$179 Cheap Flights from Amarillo (AMA) to Chicago (MDW)

Book with confidence

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 January. 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 2026. You can also book with separate airlines for your outbound and return journeys, from $179 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 Amarillo, TX (AMA-Rick Husband Amarillo Intl.) to Chicago, IL (MDW-Midway Intl.) cost?

You can find cheap one-way flights from $179 and cheap return flights $381 Amarillo, TX (AMA-Rick Husband Amarillo Intl.) to Chicago, IL (MDW-Midway Intl.) with Expedia. One-way flights typically cost between $229 and $573, and return flights often range between $568 and $1517. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Amarillo, TX (AMA-Rick Husband Amarillo Intl.) to Chicago, IL (MDW-Midway Intl.) ticket fares go up or down.

*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.

What is the cheapest month to fly from Amarillo, TX (AMA-Rick Husband Amarillo Intl.) to Chicago, IL (MDW-Midway Intl.)?

The cheapest month to fly from AMA to MDW is January when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route.

Which airlines fly direct from Amarillo, TX (AMA-Rick Husband Amarillo Intl.) to Chicago, IL (MDW-Midway Intl.)?

Enter AMA to MDW and your travel dates, then apply the 'Nonstop' filter to see only direct flights.

How do I find cheap flights from Amarillo, TX (AMA-Rick Husband Amarillo Intl.) to Chicago, IL (MDW-Midway Intl.)?

To find a cheap flight from Amarillo, TX (AMA-Rick Husband Amarillo Intl.) to Chicago, IL (MDW-Midway Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.

What is the best time to fly from Amarillo, TX (AMA-Rick Husband Amarillo Intl.) to Chicago, IL (MDW-Midway Intl.)?

The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.

What is the earliest flight from Amarillo, TX (AMA-Rick Husband Amarillo Intl.) to Chicago, IL (MDW-Midway Intl.)?

The earliest flight from Rick Husband Amarillo International Airport (AMA) to Midway International Airport (MDW) typically departs at around 5:20 AM. This seasonal service is operated by Southwest Airlines, allowing you to start your day early and maximize your time in Chicago. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.

What are the most popular departure times for flights from Amarillo, TX (AMA-Rick Husband Amarillo Intl.) to Chicago, IL (MDW-Midway Intl.)?

The most popular departure times for flights from Amarillo, TX (AMA-Rick Husband Amarillo Intl.) to Chicago, IL (MDW-Midway Intl.) are in the late morning, from 9am to noon. About 32% of passengers prefer this time window. Many major carriers, including Southwest Airlines, operate flights during this period. This timing works well for travelers looking to maximize their day in Chicago upon arrival.

How long does it take to fly from Amarillo, TX (AMA-Rick Husband Amarillo Intl.) to Chicago, IL (MDW-Midway Intl.)?

Flying from AMA to MDW with a connection usually takes about 6 hours 50 minutes, traveling roughly 879 miles. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.

Can you fly business or first class from Amarillo, TX (AMA-Rick Husband Amarillo Intl.) to Chicago, IL (MDW-Midway Intl.)?

Select the "Business class" and "First class" filters when looking for AMA to MDW flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.

How do I earn miles on a Amarillo, TX (AMA-Rick Husband Amarillo Intl.) to Chicago, IL (MDW-Midway Intl.) flight with Expedia?

It's easy to earn miles on a Amarillo, TX (AMA-Rick Husband Amarillo Intl.) to Chicago, IL (MDW-Midway Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

What airports do you fly into for Chicago from Rick Husband Amarillo Intl. (AMA)?

When traveling from Rick Husband Amarillo Intl. (AMA) to Chicago, you can fly into O'Hare Intl. (ORD) and Midway Intl. (MDW). Some flights may connect through major hubs like George Bush Intercontinental (IAH), Dallas-Fort Worth Intl. (DFW), Denver Intl. (DEN) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.

Is it cheaper to buy a plane ticket from Amarillo, TX (AMA-Rick Husband Amarillo Intl.) to Chicago, IL (MDW-Midway Intl.) at the last minute?

Typically, booking a last minute flight from Amarillo, TX (AMA-Rick Husband Amarillo Intl.) to Chicago, IL (MDW-Midway Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.

Is it cheaper to book a Amarillo, TX (AMA-Rick Husband Amarillo Intl.) to Chicago, IL (MDW-Midway Intl.) flight and hotel package?

Securing a Amarillo, TX (AMA-Rick Husband Amarillo Intl.) to Chicago, IL (MDW-Midway Intl.) Chicago Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.

Can I cancel or change the date of my flight from Amarillo, TX (AMA-Rick Husband Amarillo Intl.) to Chicago, IL (MDW-Midway Intl.)?

If you booked your Amarillo, TX (AMA-Rick Husband Amarillo Intl.) to Chicago, IL (MDW-Midway Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.