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Cheap flights from Chicago Midway Airport to Brainerd from $427

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Brainerd departing on 4/4. 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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Find the cheapest flights from Chicago Midway Airport to Brainerd

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
2:00 pm - 5:45 pmMDW-BRD
3h 45m1 stop
Delta Logo
6:20 pm - 8:54 amBRD-MDW
14h 34m1 stop
$427Delta
Find Deal
Sat, Apr 4 - Wed, Apr 8
Delta Logo
2:00 pm - 5:45 pmMDW-BRD
3h 45m1 stop
Delta Logo
6:20 pm - 1:08 pmBRD-MDW
18h 48m1 stop
$437Delta
Find Deal
Sat, Apr 4 - Wed, Apr 8
Delta Logo
2:00 pm - 5:45 pmMDW-BRD
3h 45m1 stop
Delta Logo
6:20 pm - 1:08 pmBRD-MDW
18h 48m1 stop
$447Delta
Find Deal
Sat, Apr 4 - Wed, Apr 8
Delta Logo
2:00 pm - 5:45 pmMDW-BRD
3h 45m1 stop
Delta Logo
6:20 pm - 12:35 pmBRD-MDW
18h 15m2 stops
$457Delta
Find Deal
Sat, Apr 4 - Wed, Apr 8
Delta Logo
9:30 am - 5:45 pmMDW-BRD
8h 15m2 stops
Delta Logo
6:20 pm - 12:35 pmBRD-MDW
18h 15m2 stops
$478Delta
Find Deal
Sat, Apr 4 - Wed, Apr 8
Delta Logo
9:30 am - 5:45 pmMDW-BRD
8h 15m2 stops
Delta Logo
6:20 pm - 12:35 pmBRD-MDW
18h 15m2 stops
$482Delta
Find Deal
Sat, Apr 4 - Wed, Apr 8
Delta Logo
9:30 am - 5:45 pmMDW-BRD
8h 15m2 stops
Delta Logo
6:20 pm - 12:35 pmBRD-MDW
18h 15m2 stops
$498Delta
Find Deal
Sat, Apr 4 - Wed, Apr 8
Delta Logo
1:48 pm - 5:42 pmMDW-BRD
3h 54m1 stop
Delta Logo
10:55 am - 6:25 pmBRD-MDW
7h 30m2 stops
$865Delta
Find Deal
Thu, Oct 23 - Mon, Oct 27
Delta Logo
9:35 am - 5:42 pmMDW-BRD
8h 07m2 stops
Delta Logo
10:55 am - 6:25 pmBRD-MDW
7h 30m2 stops
$870Delta
Find Deal
Thu, Oct 23 - Mon, Oct 27

Delta flights from Chicago Midway Airport to Brainerd

Our best Delta deals on Chicago Midway Airport to Brainerd flight tickets
Delta
Apr 4
MDW2:00 pmChicago Midway
3h 45m
1 stop
BRD5:45 pmBrainerd Crow Wing County
Apr 8
BRD6:20 pmBrainerd Crow Wing County
14h 34m
1 stop
MDW8:54 amChicago Midway
$427
Find similar
Delta
Apr 4
MDW2:00 pmChicago Midway
3h 45m
1 stop
BRD5:45 pmBrainerd Crow Wing County
Apr 8
BRD6:20 pmBrainerd Crow Wing County
18h 48m
1 stop
MDW1:08 pmChicago Midway
$437
Find similar
Delta
Apr 4
MDW2:00 pmChicago Midway
3h 45m
1 stop
BRD5:45 pmBrainerd Crow Wing County
Apr 8
BRD6:20 pmBrainerd Crow Wing County
18h 48m
1 stop
MDW1:08 pmChicago Midway
$447
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Brainerd 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 October 9, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Brainerd that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoBrainerd

MDW - BRD

MDWBRD

Chicago Midway

Sat 4/4

2:00 pm-5:45 pm

1 stop3h 45m

Brainerd Crow Wing County

Wed 4/8

6:20 pm-8:54 am

1 stop14h 34m

$427

ChicagoBrainerd

MDW - BRD

MDWBRD

Chicago Midway

Sat 4/4

2:00 pm-5:45 pm

1 stop3h 45m

Brainerd Crow Wing County

Wed 4/8

6:20 pm-1:08 pm

1 stop18h 48m

$437

ChicagoBrainerd

MDW - BRD

MDWBRD

Chicago Midway

Sat 4/4

2:00 pm-5:45 pm

1 stop3h 45m

Brainerd Crow Wing County

Wed 4/8

6:20 pm-1:08 pm

1 stop18h 48m

$447

ChicagoBrainerd

MDW - BRD

MDWBRD

Chicago Midway

Sat 4/4

2:00 pm-5:45 pm

1 stop3h 45m

Brainerd Crow Wing County

Wed 4/8

6:20 pm-12:35 pm

2 stops18h 15m

$457

ChicagoBrainerd

MDW - BRD

MDWBRD

Chicago Midway

Sat 4/4

9:30 am-5:45 pm

2 stops8h 15m

Brainerd Crow Wing County

Wed 4/8

6:20 pm-12:35 pm

2 stops18h 15m

$478

ChicagoBrainerd

MDW - BRD

MDWBRD

Chicago Midway

Sat 4/4

9:30 am-5:45 pm

2 stops8h 15m

Brainerd Crow Wing County

Wed 4/8

6:20 pm-12:35 pm

2 stops18h 15m

$482

ChicagoBrainerd

MDW - BRD

MDWBRD

Chicago Midway

Sat 4/4

9:30 am-5:45 pm

2 stops8h 15m

Brainerd Crow Wing County

Wed 4/8

6:20 pm-12:35 pm

2 stops18h 15m

$498

ChicagoBrainerd

MDW - BRD

MDWBRD

Chicago Midway

Thu 10/23

1:48 pm-5:42 pm

1 stop3h 54m

Brainerd Crow Wing County

Mon 10/27

10:55 am-6:25 pm

2 stops7h 30m

$865

ChicagoBrainerd

MDW - BRD

MDWBRD

Chicago Midway

Thu 10/23

9:35 am-5:42 pm

2 stops8h 07m

Brainerd Crow Wing County

Mon 10/27

10:55 am-6:25 pm

2 stops7h 30m

$870

ChicagoBrainerd

MDW - BRD

MDWBRD

Chicago Midway

Fri 10/17

1:48 pm-5:42 pm

1 stop3h 54m

$656

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

See travel insights to Brainerd from

How to get the cheapest flight ticket from Chicago Midway Airport to Brainerd

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 cheapest day to depart on your flight to Brainerd?

Our data shows that Tuesday is the least expensive day to fly to Brainerd. Tickets to fly out on this day can be as low as $463. The most expensive day to fly to Brainerd is Friday, with ticket prices averaging around $553.

When to book flights from Chicago Midway Airport to Brainerd

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

Cheap Chicago Midway Airport to Brainerd (MDW to BRD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Brainerd

Direct flights

None
There are no direct flights from Chicago Midway Airport to Brainerd. There are no popular flight routes from Chicago Midway Airport to Brainerd.
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  • How far is Chicago Midway to Brainerd Crow Wing County by plane?

    The distance between Chicago Midway and Brainerd Crow Wing County is about 449.3 mi. Flights usually cover this in 3h 45m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Chicago Midway Airport to Brainerd Crow Wing County Airport?

    Prices for flights from Chicago Midway Airport to Brainerd Crow Wing County Airport were last updated today.

  • How old do you have to be to fly from Chicago Midway Airport to Brainerd Crow Wing County Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Brainerd Crow Wing County Airport.

  • What documentation or ID do you need to fly to Brainerd Crow Wing County Airport?

    The required travel and health documents for your Brainerd Crow Wing County Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Brainerd Crow Wing County Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Traveling to a place near Brainerd?

Book flights to Brainerd if you plan to visit one of these locations
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Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Brainerd from Chicago.

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

Yes. momondo enables you to select and highlight flights to Brainerd from Chicago with this policy.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Brainerd.

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

Yes momondo offers price alerts on flights to Brainerd from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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