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How to find cheap flights to Chicago?

The cheapest prices found with in the last 7 days for return flights were C$117 and C$233 for one-way flights to Chicago for the period specified. Prices and availability are subject to change. Additional terms apply

Origin Destination Travel Dates Flights From*
LGA Chicago 14 Sep. - 21 Sep. C$117
LAX Chicago 20 Jul. - 22 Jul. C$212
*Prices include taxes and fees
Origin Destination Travel Dates Flights From*
DFW Chicago 25 Jun. - 27 Jun. C$327
*Prices include taxes and fees

Your guide to flights to Chicago, IL

United, American Airlines fly to Chicago, so use Travelocity to search, find, and compare some truly tempting deals from the 2 airlines—that way you can be sure you’ve found the best deal for you. A flight to Chicago IL currently costs between C$117 and C$409. Prices vary, but for the best fares, travel in December when prices are at their lowest.  

Top tips for finding cheap flights to Chicago  

The cheapest flight for a round trip to Chicago is currently C$117. When you search for flights to Chicago, enter your preferred travel dates then click on ‘flexible dates’ to compare cheap flight tickets to Chicago for nearby days.  The cheapest month to travel to Chicago is July from our list of deals available.  

But if you’re flexible about when you travel, you can find great deals on flights across the year. If you’re planning a vacation, you can save more on Travelocity when you bundle flights with car rental and hotel bookings, too. Many airlines currently offer flexible booking options, so look for flights offering no change fees.   

How to cancel flights to Chicago 

We know plans change, that’s why at Travelocity, we make it as easy as possible for you to cancel or amend your plane tickets. Go to My Trips, enter your itinerary number, then follow the instructions. Many airlines let you cancel flights online free of charge if you booked it in the last 24 hours. Visit Customer Service for more advice.  

Why you should book your flight to Chicago with Travelocity 

We have top deals on plane tickets even for last minute flights to Chicago, so you can simply type in your travel dates and compare our best prices. Booking with Travelocity means you get flexible cancellation options, 24/7 support, and, thanks to our Price Match Promise, if the airfare drops after you book, you can get a refund! Whether you’re planning a business trip, weekend getaway, or a family vacation—let Travelocity get you to Chicago for less. 

Flights to Chicago: Customer Reviews

Feb 27, 2020

power on all planes would be nice - it is rare that it is not there

Feb 3, 2020

All good

Jan 20, 2020

Baggage delayed

Dec 28, 2019

Flight was perfect thanks

Nov 23, 2019

TV screen not functional

Nov 14, 2019

It would be very helpful if the airline crew would remind passengers to put smaller luggage and backpacks under their seat to leave more space in overheads for larger things. I watched quite a few people have issues with their luggage due to others with small things in the overhead and nothing under their seat. Also, would really appreciate maybe a reminder to passengers of the person behind them when reclining their seat.. there should be an education on that or just remove the feature, sitting with the person in fronts seat back in your face isn't fun.

Nov 10, 2019

Seat power did not work, otherwise flight was fine.

Nov 9, 2019

Baggage took forever upon arrival. I know that is Pearson and not united so I didn’t let it impact my score but T1 is the worst for baggage times

Nov 7, 2019

Staff very friendly and knowledgeable!!

Aug 18, 2019

A little more seat room would be better

May 1, 2019

Check in kiosk was extremely slow

Feb 11, 2019

Very satisfied. Free baggage wouid have been nice but there was always a gentleman to put up my carryon so can't complain. A tastier snack would have been nice.

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FAQs about Chicago Flights

Can I catch a flight to Chicago at the moment?

For the latest complete info regarding passengers on flights bound for Chicago, check out our Covid-19 Travel Advisor. Everything you need to know about current travel restrictions and quarantine requirements is located here in one convenient place.

Which airlines fly to Chicago?

