have Chicago flights, rest assured knowing that both airports provide ground transportation. Here at Expedia.com, you can reserve Chicago car rentals and pick up your vehicle at your preferred airport. Alternatively, you can take advantage of public transportation as the Chicago Transit Authority provides both train and bus service to Midway and OíHare. Other transportation options include taxis, shuttles, and limousines.

Chicago Activities

Once youíve decided itís time to book plane tickets to Chicago, IL, start planning your adventures. The Windy City is home to fascinating exhibits, from the galleries at the Museum of Contemporary Art to the artifacts at the Chicago History Museum. For some of the best views of the skyline, venture up to the 360 Chicago observatory deck in the John Hancock building or the Skydeck Chicago in the Willis Tower. While youíre in town, chow down on some famous deep-dish pizza or Chicago-style hot dogs for an authentic taste of the city. Then round out your day with reservations at one of the best hotels in Chicago.

Planning Your Trip

The best times to visit Chicago are between April and May and September and October. Temperatures are moderate during these months, and the high season hasnít hit yet. Summertime is considered the most popular time to visit, so you may face more crowds and more expensive rates during this season. Meanwhile, winter brings temperatures in the low 30s F and a high chance of snowstorms.

Regardless of when you plan to visit, Expedia.com is here to match you with cheap flights to Chicago. Sort through our selection to find discounts on round-trip tickets that suit your price range. You can even use our mobile booking app for convenient access to exclusive online deals on airfare to Chicago. Book your affordable flights right here and start getting a taste for that delicious deep-dish pizza.

How to save money on your Hawaiian trip?

One surefire way to save money on your Hawaiian trip is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free!

Book a package for your Hawaiian trip now & unlock savings up to 42% off selected hotels! Terms apply.

Hawaii Vacation Deals


How to find cheap hotels in Hawaii?

When it comes to finding cheap Hawaii hotels, the best time to do it is during low season or shoulder season, which ranges between late January to May.

During this time, you’ll enjoy lower hotel rates, less crowded hotels, and even though you might get some rain, most of the showers in Hawaii are followed up with gorgeous rainbows!

Hawaii Hotel Deals


What are the top things to do in Hawaii Island?

From sinking to the bottom of the ocean on a submarine to soaring into the skies to discover the world's most geologically active environment from a helicopter, there's no end to the activities that Hawaii Island has to offer.

Check out what are some of the top things to do in Hawaii that is highly recommended by fellow travelers!

Top Things to do in Hawaii Island


When is the best time to buy airline tickets?

From America, regardless of destination, average ticket prices for economy and premium cabins tend to rise as the departure date gets closer. Waiting to book at the last minute can be an expensive gamble. Booking three weeks ahead of a trip is the “sweet spot” for fare savings.

Furthermore, travelers can unlock discounts on the total cost of a trip when they bundle flights and hotel stays, and in some cases with other travel products and experiences. For example, adding a flight to an existing hotel booking through Expedia can result in hotel savings of up to 42%. Terms apply.

Hawaii Package Deals


Where to stay in Big Island Hawaii?

Start planning your Big Island vacations by uncovering the best place to stay in Hawaii. Though you won’t find the bustling city atmosphere of Honolulu, Big Island hotels offer a distinctly Polynesian charm.

If you’re looking for a world-class experience in an unbeatable location, head to the luxury hotels near Hilo, which are close to Rainbow Falls, Lili'uokalani Gardens, and the Kaumana caves.

Browse luxury hotels in Hilo