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Cheap flights from Chicago Midway Airport to Brainerd from $181

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 4/21. 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

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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
2:05 pm - 6:55 pm
MDW
-
BRD
4h 50m
1 stop
Delta Logo
6:45 am - 12:29 pm
BRD
-
MDW
5h 44m
2 stops
$578Delta
Fri, Apr 3 - Tue, Apr 7
Delta Logo
1:10 pm - 6:55 pm
MDW
-
BRD
5h 45m
2 stops
Delta Logo
6:45 am - 12:29 pm
BRD
-
MDW
5h 44m
2 stops
$719Delta
Fri, Apr 3 - Tue, Apr 7
Delta Logo
2:05 pm - 6:55 pm
MDW
-
BRD
4h 50m
1 stop
Delta Logo
10:55 am - 5:54 pm
BRD
-
MDW
6h 59m
2 stops
$947Delta
Sun, Apr 5 - Thu, Apr 9
Delta Logo
1:10 pm - 6:55 pm
MDW
-
BRD
5h 45m
2 stops
Delta Logo
10:55 am - 5:54 pm
BRD
-
MDW
6h 59m
2 stops
$1,315Delta
Sun, Apr 5 - Thu, Apr 9

Delta flights from Chicago Midway Airport to Brainerd

Our best Delta deals on Chicago Midway Airport to Brainerd flight tickets
Delta
Apr 3
MDW2:05 pmChicago Midway
4h 50m
1 stop
BRD6:55 pmBrainerd Crow Wing County
Apr 7
BRD6:45 amBrainerd Crow Wing County
5h 44m
2 stops
MDW12:29 pmChicago Midway
$578
Delta
Apr 3
MDW1:10 pmChicago Midway
5h 45m
2 stops
BRD6:55 pmBrainerd Crow Wing County
Apr 7
BRD6:45 amBrainerd Crow Wing County
5h 44m
2 stops
MDW12:29 pmChicago Midway
$719
Delta
Apr 5
MDW2:05 pmChicago Midway
4h 50m
1 stop
BRD6:55 pmBrainerd Crow Wing County
Apr 9
BRD10:55 amBrainerd Crow Wing County
6h 59m
2 stops
MDW5:54 pmChicago Midway
$947

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 March 21, 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

Fri 4/3

2:05 pm-6:55 pm

1 stop4h 50m

Brainerd Crow Wing County

Tue 4/7

6:45 am-12:29 pm

2 stops5h 44m

$578

ChicagoBrainerd

MDW - BRD

MDWBRD

Chicago Midway

Fri 4/3

1:10 pm-6:55 pm

2 stops5h 45m

Brainerd Crow Wing County

Tue 4/7

6:45 am-12:29 pm

2 stops5h 44m

$719

ChicagoBrainerd

MDW - BRD

MDWBRD

Chicago Midway

Sun 4/5

2:05 pm-6:55 pm

1 stop4h 50m

Brainerd Crow Wing County

Thu 4/9

10:55 am-5:54 pm

2 stops6h 59m

$947

ChicagoBrainerd

MDW - BRD

MDWBRD

Chicago Midway

Sun 4/5

1:10 pm-6:55 pm

2 stops5h 45m

Brainerd Crow Wing County

Thu 4/9

10:55 am-5:54 pm

2 stops6h 59m

$1,315
Cheapest one-way

ChicagoBrainerd

MDW - BRD

MDWBRD

Chicago Midway

Tue 4/21

7:16 pm-7:00 pm

1 stop23h 44m

$181

ChicagoBrainerd

MDW - BRD

MDWBRD

Chicago Midway

Mon 4/20

9:29 am-7:00 pm

1 stop9h 31m

$211
Quickest one-way

ChicagoBrainerd

MDW - BRD

MDWBRD

Chicago Midway

Wed 6/24

2:00 pm-6:55 pm

1 stop4h 55m

$268

ChicagoBrainerd

MDW - BRD

MDWBRD

Chicago Midway

Wed 4/22

9:27 am-7:00 pm

2 stops9h 33m

$341

ChicagoBrainerd

MDW - BRD

MDWBRD

Chicago Midway

Tue 4/21

9:27 am-7:00 pm

2 stops9h 33m

$421

ChicagoBrainerd

MDW - BRD

MDWBRD

Chicago Midway

Mon 4/20

9:27 am-7:00 pm

2 stops9h 33m

$471

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 11 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

4h 50m

Direct flights

None
The fastest flight from Chicago Midway Airport to Brainerd takes 4h 50m
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

  • 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 4h 50m, 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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Mon 4/20
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