When it comes to airlines that offer flights to Chicago, you're flush with choice. There are 20 companies that operate in this major city. Book your favorite seat on one of these leading carriers:

  • United Airlines
  • American Airlines
  • Southwest Airlines
If I am not able to travel due to COVID-19, can I change my booking to a later date?

For more info about changing your flight to Chicago, please visit our Customer Service Portal.

What airport is best to fly into Chicago?

When looking up flights in and out of Chicago, explore all available options. With a few airports near the city, the price of your tickets may differ depending on which one you select. Here are the most popular of them:

  • O'Hare Airport – 26 kilometers from downtown
  • Chicago, IL Airport (MDW-Midway Intl.) – 14 kilometers from downtown
  • Joliet Park District Airport (JOT) – 60 kilometers from downtown
Where to stay in Chicago

Researching a trip to Chicago? Let Travelocity help you create some extraordinary new memories. You'll find 4,256 instantly bookable accommodations to choose from on our site.

Indulge in a bit of luxury at the Palmer House a Hilton Hotel or the Silversmith Hotel Chicago Downtown. After all, it's not every day you take a vacation! However, if you don't think you'll spend much time in your suite, how about a cheaper option like the HI Chicago or the Travelodge by Wyndham Downtown Chicago?

Fancy staying close to McCormick Place? Now's the time! Both the Hyatt Regency McCormick Place and the Marriott Marquis Chicago are comfortable places and are just a walk away.

Places to visit in Chicago

With so many unmissable attractions in Chicago, you might just have to let the boss know that you need an extra week off. Begin with Art Institute of Chicago, and Millennium Park. You'd also be nuts to miss out on seeing Skydeck Ledge, and Willis Tower.

Experience the fabulous flavors of this lively metropolis by enjoying places like Chicago Cultural Center, and Buckingham Fountain. If you want more options, Merchandise Mart, and Wrigley Building are worth a look too.

If you are a fan of theater, be sure to take in a play at Chicago Theatre. Like some more options? Many of the best tourist attractions are situated in Chicago Riverwalk area. But that's not all. Venture to Water Tower Place and look up. You'll be thrilled by how grand this building is.

How to get through airport security fast when traveling to Chicago

Make your flight to Chicago a little bit easier by following these helpful tips and pointers:

  • Security staff will expect to see your travel ID and boarding pass as part of their checks. Store them in an accessible place, so they're ready for inspection.
  • Wallets, belts and mobile phones should be put in a tray for X-raying. If you pass through the body scanner with these items, you'll be turned back and instructed to remove them.
  • Electronic items such as tablets, laptops and phones are always sent through the X-ray machine separately. Make sure they're easily accessible.
  • When you get to the security checkpoint, you'll be asked to place all creams, gels and liquids in a separate tray for scanning. Make sure they're all stored in containers smaller than 3.4 ounces (161 kilometerslliliters) and sealed in a clear zip-lock bag.
  • Untie your shoelaces before approaching the body scanner. Depending on what sort of shoes you're wearing, security may instruct you to remove them.
  • Pocketknives and corkscrews are not permitted on board the aircraft. Pack them in your checked luggage to avoid forfeiting them at the security checkpoint.

Flights To Chicago

Each time you visit Chi-Town, you’ll fall in love anew. Even if you’ve stood in front of the famous metallic bean and stood along the Navy Pier, you won’t be left wanting for original ways to spend your time. As Mark Twain posited, “She is novelty, for she is never the same Chicago you saw when you passed through the last time.” The modern city on the shores of Lake Michigan is always evolving and will never fail to enchant you. Between the exciting sports culture and buildings that hearken back to a time when Frank Sinatra and Al Capone ran the scene, Chicago always impresses.

Flights to Chicago depart from tons of destinations; just sit back, start dreaming of deep-dish pizza, and before you know it you’ll be touching down in the Windy City. Book your airfare on Travelocity today, and you’ll save enough cash to afford all the famous frankfurters you want.

