$109 Cheap Flights from Amarillo (AMA) to Chicago (MDW)

View $109 flight on Wed, Aug 13, 2025Opens in a new window

Popular airlines from Amarillo, TX (AMA-Rick Husband Amarillo Intl.) to Chicago Midway Airport (MDW)

Cheap Flights from Amarillo to Chicago (AMA-MDW)

Prices were available within the past 7 days and start at $109 for one-way flights and $237 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Wed, Nov 12 - Wed, Nov 19
AMA
Amarillo
MDW
Chicago
$237 Roundtrip, found 23 hours ago
$237
Roundtrip
found 23 hours ago
Select Southwest Airlines flight, departing Wed, Nov 12 from Amarillo to Chicago, returning Wed, Nov 19, priced at $237 found 23 hours ago
Southwest Airlines
Wed, Nov 12 - Wed, Nov 19
AMA
Amarillo
MDW
Chicago
$242 Roundtrip, found 23 hours ago
$242
Roundtrip
found 23 hours ago
Select Southwest Airlines flight, departing Wed, Nov 12 from Amarillo to Chicago, returning Wed, Nov 19, priced at $242 found 23 hours ago
Southwest Airlines
Sat, Aug 2 - Thu, Aug 7
AMA
Amarillo
MDW
Chicago
$247 Roundtrip, found 1 day ago
$247
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Aug 2 from Amarillo to Chicago, returning Thu, Aug 7, priced at $247 found 1 day ago
Southwest Airlines
Wed, Nov 12 - Wed, Nov 19
AMA
Amarillo
MDW
Chicago
$247 Roundtrip, found 23 hours ago
$247
Roundtrip
found 23 hours ago
Select Southwest Airlines flight, departing Wed, Nov 12 from Amarillo to Chicago, returning Wed, Nov 19, priced at $247 found 23 hours ago
Southwest Airlines
Sat, Aug 23 - Mon, Sep 8
AMA
Amarillo
MDW
Chicago
$252 Roundtrip, found 10 hours ago
$252
Roundtrip
found 10 hours ago
Select Southwest Airlines flight, departing Sat, Aug 23 from Amarillo to Chicago, returning Mon, Sep 8, priced at $252 found 10 hours ago
Southwest Airlines
Sat, Oct 4 - Wed, Oct 8
AMA
Amarillo
MDW
Chicago
$252 Roundtrip, found 3 days ago
$252
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sat, Oct 4 from Amarillo to Chicago, returning Wed, Oct 8, priced at $252 found 3 days ago
Southwest Airlines
Sat, Aug 23 - Mon, Sep 8
AMA
Amarillo
MDW
Chicago
$257 Roundtrip, found 10 hours ago
$257
Roundtrip
found 10 hours ago
Select Southwest Airlines flight, departing Sat, Aug 23 from Amarillo to Chicago, returning Mon, Sep 8, priced at $257 found 10 hours ago
Southwest Airlines
Sat, Aug 16 - Mon, Aug 18
AMA
Amarillo
MDW
Chicago
$267 Roundtrip, found 6 days ago
$267
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sat, Aug 16 from Amarillo to Chicago, returning Mon, Aug 18, priced at $267 found 6 days ago
Southwest Airlines
Sat, Aug 16 - Mon, Aug 18
AMA
Amarillo
MDW
Chicago
$267 Roundtrip, found 6 days ago
$267
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sat, Aug 16 from Amarillo to Chicago, returning Mon, Aug 18, priced at $267 found 6 days ago
Southwest Airlines
Wed, Nov 12 - Wed, Nov 19
AMA
Amarillo
MDW
Chicago
$272 Roundtrip, found 23 hours ago
$272
Roundtrip
found 23 hours ago
Select Southwest Airlines flight, departing Wed, Nov 12 from Amarillo to Chicago, returning Wed, Nov 19, priced at $272 found 23 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 $430
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $430
Flights from Amarillo (AMA) to Chicago (MDW)
Origin airport
Rick Husband Amarillo Intl.
Destination airport
Midway Intl.
Airlines serving
Southwest Airlines
Roundtrip price
$236
Distance
879 mi
Average flight time
4 hours 40 mins

Amarillo to Chicago Flights

The cheapest times to fly from Amarillo 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 Amarillo to Chicago are during the month of November. You can find some of the cheapest flights from Amarillo to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Amarillo to Chicago

Sunday is one of the best days to book for cheap flights from Amarillo 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 Amarillo 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 Amarillo to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $109 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 Amarillo 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 Amarillo 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 Rick Husband Amarillo Intl. Airport (AMA) to Midway Intl. Airport (MDW) cost?
Discover the latest flight deals from AMA to MDW by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from AMA to MDW?
The cheapest flights from AMA to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from AMA to MDW?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from AMA to MDW. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Rick Husband Amarillo Intl. Airport (AMA) to Midway Intl. Airport (MDW)?
Nonstop flights from Rick Husband Amarillo Intl. Airport (AMA) to Midway Intl. Airport (MDW) aren't available daily, so you'll have to take a flight with a layover. Explore your options with Expedia's filters. Enter your dates and select either "1 Stop" or "2+ Stops."
What day of the week has the most flights from AMA to MDW?
Usually you'll find the most flight options available on a Friday. Tuesdays are often the quietest.* But this can vary based on the airline, time of year 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 Rick Husband Amarillo Intl. Airport (AMA) to Midway Intl. Airport (MDW)?
Book a flight from Rick Husband Amarillo Intl. Airport (AMA) to Midway Intl. Airport (MDW) that leaves before 3 PM to reduce the risk of cancellations and delays. Departures after this hour are on average 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 Rick Husband Amarillo Intl. Airport (AMA) to Midway Intl. Airport (MDW) last-minute?
Waiting until right before your break to book a flight from AMA to MDW often results in higher prices. While you may find some last-minute deals, they aren't always guaranteed. Be flexible with your itinerary to boost your chances of snagging a bargain.
Is it cheaper to book an AMA to MDW flight and hotel package?
Compared with arranging flights and hotels separately, booking an AMA to MDW flight and hotel package with Expedia could lead to significant savings. Better yet, having everything in one easy place takes the hassle out of planning your trip. Simply pick your flights and select from our wide range of hotels, then customize your trip with extras like tours, activities and car rentals.
Can I cancel or change the date of my flight from Rick Husband Amarillo Intl. Airport (AMA) to Midway Intl. Airport (MDW)?
Typically, it's possible to reschedule or cancel your AMA to MDW flight. However, if it's been more than 24 hours since booking, additional fees may apply. Refer to your airline's policies in your itinerary to see what changes are possible and whether any costs are involved. You'll also find more details on our Customer Service portal.

Explore a world of travel with Expedia

*Available to One Key members.