CHI - MGM

$189 Find Cheap Flights from Chicago to Montgomery - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Montgomery departing on 9/5. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$326
Delta
Fri 9/11Fri 9/18
MDW - MGM • 1 stop
Cheapest one-way
$189
American Airlines
Sat 9/5
ORD - MGM • 1 stop
Top airlines
Cheapest • from $326 (round-trip)
Best reviews • 7.8 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Chicago and Montgomery. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $297 (round-trip)
Shortest trip • 4h 10m (one-way)
Insights
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Flight Deals

Cheap Flights from Chicago to Montgomery (CHI-MGM)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Montgomery that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Montgomery

Fri, Sep 11 - Fri, Sep 18
Delta Logo
6:05 am - 12:30 pmMDW  Chicago Midway-MGM Montgomery Dannelly Field
6h 25m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:28 pm - 10:44 pmMGM  Montgomery Dannelly Field-MDW Chicago Midway
4h 16m1 stop Atlanta Hartsfield-Jackson
$326Delta
Mon, Sep 14 - Mon, Sep 21
Delta Logo
6:05 am - 11:48 amMDW  Chicago Midway-MGM Montgomery Dannelly Field
5h 43m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:28 pm - 10:44 pmMGM  Montgomery Dannelly Field-MDW Chicago Midway
4h 16m1 stop Atlanta Hartsfield-Jackson
$326Delta
Thu, Sep 24 - Sat, Sep 26
American Airlines Logo
1:19 pm - 8:53 pmORD  Chicago O'Hare Intl-MGM Montgomery Dannelly Field
7h 34m1 stop Charlotte Douglas
American Airlines Logo
6:10 pm - 12:14 amMGM  Montgomery Dannelly Field-ORD Chicago O'Hare Intl
6h 04m1 stop Dallas/Fort Worth
$326American Airlines
Mon, Aug 24 - Mon, Aug 31
American Airlines Logo
4:53 pm - 10:32 pmORD  Chicago O'Hare Intl-MGM Montgomery Dannelly Field
5h 39m1 stop Charlotte Douglas
American Airlines Logo
6:39 am - 12:15 pmMGM  Montgomery Dannelly Field-ORD Chicago O'Hare Intl
5h 36m1 stop Charlotte Douglas
$326American Airlines
Fri, Oct 9 - Tue, Oct 13
Delta Logo
10:59 am - 5:43 pmMDW  Chicago Midway-MGM Montgomery Dannelly Field
6h 44m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:23 pm - 10:33 pmMGM  Montgomery Dannelly Field-MDW Chicago Midway
4h 10m1 stop Atlanta Hartsfield-Jackson
$326Delta
Fri, Oct 9 - Sun, Oct 11
Delta Logo
10:59 am - 5:43 pmMDW  Chicago Midway-MGM Montgomery Dannelly Field
6h 44m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 10:03 amMGM  Montgomery Dannelly Field-MDW Chicago Midway
4h 03m1 stop Atlanta Hartsfield-Jackson
$326Delta
Tue, Aug 25 - Wed, Sep 9
American Airlines Logo
3:54 pm - 10:31 pmORD  Chicago O'Hare Intl-MGM Montgomery Dannelly Field
6h 37m1 stop Dallas/Fort Worth
American Airlines Logo
12:31 pm - 7:36 pmMGM  Montgomery Dannelly Field-ORD Chicago O'Hare Intl
7h 05m1 stop Dallas/Fort Worth
$326American Airlines
Tue, Sep 29 - Thu, Oct 1
United Airlines Logo
10:32 am - 4:17 pmORD  Chicago O'Hare Intl-MGM Montgomery Dannelly Field
5h 45m1 stop Houston George Bush Intcntl
United Airlines Logo
1:17 pm - 9:42 pmMGM  Montgomery Dannelly Field-ORD Chicago O'Hare Intl
8h 25m1 stop Houston George Bush Intcntl
$536United Airlines
Tue, Aug 25 - Thu, Aug 27
United Airlines Logo
10:40 am - 4:17 pmORD  Chicago O'Hare Intl-MGM Montgomery Dannelly Field
5h 37m1 stop Houston George Bush Intcntl
United Airlines Logo
4:53 pm - 11:26 pmMGM  Montgomery Dannelly Field-ORD Chicago O'Hare Intl
6h 33m1 stop Houston George Bush Intcntl
$536United Airlines
Wed, Oct 7 - Thu, Oct 8
United Airlines Logo
8:45 am - 4:17 pmORD  Chicago O'Hare Intl-MGM Montgomery Dannelly Field
7h 32m1 stop Houston George Bush Intcntl
United Airlines Logo
4:53 pm - 12:23 amMGM  Montgomery Dannelly Field-ORD Chicago O'Hare Intl
7h 30m1 stop Houston George Bush Intcntl
$558United Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Montgomery flights

