$87 Cheap Flights from Amarillo (AMA) to Chicago (MDW)

View $87 flight on Wed, Nov 12, 2025Opens in a new window

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

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Cheap Flights from Amarillo to Chicago (AMA-MDW)

Prices were available within the past 7 days and start at $87 for one-way flights and $223 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Mon, Aug 25 - Tue, Aug 26
AMA
Amarillo
MDW
Chicago
$223 Roundtrip, just found
$223
Roundtrip
just found
Select Southwest Airlines flight, departing Mon, Aug 25 from Amarillo to Chicago, returning Tue, Aug 26, priced at $223 just found
Southwest Airlines
Mon, Aug 25 - Tue, Aug 26
AMA
Amarillo
MDW
Chicago
$225 Roundtrip, just found
$225
Roundtrip
just found
Select Southwest Airlines flight, departing Mon, Aug 25 from Amarillo to Chicago, returning Tue, Aug 26, priced at $225 just found
Southwest Airlines
Mon, Aug 25 - Tue, Aug 26
AMA
Amarillo
MDW
Chicago
$231 Roundtrip, just found
$231
Roundtrip
just found
Select Southwest Airlines flight, departing Mon, Aug 25 from Amarillo to Chicago, returning Tue, Aug 26, priced at $231 just found
Southwest Airlines
Wed, Sep 3 - Sat, Sep 6
AMA
Amarillo
MDW
Chicago
$237 Roundtrip, found 2 hours ago
$237
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Wed, Sep 3 from Amarillo to Chicago, returning Sat, Sep 6, priced at $237 found 2 hours ago
Southwest Airlines
Wed, Nov 12 - Mon, Nov 17
AMA
Amarillo
MDW
Chicago
$246 Roundtrip, found 1 day ago
$246
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Nov 12 from Amarillo to Chicago, returning Mon, Nov 17, priced at $246 found 1 day ago
Southwest Airlines
Wed, Aug 27 - Sun, Aug 31
AMA
Amarillo
MDW
Chicago
$251 Roundtrip, found 1 day ago
$251
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Aug 27 from Amarillo to Chicago, returning Sun, Aug 31, priced at $251 found 1 day ago
Southwest Airlines
Mon, Aug 25 - Tue, Aug 26
AMA
Amarillo
MDW
Chicago
$252 Roundtrip, just found
$252
Roundtrip
just found
Select Southwest Airlines flight, departing Mon, Aug 25 from Amarillo to Chicago, returning Tue, Aug 26, priced at $252 just found
Southwest Airlines
Sat, Oct 11 - Sat, Oct 25
AMA
Amarillo
MDW
Chicago
$253 Roundtrip, found 5 hours ago
$253
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Sat, Oct 11 from Amarillo to Chicago, returning Sat, Oct 25, priced at $253 found 5 hours ago
Southwest Airlines
Wed, Nov 12 - Mon, Nov 17
AMA
Amarillo
MDW
Chicago
$257 Roundtrip, found 1 day ago
$257
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Nov 12 from Amarillo to Chicago, returning Mon, Nov 17, priced at $257 found 1 day ago
Southwest Airlines
Tue, Aug 26 - Tue, Sep 2
AMA
Amarillo
MDW
Chicago
$259 Roundtrip, found 2 days ago
$259
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, Aug 26 from Amarillo to Chicago, returning Tue, Sep 2, priced at $259 found 2 days 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 $318
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $318
Flights from Amarillo (AMA) to Chicago (MDW)
Origin airport
Rick Husband Amarillo Intl.
Destination airport
Midway Intl.
Airlines serving
Southwest Airlines
Roundtrip price
$223
Distance
879 mi

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 August. 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 $87 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?
Get a cheap one-way flight from $87 or cheap return flight from $223 from Rick Husband Amarillo Intl. Airport (AMA) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Rick Husband Amarillo Intl. Airport (AMA) to Midway Intl. Airport (MDW)?
The cheapest month to fly from AMA to MDW is August, when demand is low. Off-peak months are often when airlines offer lower prices between these airports.
What is the cheapest airline that flies from Rick Husband Amarillo Intl. Airport (AMA) to Midway Intl. Airport (MDW)?
Use the filter tool on Expedia to compare different airlines and find the most affordable carrier that'll fly you from AMA to MDW. Then, sort your results by "Price (lowest to highest)" to snag a good 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.

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*Available to One Key members.