$252 Cheap Flights from Tyler (TYR) to Chicago (ORD)

View $252 flight on Wed, Sep 3, 2025Opens in a new window

Popular airlines from Tyler, TX (TYR-Pounds Regional) to Chicago O'Hare Intl. Airport (ORD)

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Cheap Flights from Tyler to Chicago (TYR-ORD)

Prices were available within the past 7 days and start at $252 for one-way flights and $357 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Thu, Sep 25 - Tue, Sep 30
TYR
Tyler
ORD
Chicago
$357 Roundtrip, found 9 hours ago
$357
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Thu, Sep 25 from Tyler to Chicago, returning Tue, Sep 30, priced at $357 found 9 hours ago
American Airlines
Tue, Sep 23 - Tue, Sep 30
TYR
Tyler
ORD
Chicago
$371 Roundtrip, found 3 days ago
$371
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Sep 23 from Tyler to Chicago, returning Tue, Sep 30, priced at $371 found 3 days ago
American Airlines
Tue, Sep 23 - Tue, Sep 30
TYR
Tyler
ORD
Chicago
$372 Roundtrip, found 3 days ago
$372
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Sep 23 from Tyler to Chicago, returning Tue, Sep 30, priced at $372 found 3 days ago
American Airlines
Tue, Sep 23 - Tue, Sep 30
TYR
Tyler
ORD
Chicago
$380 Roundtrip, found 3 days ago
$380
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Sep 23 from Tyler to Chicago, returning Tue, Sep 30, priced at $380 found 3 days ago
American Airlines
Thu, Sep 25 - Tue, Sep 30
TYR
Tyler
ORD
Chicago
$382 Roundtrip, found 9 hours ago
$382
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Thu, Sep 25 from Tyler to Chicago, returning Tue, Sep 30, priced at $382 found 9 hours ago
American Airlines
Tue, Sep 23 - Tue, Sep 30
TYR
Tyler
ORD
Chicago
$384 Roundtrip, found 3 days ago
$384
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Sep 23 from Tyler to Chicago, returning Tue, Sep 30, priced at $384 found 3 days ago
American Airlines
Tue, Sep 23 - Tue, Sep 30
TYR
Tyler
ORD
Chicago
$385 Roundtrip, found 3 days ago
$385
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Sep 23 from Tyler to Chicago, returning Tue, Sep 30, priced at $385 found 3 days ago
American Airlines
Tue, Sep 23 - Tue, Sep 30
TYR
Tyler
ORD
Chicago
$389 Roundtrip, found 3 days ago
$389
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Sep 23 from Tyler to Chicago, returning Tue, Sep 30, priced at $389 found 3 days ago
American Airlines
Tue, Sep 23 - Tue, Sep 30
TYR
Tyler
ORD
Chicago
$389 Roundtrip, found 3 days ago
$389
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Sep 23 from Tyler to Chicago, returning Tue, Sep 30, priced at $389 found 3 days ago
American Airlines
Tue, Sep 23 - Tue, Sep 30
TYR
Tyler
ORD
Chicago
$390 Roundtrip, found 9 hours ago
$390
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Tue, Sep 23 from Tyler to Chicago, returning Tue, Sep 30, priced at $390 found 9 hours ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $492
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $492
Flights from Tyler (TYR) to Chicago (ORD)
Origin airport
Pounds Regional
Destination airport
O'Hare Intl.
Airlines serving
American Airlines
Roundtrip price
$357
Distance
782 mi

Tyler to Chicago Flights

The cheapest times to fly from Tyler to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Tyler to Chicago are during the month of September. You can find some of the cheapest flights from Tyler to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Tyler to Chicago

Sunday is one of the best days to book for cheap flights from Tyler to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Tyler to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Tyler to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $252 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Tyler to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Tyler to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Pounds Regional Airport (TYR) to O'Hare Intl. Airport (ORD) cost?
Grab a cheap one-way flight from $252 or cheap return flight from $357 from Pounds Regional Airport (TYR) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Pounds Regional Airport (TYR) to O'Hare Intl. Airport (ORD)?
Flying in September is a great way to save, as it's the cheapest month for flights between TYR and ORD. You'll typically find the lowest prices during the off-season.
What is the cheapest airline that flies from Pounds Regional Airport (TYR) to O'Hare Intl. Airport (ORD)?
To find the cheapest airline that'll fly you from TYR to ORD, use Expedia's filter tool. Tailor your search based on your travel needs, such as preferred carriers and seat class. You can then sort your results by "Price (lowest to highest)" to see the cheapest fares upfront.
How many flights per day from Pounds Regional Airport (TYR) to O'Hare Intl. Airport (ORD)?
You'll have to catch a flight with a layover when traveling from Pounds Regional Airport (TYR) to O'Hare Intl. Airport (ORD). There are no daily direct flights on this route. However, just filter your search to include one or two stops to discover an option that works for you.
What day of the week has the most flights from TYR to ORD?
Generally you'll find the most flight options available on a Friday. Tuesdays are often the quietest.* But this can vary depending on the time of year, carrier and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Pounds Regional Airport (TYR) to O'Hare Intl. Airport (ORD)?
To avoid possible delays on the Pounds Regional Airport (TYR) to O'Hare Intl. Airport (ORD) route, travel before 3 PM. Departures after this hour are 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Pounds Regional Airport (TYR) to O'Hare Intl. Airport (ORD) last-minute?
Last-minute bookings from TYR to ORD are typically more expensive. To lock in the cheapest rates, start looking for flights well in advance. That being said, if you're flexible with your travel dates, you may land a cheap ticket just before your departure.
Is it cheaper to book a TYR to ORD flight and hotel package?
Compared with arranging hotels and flights separately, booking a TYR to ORD flight and hotel package with Expedia could lead to significant savings. Better still, managing everything in one place will take the hassle out of planning your trip. Just pick your flights and choose from our extensive range of hotels, then tailor your trip with other add-ons like car rentals and activities.
Can I cancel or change the date of my flight from Pounds Regional Airport (TYR) to O'Hare Intl. Airport (ORD)?
If you reserved your TYR to ORD flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the ticket type you purchased, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal for further details.

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*Available to One Key members.