Get data-powered insights and trends into flights from Chicago to Montgomery to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Chicago to Montgomery?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Montgomery, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Montgomery is December, where tickets cost $0 (return) on average. On the other hand, the most expensive months are March and June, where the average cost of round-trip tickets is $1,312 and $1,042 respectively.

Good to know

Cheapest flight

$189
Flight from Chicago Midway Airport to Montgomery

When to book flights from Chicago to Montgomery

Are your dates flexible? Find out the best times to travel from Chicago to Montgomery based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Chicago to Montgomery

  • What is the cheapest flight from Chicago to Montgomery?

    In the last 5 days, the lowest price for a flight from Chicago to Montgomery was $189 for a one-way ticket and $326 for a round-trip.

  • Do I need a passport to fly between Chicago and Montgomery?

    A passport is not required to fly from Chicago to Montgomery.

  • Which airports will I be using when flying from Chicago to Montgomery?

    On your way to Montgomery, you’ll fly out from one of these Chicago airports: Chicago Midway or Chicago O'Hare Intl. You’ll be landing at Montgomery Dannelly Field.

  • Which aircraft models fly most regularly from Chicago to Montgomery?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago to Montgomery?

    oneworld, and SkyTeam are the airline alliances operating flights between Chicago and Montgomery, with oneworld being the most commonly used for this route.

  • How does KAYAK find such low prices on flights from Chicago to Montgomery?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Montgomery.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Montgomery?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Montgomery from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Montgomery?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Montgomery with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Montgomery?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Montgomery from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Chicago to Montgomery

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Montgomery. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Montgomery? 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.
7.8
DeltaOverall score based on 8490 reviews
8.5Crew
7.8Comfort
7.8Entertainment
7.2Food
8.1Boarding
Airline reviews

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.

2.0 MediocreJean, Jun 2026
Read more Delta reviews

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.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Stop changing gates. Stop cancelling flights Stop moving my seat.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

This was one of the worst flights I’ve been on in years. I upgraded to comfort and had such an uncomfortable experience. The person next to me was oversized - which I understand - however, they took up their space and mine. I could only use about 50% of my seat space to not be physically touching this person the entire flight and there was no spatial awareness. I also could not use the seat outlet because their body was obstructing it. It was very inconvenient. Their body kept touching me repeatedly during the flight and I felt very uncomfortable. To pay more for an upgraded space and then not even being able to use it was highly disappointing.

It was very cold because the air conditioner was on high power, and my son got sick.

The boarding process was terrible especially with an indirect flight Chicago to Seattle to San Diego was terrible talking about we overbooked a flight idk if I’d take this airline ever again we got off our flight from Chicago to Seattle and we traveled for business and they told us our connecting flight was over booked and their was no seats asking people to take a delayed next flight and they don’t tell anyone coughing to wear masks seats 30A-B were terrible during the flight no one wants to sit next to people coughing all around I don’t want to be sick traveling for work or get sick anytime it’s very upsetting the staff doesn’t take this stuff serious to tell them to wear masks when they see people coughing and sneezing

Everything you need to know for your flight from Chicago to Montgomery

Information on your arrival and departure airports