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Cheap flights from Montgomery, Alabama to Chicago from $294

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Montgomery, Alabama to Chicago departing on 7/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Montgomery, Alabama to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:28 pm - 11:58 pm
MGM
-
ORD
5h 30m
1 stop
Delta Logo
5:28 am - 9:15 am
ORD
-
MGM
3h 47m
1 stop
$334Delta
Mon, Aug 3 - Sat, Aug 8
Delta Logo
6:27 pm - 10:17 pm
MGM
-
MDW
3h 50m
1 stop
Delta Logo
12:50 pm - 5:47 pm
MDW
-
MGM
4h 57m
1 stop
$334Delta
Fri, Jun 12 - Fri, Jun 19
Delta Logo
6:28 pm - 9:27 am
MGM
-
ORD
14h 59m
2 stops
Delta Logo
5:28 am - 9:15 am
ORD
-
MGM
3h 47m
1 stop
$369Delta
Mon, Aug 3 - Wed, Aug 12
Delta Logo
6:27 pm - 11:59 pm
MGM
-
ORD
5h 32m
1 stop
Delta Logo
6:22 pm - 11:12 pm
ORD
-
MGM
4h 50m
1 stop
$375Delta
Tue, Jun 9 - Tue, Jun 23
Delta Logo
9:53 am - 4:16 pm
MGM
-
MDW
6h 23m
1 stop
Delta Logo
12:50 pm - 5:47 pm
MDW
-
MGM
4h 57m
1 stop
$375Delta
Tue, Jun 9 - Fri, Jun 19
Delta Logo
6:27 pm - 8:05 am
MGM
-
ORD
13h 38m
2 stops
Delta Logo
6:22 pm - 11:12 pm
ORD
-
MGM
4h 50m
1 stop
$384Delta
Tue, Jun 9 - Tue, Jun 23
Delta Logo
6:27 pm - 9:14 am
MGM
-
MDW
14h 47m
2 stops
Delta Logo
5:11 pm - 11:12 pm
MDW
-
MGM
6h 01m
1 stop
$384Delta
Tue, Jun 9 - Tue, Jun 23
Delta Logo
6:27 pm - 11:59 pm
MGM
-
ORD
5h 32m
1 stop
Delta Logo
5:30 am - 2:46 pm
ORD
-
MGM
9h 16m
1 stop
$396Delta
Sun, Jun 14 - Sat, Jun 20
American Airlines Logo
3:20 pm - 9:33 pm
MGM
-
ORD
6h 13m
1 stop
American Airlines Logo
5:59 am - 11:59 am
ORD
-
MGM
6h 00m
1 stop
$399American Airlines
Thu, Jun 25 - Tue, Jun 30
American Airlines Logo
3:20 pm - 9:33 pm
MGM
-
ORD
6h 13m
1 stop
American Airlines Logo
8:00 am - 2:55 pm
ORD
-
MGM
6h 55m
2 stops
$405American Airlines
Wed, Jun 17 - Sat, Jun 20

United Airlines flights from Montgomery, Alabama to Chicago

Our best United Airlines deals on Montgomery, Alabama to Chicago flight tickets
United Airlines
Jun 15
MGM1:00 pmMontgomery Dannelly Field
18h 39m
2 stops
ORD7:39 amChicago O'Hare Intl
Jun 21
ORD6:30 amChicago O'Hare Intl
5h 40m
1 stop
MGM12:10 pmMontgomery Dannelly Field
$569
United Airlines
Jun 3
MGM1:00 pmMontgomery Dannelly Field
17h 28m
2 stops
ORD6:28 amChicago O'Hare Intl
Jun 8
ORD7:59 pmChicago O'Hare Intl
20h 17m
2 stops
MGM4:16 pmMontgomery Dannelly Field
$572
United Airlines
May 28
MGM4:51 pmMontgomery Dannelly Field
7h 54m
1 stop
ORD12:45 amChicago O'Hare Intl
Jun 1
ORD6:30 amChicago O'Hare Intl
5h 40m
1 stop
MGM12:10 pmMontgomery Dannelly Field
$574

American Airlines flights from Montgomery, Alabama to Chicago

Our best American Airlines deals on Montgomery, Alabama to Chicago flight tickets
American Airlines
Jun 25
MGM3:20 pmMontgomery Dannelly Field
6h 13m
1 stop
ORD9:33 pmChicago O'Hare Intl
Jun 30
ORD5:59 amChicago O'Hare Intl
6h 00m
1 stop
MGM11:59 amMontgomery Dannelly Field
$399
American Airlines
Jun 17
MGM3:20 pmMontgomery Dannelly Field
6h 13m
1 stop
ORD9:33 pmChicago O'Hare Intl
Jun 20
ORD8:00 amChicago O'Hare Intl
6h 55m
2 stops
MGM2:55 pmMontgomery Dannelly Field
$405
American Airlines
Jun 13
MGM6:01 pmMontgomery Dannelly Field
6h 38m
1 stop
ORD12:39 amChicago O'Hare Intl
Jun 17
ORD8:00 amChicago O'Hare Intl
6h 55m
1 stop
MGM2:55 pmMontgomery Dannelly Field
$414

momondo Fare Finder

 
Customize your flight search to find flights from Montgomery, Alabama to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated May 17, 2026.
Use the filters below to find and compare flights from Montgomery, Alabama to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MontgomeryChicago

MGM - ORD

MGMORD

Montgomery Dannelly Field

Mon 8/3

6:28 pm-11:58 pm

1 stop5h 30m

Chicago O'Hare Intl

Sat 8/8

5:28 am-9:15 am

1 stop3h 47m

$334
Quickest round-trip

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Fri 6/12

6:27 pm-10:17 pm

1 stop3h 50m

Chicago Midway

Fri 6/19

12:50 pm-5:47 pm

1 stop4h 57m

$334

MontgomeryChicago

MGM - ORD

MGMORD

Montgomery Dannelly Field

Mon 8/3

6:28 pm-9:27 am

2 stops14h 59m

Chicago O'Hare Intl

Wed 8/12

5:28 am-9:15 am

1 stop3h 47m

$369

MontgomeryChicago

MGM - ORD

MGMORD

Montgomery Dannelly Field

Tue 6/9

6:27 pm-11:59 pm

1 stop5h 32m

Chicago O'Hare Intl

Tue 6/23

6:22 pm-11:12 pm

1 stop4h 50m

$375

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Tue 6/9

9:53 am-4:16 pm

1 stop6h 23m

Chicago Midway

Fri 6/19

12:50 pm-5:47 pm

1 stop4h 57m

$375

MontgomeryChicago

MGM - ORD

MGMORD

Montgomery Dannelly Field

Tue 6/9

6:27 pm-8:05 am

2 stops13h 38m

Chicago O'Hare Intl

Tue 6/23

6:22 pm-11:12 pm

1 stop4h 50m

$384

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Tue 6/9

6:27 pm-9:14 am

2 stops14h 47m

Chicago Midway

Tue 6/23

5:11 pm-11:12 pm

1 stop6h 01m

$384

MontgomeryChicago

MGM - ORD

MGMORD

Montgomery Dannelly Field

Sun 6/14

6:27 pm-11:59 pm

1 stop5h 32m

Chicago O'Hare Intl

Sat 6/20

5:30 am-2:46 pm

1 stop9h 16m

$396

MontgomeryChicago

MGM - ORD

MGMORD

Montgomery Dannelly Field

Thu 6/25

3:20 pm-9:33 pm

1 stop6h 13m

Chicago O'Hare Intl

Tue 6/30

5:59 am-11:59 am

1 stop6h 00m

$399

MontgomeryChicago

MGM - ORD

MGMORD

Montgomery Dannelly Field

Wed 6/17

3:20 pm-9:33 pm

1 stop6h 13m

Chicago O'Hare Intl

Sat 6/20

8:00 am-2:55 pm

2 stops6h 55m

$405

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Montgomery, Alabama to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Montgomery, Alabama and Chicago?

What is the cheapest month to fly to Chicago?

The month of October is, on average, the cheapest month to fly to Chicago from Montgomery, Alabama, with most prices found around $78. If you’re not able to fly to Chicago in October, then September is your next best option. Flight prices from Montgomery, Alabama to Chicago during September average around $116.

Can stopping save me money on Montgomery, Alabama to Chicago flights?

You could potentially save up to 54% on your flight if you consider stops on a Montgomery, Alabama to Chicago flight.

When to book flights from Montgomery, Alabama to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Montgomery, Alabama to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Montgomery, Alabama to Chicago (MGM to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Montgomery, Alabama to Chicago

Fastest flight time

3h 47m

Direct flights

None
The fastest flight from Montgomery, Alabama to Chicago takes 3h 47m
There are no direct flights from Montgomery, Alabama to Chicago. There are no popular flight routes from Montgomery, Alabama to Chicago.
Search flight deals

Frequently asked questions about flying from Montgomery, Alabama to Chicago

  • How far is Montgomery Dannelly Field to Chicago by plane?

    A flight from Montgomery Dannelly Field to Chicago will travel around 660.6 mi. Flights usually cover this in 3h 47m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Montgomery Dannelly Field Airport to Chicago?

    Prices for flights from Montgomery Dannelly Field Airport to Chicago are updated daily.

  • How many operators does momondo search for flights from Montgomery Dannelly Field Airport to Chicago?

  • How old do you have to be to fly from Montgomery Dannelly Field Airport to Chicago?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Montgomery Dannelly Field Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Montgomery, Alabama to Chicago?

Best airlines flying from Montgomery, Alabama to Chicago

Compare and see reviews for airlines that fly from Montgomery, Alabama to Chicago with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $234Free CancellationRating
7.9
8,453 reviews
Search Delta flights
American AirlinesPriceFrom $328Free CancellationRating
7.1
11,654 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Montgomery to Chicago?

Finding the right flight to Chicago from Montgomery is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Montgomery to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Montgomery to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from Montgomery to Chicago?

momondo helps you find the best flight between Montgomery and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Montgomery to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Montgomery to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport