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Cheap flights from Chicago to Brainerd from $332

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 5/28. 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

Enter your travel dates to find the best prices.
Delta Logo
6:24 am - 10:13 am
ORD
-
BRD
3h 49m
1 stop
Delta Logo
10:55 am - 4:51 pm
BRD
-
ORD
5h 56m
1 stop
$332Delta
Thu, May 28 - Sun, May 31
Delta Logo
6:24 am - 10:13 am
ORD
-
BRD
3h 49m
1 stop
Delta Logo
6:45 am - 11:29 am
BRD
-
ORD
4h 44m
1 stop
$368Delta
Fri, Jun 5 - Wed, Jun 10
Delta Logo
6:00 am - 10:00 am
ORD
-
BRD
4h 00m
1 stop
Delta Logo
10:55 am - 4:48 pm
BRD
-
ORD
5h 53m
1 stop
$392Delta
Thu, Jul 2 - Sun, Jul 5
Delta Logo
6:00 am - 10:00 am
ORD
-
BRD
4h 00m
1 stop
Delta Logo
10:55 am - 2:58 pm
BRD
-
ORD
4h 03m
1 stop
$426Delta
Sat, Aug 1 - Sat, Aug 8
Delta Logo
6:00 am - 10:00 am
ORD
-
BRD
4h 00m
1 stop
Delta Logo
10:55 am - 8:24 pm
BRD
-
ORD
9h 29m
2 stops
$436Delta
Sat, Aug 1 - Sat, Aug 8
Delta Logo
6:24 am - 10:13 am
ORD
-
BRD
3h 49m
1 stop
Delta Logo
6:45 am - 1:01 pm
BRD
-
ORD
6h 16m
2 stops
$498Delta
Thu, May 28 - Sun, May 31
Delta Logo
6:24 am - 10:13 am
ORD
-
BRD
3h 49m
1 stop
Delta Logo
6:45 am - 12:39 pm
BRD
-
ORD
5h 54m
2 stops
$624Delta
Fri, Jun 5 - Wed, Jun 10
Delta Logo
10:35 am - 6:55 pm
ORD
-
BRD
8h 20m
2 stops
Delta Logo
10:55 am - 4:48 pm
BRD
-
ORD
5h 53m
1 stop
$666Delta
Thu, Jul 2 - Sun, Jul 5
Delta Logo
11:07 am - 6:56 pm
ORD
-
BRD
7h 49m
2 stops
Delta Logo
6:45 am - 1:01 pm
BRD
-
ORD
6h 16m
2 stops
$785Delta
Thu, May 28 - Sun, May 31
Delta Logo
10:35 am - 6:55 pm
ORD
-
BRD
8h 20m
2 stops
Delta Logo
10:55 am - 8:24 pm
BRD
-
ORD
9h 29m
2 stops
$803Delta
Sat, Aug 1 - Sat, Aug 8

Delta flights from Chicago to Brainerd

Our best Delta deals on Chicago to Brainerd flight tickets
Delta
May 28
ORD6:24 amChicago O'Hare Intl
3h 49m
1 stop
BRD10:13 amBrainerd Crow Wing County
May 31
BRD10:55 amBrainerd Crow Wing County
5h 56m
1 stop
ORD4:51 pmChicago O'Hare Intl
$332
Delta
Aug 1
MDW2:00 pmChicago Midway
4h 55m
1 stop
BRD6:55 pmBrainerd Crow Wing County
Aug 8
BRD6:45 amBrainerd Crow Wing County
6h 22m
1 stop
MDW1:07 pmChicago Midway
$368
Delta
Jul 2
ORD6:00 amChicago O'Hare Intl
4h 00m
1 stop
BRD10:00 amBrainerd Crow Wing County
Jul 5
BRD10:55 amBrainerd Crow Wing County
5h 53m
1 stop
ORD4:48 pmChicago O'Hare Intl
$392

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 March 11, 2026.
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

Cheapest round-trip

ChicagoBrainerd

ORD - BRD

ORDBRD

Chicago O'Hare Intl

Thu 5/28

6:24 am-10:13 am

1 stop3h 49m

Brainerd Crow Wing County

Sun 5/31

10:55 am-4:51 pm

1 stop5h 56m

$332

ChicagoBrainerd

ORD - BRD

ORDBRD

Chicago O'Hare Intl

Fri 6/5

6:24 am-10:13 am

1 stop3h 49m

Brainerd Crow Wing County

Wed 6/10

6:45 am-11:29 am

1 stop4h 44m

$368

ChicagoBrainerd

ORD - BRD

ORDBRD

Chicago O'Hare Intl

Thu 7/2

6:00 am-10:00 am

1 stop4h 00m

Brainerd Crow Wing County

Sun 7/5

10:55 am-4:48 pm

1 stop5h 53m

$392
Quickest round-trip

ChicagoBrainerd

ORD - BRD

ORDBRD

Chicago O'Hare Intl

Sat 8/1

6:00 am-10:00 am

1 stop4h 00m

Brainerd Crow Wing County

Sat 8/8

10:55 am-2:58 pm

1 stop4h 03m

$426

ChicagoBrainerd

ORD - BRD

ORDBRD

Chicago O'Hare Intl

Sat 8/1

6:00 am-10:00 am

1 stop4h 00m

Brainerd Crow Wing County

Sat 8/8

10:55 am-8:24 pm

2 stops9h 29m

$436

ChicagoBrainerd

ORD - BRD

ORDBRD

Chicago O'Hare Intl

Thu 5/28

6:24 am-10:13 am

1 stop3h 49m

Brainerd Crow Wing County

Sun 5/31

6:45 am-1:01 pm

2 stops6h 16m

$498

ChicagoBrainerd

ORD - BRD

ORDBRD

Chicago O'Hare Intl

Fri 6/5

6:24 am-10:13 am

1 stop3h 49m

Brainerd Crow Wing County

Wed 6/10

6:45 am-12:39 pm

2 stops5h 54m

$624

ChicagoBrainerd

ORD - BRD

ORDBRD

Chicago O'Hare Intl

Thu 7/2

10:35 am-6:55 pm

2 stops8h 20m

Brainerd Crow Wing County

Sun 7/5

10:55 am-4:48 pm

1 stop5h 53m

$666

ChicagoBrainerd

ORD - BRD

ORDBRD

Chicago O'Hare Intl

Thu 5/28

11:07 am-6:56 pm

2 stops7h 49m

Brainerd Crow Wing County

Sun 5/31

6:45 am-1:01 pm

2 stops6h 16m

$785

ChicagoBrainerd

ORD - BRD

ORDBRD

Chicago O'Hare Intl

Sat 8/1

10:35 am-6:55 pm

2 stops8h 20m

Brainerd Crow Wing County

Sat 8/8

10:55 am-8:24 pm

2 stops9h 29m

$803

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 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 to Brainerd Crow Wing County?

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

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

Fastest flight time

3h 49m

Direct flights

None
The fastest flight from Chicago to Brainerd takes 3h 49m
There are no direct flights from Chicago to Brainerd. There are no popular flight routes from Chicago to Brainerd.
Search flight deals

  • 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 49m, 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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