Transportation from Chicago Airports

Chicago flights land at one of the two major airports: O’Hare International Airport (ORD) and Midway International Airport (MDW). Getting to downtown Chicago from ORD is a breeze when you take the Blue line train, which is part of the Chicago Transit Authority train system. From MDW, jump on the Orange line train.

If you’re not staying downtown, buses are available to most parts of the city from both airports. When a private ride is more your style, hail a taxi outside the baggage claim area. Many hotels also have shuttle buses that will take you to and from the airport. But if independence is more your style, there are many rental car companies located within the airport if you need your own wheels; book your ride when you purchase your airfare to Chicago and your vacation is set.

Hotels Near ORD and MDW

A savvy traveler such as yourself is sure to purchase one of our top flight deals to Chicago. Not only will you travel on one of the most affordable and convenient flights, but you’re wise enough to book a Chicago hotel befitting of your fine taste:

  • The Palmer House Hilton: This hotel bills itself as hip and historic, and one step inside the lobby lets you know the description is spot on. Opulent ceilings and marble accents remind you of an era when dinner was always a formal affair, while the rooms are adorned in bright furniture and clean modern lines.
  • Wyndham Grand Chicago Riverfront: From the cocktails served fireside at Hoyt’s Patio to in-room massages, this downtown hotel is designed to pamper. Get a room with a view and overlook the Windy City from the moment you wake up, and let the concierge help you book excursions to Chicago attractions.
  • Hyatt Regency Chicago: This four-diamond hotel is connected to the Illinois Center downtown, right in the heart of the city. You’ll be just a short and leisurely walk from the Magnificent Mile and Grant Park.
  • Congress Plaza Hotel: Legendary hotels are just your style, so this Grant Park hotel has your name on it. Enjoy a view of Lake Michigan from your room, and revel in the property’s storied history, which dates back to 1893.

Things to Do in Chicago

The Windy City is known for its pizza and beloved sports teams, but the Midwest powerhouse packs a cultural punch and can impress even seasoned world travelers. Begin your exploration with an investigation of Millennium Park, and then get a taste of Chi-Town’s creative offerings at the Art Institute of Chicago. From the observation deck of the Willis Tower, you can spot your favorite attractions and plot your route of the city. Like the savvy tourist you are, you booked cheap plane tickets to Chicago. Go ahead, buy entrance to the Lincoln Park Conservatory and Brookfield Zoo.

Use Travelocity to search through the flight options to the Windy City. Once you find one of the cheapest flights to Chicago and buy your tickets, there is nothing left to do but start dreaming of mozzarella and pack your bags. Chi-Town is waiting to welcome you with open arms and delight you with its Midwest charms.

How to find cheap flights

What is the best day to buy a plane ticket?

Airfares offered on Wednesdays tend to be the cheapest, according to flight demand on Travelocity.ca in 2020. Purchasing your airfares on a Thursday or Friday can also provide better value, however our advice if you’re looking to save money is to avoid booking on a Saturday. Our data shows, the start of the weekend has the highest ticket values on average, so keep this in mind if you’re browsing flight deals on a weekend.


What are the cheapest days to fly?

Frequent travellers may already know this, but earlier in the week is often the cheapest time to fly. Flights departing on a Tuesday are the cheapest of the week. Since weekend flights tend to be more popular, this causes the prices to rise which is why on average. Airfares booked on Travelocity.ca in 2020 were most expensive for Saturday departures.


How far in advance can you book a flight?

Here’s the deal: It is typically possible to start comparing international airfares on Travelocity.ca up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2020 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 2 weeks to 3 months prior to their travel dates.


How can I save money on airline tickets?

We'll let you in on a secret...You can save big on flights if you mix and match your airlines and fare types. In fact, travellers who booked flights on Travelocity.ca in 2020 saved close to 60% when their return flights consisted of two different airlines or fare types.

*According to flight demand on Travelocity.ca from January to December 2020. Savings are subject to change and may vary depending on selections made.

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.