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Cheap flights from Chicago to Brainerd from $428

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 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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0 bags

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Cheap round-trip flights

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Delta Logo
6:00 am - 10:00 amORD-BRD
4h 00m1 stop
Delta Logo
6:20 pm - 9:56 pmBRD-ORD
3h 36m1 stop
$428Delta
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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
$432Delta
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
$442Delta
Find Deal
Sat, Apr 4 - Wed, Apr 8
Delta Logo
7:00 am - 5:45 pmORD-BRD
10h 45m2 stops
Delta Logo
6:20 pm - 9:56 pmBRD-ORD
3h 36m1 stop
$468Delta
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
$477Delta
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Sat, Apr 4 - Wed, Apr 8
Delta Logo
7:00 am - 5:45 pmORD-BRD
10h 45m2 stops
Delta Logo
6:20 pm - 11:54 pmBRD-ORD
29h 34m2 stops
$568Delta
Find Deal
Sat, Apr 4 - Wed, Apr 8
Delta Logo
6:45 am - 5:43 pmORD-BRD
10h 58m2 stops
Delta Logo
10:55 am - 4:52 pmBRD-ORD
5h 57m1 stop
$578Delta
Find Deal
Fri, Nov 21 - Sun, Nov 23
Delta Logo
1:47 pm - 5:43 pmMDW-BRD
3h 56m1 stop
Delta Logo
10:55 am - 6:08 pmBRD-MDW
7h 13m2 stops
$644Delta
Find Deal
Fri, Nov 21 - Sun, Nov 23
Delta Logo
9:34 am - 5:43 pmMDW-BRD
8h 09m2 stops
Delta Logo
10:55 am - 6:08 pmBRD-MDW
7h 13m2 stops
$979Delta
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Fri, Nov 21 - Sun, Nov 23

Delta flights from Chicago to Brainerd

Our best Delta deals on Chicago to Brainerd flight tickets
Delta
Apr 4
ORD6:00 amChicago O'Hare Intl
4h 00m
1 stop
BRD10:00 amBrainerd Crow Wing County
Apr 8
BRD6:20 pmBrainerd Crow Wing County
3h 36m
1 stop
ORD9:56 pmChicago O'Hare Intl
$428
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
$432
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 15m
2 stops
MDW12:35 pmChicago Midway
$442
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago 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 20, 2025.
Use the filters below to find and compare flights from Chicago to Brainerd that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoBrainerd

ORD - BRD

ORDBRD

Chicago O'Hare Intl

Sat 4/4

6:00 am-10:00 am

1 stop4h 00m

Brainerd Crow Wing County

Wed 4/8

6:20 pm-9:56 pm

1 stop3h 36m

$428

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

$432

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

$442

ChicagoBrainerd

ORD - BRD

ORDBRD

Chicago O'Hare Intl

Sat 4/4

7:00 am-5:45 pm

2 stops10h 45m

Brainerd Crow Wing County

Wed 4/8

6:20 pm-9:56 pm

1 stop3h 36m

$468

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

$477

ChicagoBrainerd

ORD - BRD

ORDBRD

Chicago O'Hare Intl

Sat 4/4

7:00 am-5:45 pm

2 stops10h 45m

Brainerd Crow Wing County

Wed 4/8

6:20 pm-11:54 pm

2 stops29h 34m

$568

ChicagoBrainerd

ORD - BRD

ORDBRD

Chicago O'Hare Intl

Fri 11/21

6:45 am-5:43 pm

2 stops10h 58m

Brainerd Crow Wing County

Sun 11/23

10:55 am-4:52 pm

1 stop5h 57m

$578

ChicagoBrainerd

MDW - BRD

MDWBRD

Chicago Midway

Fri 11/21

1:47 pm-5:43 pm

1 stop3h 56m

Brainerd Crow Wing County

Sun 11/23

10:55 am-6:08 pm

2 stops7h 13m

$644

ChicagoBrainerd

MDW - BRD

MDWBRD

Chicago Midway

Fri 11/21

9:34 am-5:43 pm

2 stops8h 09m

Brainerd Crow Wing County

Sun 11/23

10:55 am-6:08 pm

2 stops7h 13m

$979

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 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 to Brainerd

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

Cheap Chicago to Brainerd (CHI to BRD) flight deals and tips

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

Direct flights

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

    Brainerd Crow Wing County is 449.1 mi away from Chicago. 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 to Brainerd Crow Wing County Airport?

    Prices for flights from Chicago to Brainerd Crow Wing County Airport refresh daily.

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

    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 Chicago to Brainerd Crow Wing County Airport.

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

    The travel and health documents you'll need for your trip to Brainerd Crow Wing County Airport 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 Brainerd Crow Wing County Airport. It is always advisable to seek advice from your airline or a trusted 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?

Flights from Chicago to Brainerd with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once all potential Chicago to Brainerd flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Price alerts on flights to Brainerd from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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