$27 Cheap Flights to Chicago , IL

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How much is the cheapest flight to Chicago?

Prices were available within the past 7 days and start at $27 for one-way flights and $53 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 canceling my flight to Chicago?
Most flights are free to cancel within 24 hours of making the reservation. However, some flights are non-refundable, and you may receive a flight credit from the airline to use for a future booking. For more information, please visit our Customer Service Portal.
How do I find cheap flights to Chicago that have flexible change policies?
By using our helpful “No change fee” filter, that’s how. Just enter your origin, destination and travel dates, click the “Search” button, then tick the box underneath the “Flexible change policies” heading (top left-hand side of your screen). Expedia makes it simple to find flexible, low-priced flights to Chicago.
What is the name of Chicago's airport?
Chicago has more than one airport, but most travelers fly into O’Hare Intl. Airport (ORD).
How far is O'Hare Airport from central Chicago?
O’Hare Intl. Airport (ORD) is 16 mi from downtown Chicago, so be prepared for a decent commute into the center of the city.
What airport is best to fly into Chicago?
If you’re jumping on a plane to Chicago, you’ll most likely land at O’Hare Airport (16 mi from downtown). Chicago Airport (9 mi from downtown) is the other main airport that services the city.
How many airlines fly to Chicago?
Chicago is serviced by 45 air carriers from at least 220 worldwide airports.
How many nonstop flights are there to Chicago?
Flying to a new place is much more fun when there aren’t any stopovers to slow you down. If you’re off to Chicago, the great news is that there are approximately 8,086 direct flights operating every week.
Where are the most popular flights to Chicago departing from?
Flights to Chicago from New York, Dallas and Washington airports are in high demand.
How long is the flight to Chicago Airport?
If you’re flying to Chicago from Queens Village, you’re looking at a flight duration of 2 hours and 34 minutes. Those leaving from Washington can expect to be traveling for 2 hours and 5 minutes. From Denver it’s approximately 2 hours and 23 minutes away.
How to book the cheapest flight to Chicago?
Don’t leave locking in your flight to Chicago until the very last minute. That’s one move well-versed travelers use to get the best deals. Booking in advance means more options and cheaper flights. Don’t stop there, though. Do some research and see if there is more than one airport at your destination. Ticket prices often differ depending on which airport you pick. Make sure you compare fares across airlines too. And finally, remember that the early bird catches the worm. Know what a typical airfare costs and have your credit card ready to book your ticket as soon as you see a great bargain. The best deals never last long.
How to survive the flight to Chicago?
If you’re not prepared, airports and flying can be testing. But don’t hit the panic button just yet. Follow these useful tips and enjoy a trouble-free start to your getaway in Chicago.What to pack in your hand luggage:

  • It’s simple — first, pack in your passport, important documents, cash and daily medications. Next, you’ll want some entertainment to while away the time. A thrilling novel and a laptop crammed with your favorite movies are some fantastic options. If you intend to take a short snooze, a quality neck pillow and a pair of noise-canceling headphones will also come in handy. Finally, make room for a toothbrush and some facial wipes to ensure you arrive at your destination looking fresh and raring to go.

Do not pack the following items in your hand luggage:

  • While the list of prohibited items differs between airlines, the general guide to follow is nothing flammable, sharp or explosive. This includes knives, scissors, spray paint and flares. Sporting equipment like bows and arrows, and objects that could harm passengers, such as pepper spray and firearms, can’t come on board with you either.

What to wear on a flight:

  • Your number one priority is to be as comfortable as possible. Layer up with loose, breathable clothing and remember to bring a pullover in case it gets cool in the cabin. Pick a pair of well-fitting, flat shoes as it’s possible that your feet and ankles will swell a little during the journey. Leave the high heels and hiking boots in your checked baggage.
  • The serious condition by the name of DVT (deep vein thrombosis) is a potential risk on long-haul flights. It’s the result of blood clots forming due to poor circulation. Walking up and down the aisle and doing leg and foot exercises while seated is a great way to prevent this from happening. Wearing a quality pair of compression socks or tights is also recommended.

How to get through airport security fast when flying to Chicago?
A little pre-planning before your flight can make your getaway to Chicago easy and painless. Check out our handy tips and tricks for a stress-free journey past security:

  • First things first. Your passport and travel documents will need to be shown to security personnel. Keep them within easy reach to avoid fumbling around for them.
  • Time to strip down. Well kind of. Your jacket, belt, keys and other contents of your pockets, like your headphones, will need to go on a tray through the X-ray machine. Make the whole process faster by removing them as it gets closer to your turn.
  • All your electronic devices, including your tablet and phone, are also required to be separately scanned.
  • Remember to remove gels and liquids from your hand luggage. They often need to be sent through the X-ray separately. Each product should be no larger than 3.4 ounces (100 milliliters) and everything must fit inside a quart-size (one liter), clear zip-lock bag.
  • Lightweight sneakers are a clever footwear choice as you’re less likely to be asked to remove them when passing through security. Safety boots and other heavy shoes are often subjected to additional screening.
  • Sharp or pointed objects (like knives and scissors) can’t be taken on board. They’ll be confiscated at security, so pack them safely away in your checked bags.

Flights to Chicago information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Destination city name
Chicago
Airlines serving
Alaska Airlines, American Airlines, Delta, Frontier Airlines, JetBlue Airways, Spirit Airlines, Sun Country Airlines, United
Roundtrip price
$68
Popular airline
Frontier Airlines

Trending flights to Chicago

Prices were available within the past 7 days and start at $27 for one-way flights and $53 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
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