$135 Find Cheap Flights from Chicago Midway Airport to Alabama - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 26% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Midway to Alabama

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Sort by: Cheapest
Birmingham
1h 40mNonstop
from $269per person
Huntsville
3h 39m2 stops
from $276per person
Mobile
4h 20m2 stops
from $347per person
Montgomery
4h 42m2 stops
from $414per person
Explore the map
Booking Insights

Price, demand and travel trends for Chicago Midway Airport to Alabama flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

What are the cheapest fares from Chicago Midway Airport to Alabama recently?

The cheapest fares from Chicago Midway Airport to Alabama on KAYAK in the last week were to Birmingham (BHM) from $269 round-trip and to Huntsville (HSV) from $276 round-trip.

How do fares into airports in Alabama compare?

According to KAYAK data from the last 12 months, the cheapest airports to fly into Alabama from Chicago Midway Airport are:

• Huntsville (HSV) (avg. price $348)
• Birmingham (BHM) (avg. price $399)
• Montgomery Dannelly Field (MGM) (avg. price $411)

What's the cheapest month to fly from Chicago Midway Airport to Alabama?

September is typically the cheapest month to fly from Chicago Midway Airport to Alabama, with round-trip fares averaging $375. April and January are usually the most expensive, averaging $913 and $551, respectively.

How do fares from Chicago Midway Airport to Alabama vary by day of the week?

On average, Tuesday is the cheapest day to fly from Chicago Midway Airport to Alabama and Monday is the most expensive. Looking at the past 12 months of KAYAK data, it's 17% more expensive to fly on a Monday compared to Tuesday.

What's the best time of day to fly from Chicago Midway Airport to Alabama?

It's cheapest to fly to Alabama at night with average prices of $387. The evening is the most expensive time to fly, with average prices of $488.

Key details for Chicago Midway Airport to Alabama flights

Low season

February

Cheapest flight

$135
Beat the crowds with an average 41% drop in travelers.
The most popular month to fly with an average 59% increase in travelers.
One-way flight from Chicago Midway Airport to Birmingham

Your Chicago Midway Airport to Alabama flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Is now a good time to book a flight from Chicago Midway Airport to Alabama?

    Yes. Fares from Chicago Midway Airport to Alabama are low right now. As a rule of thumb, a round-trip under $355 (cheaper than most fares this year) is a good deal, so if you spot one at or below that, it's a good time to book.

  • How much should I budget for a flight from Chicago Midway Airport to Alabama?

    Over the past 12 months, round-trip fares from Chicago Midway Airport to Alabama have typically cost between $355 and $543.

  • What are the main airports serving Alabama?

    Alabama has 13 airports. 84% of KAYAK users choose Birmingham (BHM) as their arrival airport.

  • Which airlines fly nonstop from Chicago Midway Airport to Alabama?

    Based on the flight schedule for the next 3 months, just one airline regularly flies nonstop from Chicago Midway Airport to Alabama: Southwest.

  • Which destinations in Alabama can I fly nonstop from Chicago Midway Airport?

    Based on the flight schedule for the next 3 months, you can fly nonstop from Chicago Midway Airport to just one destination in Alabama: Birmingham.

  • Is it cheaper to fly with a layover from Chicago Midway Airport to Alabama?

    Yes, nonstop flights from Chicago Midway Airport to Alabama average $389 over the past 12 months. Flights with a layover can cost less, cheapest when connecting through Detroit Metropolitan Wayne County (DTW), with average fares of $348.

  • How long is a flight from Chicago Midway Airport to Alabama?

    Nonstop flights from Chicago Midway Airport to Alabama take 1h 48m on average. All flights fly into Birmingham (BHM).

  • Which cabin classes are available from Chicago Midway Airport to Alabama?

    On flights from Chicago Midway Airport to Alabama you can only book Economy Class.

  • What are some popular landmarks around Alabama?

    Alabama is home to many popular sights. KAYAK travelers' favorites include:

    • UAB Hospital Jefferson Tower
    • Alys Robinson Stephens Performing Arts Center

  • What are the earliest and latest flights from Chicago Midway Airport to Alabama?

