$27 Flights to Chicago, IL

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Prices were available within the past 7 days and starts at $27 for one-way flights and $54 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

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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.

Frequently asked questions

Where can I learn more about changing or cancelling my flight to Chicago?
For more information about updating your flight to Chicago or cancelling it, head over to our Customer Service Portal.
How do I find cheap flights to Chicago that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight you select. When you’re searching for flights to Chicago, you’ll see a “no change fees” filter for you to select.
Can I fly to Chicago now?
To get the up-to-date facts about flights in to Chicago, visit the Covid-19 Travel Advisor. Here, you’ll learn about any current travel restrictions and if you’ll be required to go into quarantine after you arrive.
What is the name of Chicago's airport?
Many travelers like to fly into O’Hare Intl. Airport (ORD) when visiting the lively city of Chicago. However, there are a couple of airports here, so keep that in mind when finalizing your flights.
How far is ORD from central Chicago?
ORD is 16 mi from downtown Chicago, so expect a decent commute into the city.
What airport is best to fly into Chicago?
Hop off the plane at O’Hare Intl. Airport (ORD) and you’ll find yourself 16 mi from downtown. MDW also welcomes many people to Chicago. It’s 9 mi from the city center.
How many airlines fly to Chicago?
There are 47 air carriers that fly into Chicago from 249 airports across the globe.
Which airlines fly to Chicago?
American Airlines, United Airlines and Delta Air Lines fly the most frequently to Chicago. The highest number of flights arrive here from New York, with American Airlines having the most services on this route.
How many nonstop flights are there to Chicago?
Flying to a new place is much more fun when there aren’t any lengthy stopovers. If you’re off to Chicago, the great news is that there are roughly 8,345 direct flights each week.
Where are the most popular flights to Chicago departing from?
Flights to Chicago departing from Clinton, Hudson and Georgetown airports are highly sought after.
How long is the flight to Chicago Airport?
Which airport you depart from determines how long you’ll be strapped into your seat. From Clinton to Chicago, the average flight time is 2 hours and 25 minutes. From Hudson it usually takes 2 hours and 4 minutes, and from Georgetown it’s 2 hours and 14 minutes.
How to book the cheapest flight to Chicago?
Don’t leave locking in your flight to Chicago until the last possible moment. That’s one trick well-versed travelers use to get the best deals. Booking well in advance means more choices and less expensive flights. Another excellent way to grab the most affordable fare is to compare all options. If your destination has multiple airports, be sure to research the cost of flying into a less busy terminal. And finally, don’t forget that it’s first in, best dressed. Know what a typical airfare costs and be ready to secure your seat as soon as you spot a bargain. The sweetest deals never last long.
How to survive the flight to Chicago?
We’ve got the lowdown on how to make your flight as pain-free as possible. Follow our tips and you’ll be zooming through airport security and seeing the best of Chicago in next to no time.What to pack in your hand luggage:

  • First things first, pack your passport, official ID, credit cards and medications. Next, you’ll need some in-flight entertainment to while away the time. A juicy novel and a laptop filled with your favorite movies are some great options. If you hope to take a short snooze, a comfy neck pillow and some earplugs will also come in handy. Finally, leave some space for a toothbrush and some cleansing wipes to ensure you arrive at your destination looking fresh and ready to go.

Do not pack the following items in your hand luggage:

  • Make sure you don’t have sharp objects (like a knife or scissors) hiding in the bottom of your carry-on luggage. Other prohibited items include explosive or flammable substances, such as aerosol cans and fuel, and gels and liquids in containers with a volume of more than 3.4 ounces (100 milliliters).

What to wear on a flight:

  • Comfort should be your priority when choosing what to wear on your flight. Consider your footwear choice with care too, as swelling of the feet and ankles are a common occurrence. Roomy, closed-toed shoes are your best bet.
  • The result of sustained periods of immobility, deep vein thrombosis (DVT) is a blood clot condition that can affect passengers during long-haul flights. But the good news is there are proven ways to significantly reduce your risk of developing it. Stay hydrated, get up and wander the aisles wherever possible and wear compression socks to help improve your circulation.

How to get through airport security fast when flying to Chicago?
As seasoned travelers know, the secret is to be organized before you arrive at the airport security gate. That way, you’ll be boarding that plane to Chicago in next to no time. Follow these tips and get your vacation off to a flying start:

  • Be sure to keep your ID and boarding pass within close reach. They’re the first items you’ll be asked for by airport security.
  • Time to strip down. Well sort of. Your jacket, belt, keys and other small items, like your headphones, will need to go on a tray through the X-ray machine. Make the whole process easier by removing them as it gets closer to your turn.
  • Electronic devices like phones and laptops will also have to go through the machine for inspection. Don’t worry, you’ll be back online soon enough.
  • Want to bring along your favorite hand cream? Not a problem. As long as the volume is no larger than 3.4 ounces (100 milliliters) and it’s stored in a zip-lock bag, you’re permitted to bring it with you in your carry-on bag.
  • There’s a possibility that you’ll be asked to remove your shoes to be X-rayed, so wearing slip-on sneakers is always a wise idea.
  • Airlines won’t allow any sharp objects in your carry-on luggage. If you need to bring these kinds of items, check them in.

Flights to Chicago information
Destination AirportO'Hare Intl.
Destination Airport IATA CodeORD
Destination City NameChicago
Flight Price$53

Trending flights to Chicago

Prices were available within the past 7 days and starts at $27 for one-way flights and $54 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

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