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Cheap flights from Chicago Midway Airport to Brainerd from $258

This is the cheapest one-way 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 7/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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
1:49 pm - 6:56 pm
MDW
-
BRD
5h 07m
1 stop
Delta Logo
6:45 am - 12:38 pm
BRD
-
MDW
5h 53m
2 stops
$442Delta
Sat, Jul 4 - Wed, Jul 8
Delta Logo
1:26 pm - 6:56 pm
MDW
-
BRD
5h 30m
2 stops
Delta Logo
6:45 am - 12:38 pm
BRD
-
MDW
5h 53m
2 stops
$447Delta
Sat, Jul 4 - Wed, Jul 8
Delta Logo
1:49 pm - 6:56 pm
MDW
-
BRD
5h 07m
1 stop
Delta Logo
6:45 am - 1:09 pm
BRD
-
MDW
6h 24m
1 stop
$526Delta
Sat, Jul 4 - Wed, Jul 8
Delta Logo
1:49 pm - 6:55 pm
MDW
-
BRD
5h 06m
1 stop
Delta Logo
6:45 am - 1:09 pm
BRD
-
MDW
6h 24m
1 stop
$624Delta
Mon, Jul 20 - Mon, Jul 27
Delta Logo
1:49 pm - 6:56 pm
MDW
-
BRD
5h 07m
1 stop
Delta Logo
6:45 am - 1:09 pm
BRD
-
MDW
6h 24m
1 stop
$1,025Delta
Sun, Jul 5 - Sat, Jul 11
Delta Logo
1:49 pm - 6:55 pm
MDW
-
BRD
5h 06m
1 stop
Delta Logo
10:55 am - 6:25 pm
BRD
-
MDW
7h 30m
2 stops
$1,029Delta
Mon, Jul 20 - Mon, Jul 27
Delta Logo
1:49 pm - 6:56 pm
MDW
-
BRD
5h 07m
1 stop
Delta Logo
6:45 am - 12:38 pm
BRD
-
MDW
5h 53m
2 stops
$1,035Delta
Sun, Jul 5 - Sat, Jul 11
Delta Logo
1:18 pm - 6:55 pm
MDW
-
BRD
5h 37m
2 stops
Delta Logo
10:55 am - 6:25 pm
BRD
-
MDW
7h 30m
2 stops
$1,344Delta
Mon, Jul 20 - Mon, Jul 27
Delta Logo
1:49 pm - 6:56 pm
MDW
-
BRD
5h 07m
1 stop
Delta Logo
10:55 am - 6:31 pm
BRD
-
MDW
7h 36m
2 stops
$1,750Delta
Thu, Jul 2 - Sun, Jul 5
Delta Logo
1:26 pm - 6:56 pm
MDW
-
BRD
5h 30m
2 stops
Delta Logo
10:55 am - 6:31 pm
BRD
-
MDW
7h 36m
2 stops
$1,791Delta
Thu, Jul 2 - Sun, Jul 5

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Delta flights from Chicago Midway Airport to Brainerd

Our best Delta deals on Chicago Midway Airport to Brainerd flight tickets
Delta
Jul 4
MDW1:49 pmChicago Midway
5h 07m
1 stop
BRD6:56 pmBrainerd Crow Wing County
Jul 8
BRD6:45 amBrainerd Crow Wing County
5h 53m
2 stops
MDW12:38 pmChicago Midway
$442
Delta
Jul 4
MDW1:26 pmChicago Midway
5h 30m
2 stops
BRD6:56 pmBrainerd Crow Wing County
Jul 8
BRD6:45 amBrainerd Crow Wing County
5h 53m
2 stops
MDW12:38 pmChicago Midway
$447
Delta
Jul 4
MDW1:49 pmChicago Midway
5h 07m
1 stop
BRD6:56 pmBrainerd Crow Wing County
Jul 8
BRD6:45 amBrainerd Crow Wing County
6h 24m
1 stop
MDW1:09 pmChicago Midway
$526

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 June 22, 2026.
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

Cheapest round-trip
Quickest round-trip

ChicagoBrainerd

MDW - BRD

MDWBRD

Chicago Midway

Sat 7/4

1:49 pm-6:56 pm

1 stop5h 07m

Brainerd Crow Wing County

Wed 7/8

6:45 am-12:38 pm

2 stops5h 53m

$442

ChicagoBrainerd

MDW - BRD

MDWBRD

Chicago Midway

Sat 7/4

1:26 pm-6:56 pm

2 stops5h 30m

Brainerd Crow Wing County

Wed 7/8

6:45 am-12:38 pm

2 stops5h 53m

$447

ChicagoBrainerd

MDW - BRD

MDWBRD

Chicago Midway

Sat 7/4

1:49 pm-6:56 pm

1 stop5h 07m

Brainerd Crow Wing County

Wed 7/8

6:45 am-1:09 pm

1 stop6h 24m

$526

ChicagoBrainerd

MDW - BRD

MDWBRD

Chicago Midway

Mon 7/20

1:49 pm-6:55 pm

1 stop5h 06m

Brainerd Crow Wing County

Mon 7/27

6:45 am-1:09 pm

1 stop6h 24m

$624

ChicagoBrainerd

MDW - BRD

MDWBRD

Chicago Midway

Sun 7/5

1:49 pm-6:56 pm

1 stop5h 07m

Brainerd Crow Wing County

Sat 7/11

6:45 am-1:09 pm

1 stop6h 24m

$1,025

ChicagoBrainerd

MDW - BRD

MDWBRD

Chicago Midway

Mon 7/20

1:49 pm-6:55 pm

1 stop5h 06m

Brainerd Crow Wing County

Mon 7/27

10:55 am-6:25 pm

2 stops7h 30m

$1,029

ChicagoBrainerd

MDW - BRD

MDWBRD

Chicago Midway

Sun 7/5

1:49 pm-6:56 pm

1 stop5h 07m

Brainerd Crow Wing County

Sat 7/11

6:45 am-12:38 pm

2 stops5h 53m

$1,035

ChicagoBrainerd

MDW - BRD

MDWBRD

Chicago Midway

Mon 7/20

1:18 pm-6:55 pm

2 stops5h 37m

Brainerd Crow Wing County

Mon 7/27

10:55 am-6:25 pm

2 stops7h 30m

$1,344

ChicagoBrainerd

MDW - BRD

MDWBRD

Chicago Midway

Thu 7/2

1:49 pm-6:56 pm

1 stop5h 07m

Brainerd Crow Wing County

Sun 7/5

10:55 am-6:31 pm

2 stops7h 36m

$1,750

ChicagoBrainerd

MDW - BRD

MDWBRD

Chicago Midway

Thu 7/2

1:26 pm-6:56 pm

2 stops5h 30m

Brainerd Crow Wing County

Sun 7/5

10:55 am-6:31 pm

2 stops7h 36m

$1,791

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 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 airline that flies from Chicago Midway to Brainerd Crow Wing County?

Delta is the most popular carrier operating from Chicago Midway to Brainerd Crow Wing County

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

Fastest flight time

5h 07m

Direct flights

None
The fastest flight from Chicago Midway Airport to Brainerd takes 5h 07m
There are no direct flights from Chicago Midway Airport to Brainerd. There are no popular flight routes from Chicago Midway Airport to Brainerd.
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Brainerd

  • 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 5h 07m, 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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