    The earliest nonstop flight from Chicago Midway Airport to Alabama departs at 7:40 am and the latest leaves at 10:50 pm. Nonstop flights take about 1h 48m.

Your guide to booking Chicago Midway Airport to Alabama flights

Get tips on when to book, when to fly and what to know before your trip.
  • Flexible with your dates? Fly in September to save some money. It's typically the cheapest month on this route, while flights in April will cost you the most.
  • Fly out on a Tuesday to get the cheapest fares. Avoid Monday flights, which are about 17% more expensive.
  • If you're watching your budget, fly into Huntsville (HSV) which has the lowest average airfare in the region. Just remember to budget for any onward travel by bus, car or domestic flight.
  • Start your trip in Gulf Shores, the most popular destination in Alabama. From there, it's easy to continue on to other popular spots such as Orange Beach, Birmingham and Mobile.
  • Time or money? If speed matters most, fly from Chicago Midway Airport to Birmingham (BHM). If you're after the lowest fares, Huntsville (HSV) is usually your best bet.

Reviews of the top airlines flying from Midway to Alabama

 
Need help choosing which airline to fly with from Midway to Alabama? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4220 reviews
7.5Entertainment
8.1Boarding
8.6Crew
7.0Food
8.0Comfort
Airline reviews

Multiple delays due to weather in Chicago, but the crew did their best to get flights rescheduled and on to their destination. I felt like the crews handled a frustrating situation very well, kudos to them! I was very glad to not have a cancelled flight.

8.0 ExcellentEmmalee, Oct 2026
Read more Southwest reviews

Multiple delays due to weather in Chicago, but the crew did their best to get flights rescheduled and on to their destination. I felt like the crews handled a frustrating situation very well, kudos to them! I was very glad to not have a cancelled flight.

Southwest’s point to point system caused a 2 hour delay due to the crew being late from their inbound flight. Also, the WiFi and entertainment didn’t work on the plane.

A) Checked my luggage at the gate but never got to pre board B) if we are helping with checking our carryon and waiting 40 minutes for it we should have some privileges c) luggage took 40-45 minutes to come.. d) I asked for another snack and was told the plane is full.. seriously a small snack

I like the staff members they were super nice and helpful very sweet people :)

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

No beverage/snack service without any explanation or reason. Late boarding and delayed flight.

The cabin and bathroom experience was poor as the cabin and bathroom were dirty and showed signs of an older plane that had not been updated for Customer’s, comfort and health. There was gum on my seat when I arrived and dirt spots around the fan and light controls. The flight was almost entirely full, so there was no way I could be moved from my seat. Th bathroom had the peeling paint.

I'm 6' 2" and even in economy plenty of leg room

Horrible experience. Delta delayed the flight to 11pm which happens. Apparently the pilots were there but we were waiting for flight attendants to arrive from Detroit and they were delayed. They could have made arrangements but that’s fine. What was truly horrible was that at 10:50pm the pilot comes out and says the flight will be cancelled but hasn’t been cancelled yet in the system. It’s being cancelled because the pilots have timed out. As soon as that plane got delayed past 10:50pm delta knew it couldn’t fly. Yet they made us wait around for hours. When the flight finally got cancelled all the area hotels were booked and flights for the next day were unavailable until midday. All I wanted was to spend one day with my family before needing to fly abroad on another delta flight. That will be my last flight with them. I’ll take my 800k miles flown and annual spend to an airline that isn’t so thoughtless.

THI IS THE 3RD CONSECUTIVE FLIGHT FROM ORD TO MSP THAT HAS BEEN DELAYED 2+ HOURS. CRAZY

The plane was a rather tired 737-800, with old style small luggage bins. Poor air flow. USB charger in the infotainment system was not functioning. The flight was 2 hours late due to crew rest requirements (not their fault). On arrival in Seattle, waited on the tarmac for 30 minutes with very few updates from the crew.

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

Very easy to use and convenient, you can perform any action within the same portal

Okay considering we had weather delays which the Pilot notified us of immediately!

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

More options for your flight from Midway to Alabama

Complete your trip to Alabama with a hotel stay or car rental