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Cheap flights from Chicago to Brainerd from $268

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 to Brainerd departing on 6/28. 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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Find the cheapest flights from Chicago to Brainerd

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
2:00 pm - 7:20 pm
MDW
-
BRD
5h 20m
1 stop
Delta Logo
6:45 am - 1:11 pm
BRD
-
MDW
6h 26m
1 stop
$342Delta
qua, ago 19 - dom, ago 23
Delta Logo
2:00 pm - 7:20 pm
MDW
-
BRD
5h 20m
1 stop
Delta Logo
6:45 am - 12:30 pm
BRD
-
MDW
5h 45m
2 stops
$352Delta
qua, ago 19 - dom, ago 23
Delta Logo
6:30 am - 10:00 am
ORD
-
BRD
3h 30m
1 stop
Delta Logo
10:55 am - 5:02 pm
BRD
-
ORD
6h 07m
1 stop
$352Delta
qui, jun 11 - sáb, jun 13
Delta Logo
1:00 pm - 7:20 pm
MDW
-
BRD
6h 20m
2 stops
Delta Logo
6:45 am - 12:30 pm
BRD
-
MDW
5h 45m
2 stops
$357Delta
qua, ago 19 - dom, ago 23
Delta Logo
6:30 am - 10:00 am
ORD
-
BRD
3h 30m
1 stop
Delta Logo
6:45 am - 1:53 pm
BRD
-
ORD
7h 08m
2 stops
$362Delta
qui, jun 11 - sáb, jun 13
Delta Logo
9:25 am - 6:56 pm
ORD
-
BRD
9h 31m
2 stops
Delta Logo
10:55 am - 2:57 pm
BRD
-
ORD
4h 02m
1 stop
$372Delta
qua, mai 20 - dom, mai 24
Delta Logo
9:25 am - 6:56 pm
ORD
-
BRD
9h 31m
2 stops
Delta Logo
6:45 am - 12:56 pm
BRD
-
ORD
6h 11m
2 stops
$377Delta
qua, mai 20 - dom, mai 24
Delta Logo
6:30 am - 10:00 am
ORD
-
BRD
3h 30m
1 stop
Delta Logo
10:55 am - 5:02 pm
BRD
-
ORD
6h 07m
1 stop
$388Delta
qui, jun 11 - sáb, jun 13
Delta Logo
11:30 am - 7:20 pm
ORD
-
BRD
7h 50m
2 stops
Delta Logo
6:45 am - 12:39 pm
BRD
-
ORD
5h 54m
2 stops
$393Delta
qua, ago 19 - dom, ago 23
Delta Logo
1:59 pm - 6:56 pm
MDW
-
BRD
4h 57m
1 stop
Delta Logo
6:45 am - 12:42 pm
BRD
-
MDW
5h 57m
2 stops
$398Delta
dom, mai 24 - sáb, mai 30

Delta flights from Chicago to Brainerd

Our best Delta deals on Chicago to Brainerd flight tickets
Delta
Aug 19
MDW2:00 pmChicago Midway
5h 20m
1 stop
BRD7:20 pmBrainerd Crow Wing County
Aug 23
BRD6:45 amBrainerd Crow Wing County
6h 26m
1 stop
MDW1:11 pmChicago Midway
$342
Delta
Aug 19
MDW2:00 pmChicago Midway
5h 20m
1 stop
BRD7:20 pmBrainerd Crow Wing County
Aug 23
BRD6:45 amBrainerd Crow Wing County
5h 45m
2 stops
MDW12:30 pmChicago Midway
$352
Delta
Aug 19
MDW1:00 pmChicago Midway
6h 20m
2 stops
BRD7:20 pmBrainerd Crow Wing County
Aug 23
BRD6:45 amBrainerd Crow Wing County
5h 45m
2 stops
MDW12:30 pmChicago Midway
$357

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 abril 25, 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

MDW - BRD

MDWBRD

Chicago Midway

qua 8/19

2:00 pm-7:20 pm

1 stop5h 20m

Brainerd Crow Wing County

dom 8/23

6:45 am-1:11 pm

1 stop6h 26m

$342

ChicagoBrainerd

MDW - BRD

MDWBRD

Chicago Midway

qua 8/19

2:00 pm-7:20 pm

1 stop5h 20m

Brainerd Crow Wing County

dom 8/23

6:45 am-12:30 pm

2 stops5h 45m

$352
Quickest round-trip

ChicagoBrainerd

ORD - BRD

ORDBRD

Chicago O'Hare Intl

qui 6/11

6:30 am-10:00 am

1 stop3h 30m

Brainerd Crow Wing County

sáb 6/13

10:55 am-5:02 pm

1 stop6h 07m

$352

ChicagoBrainerd

MDW - BRD

MDWBRD

Chicago Midway

qua 8/19

1:00 pm-7:20 pm

2 stops6h 20m

Brainerd Crow Wing County

dom 8/23

6:45 am-12:30 pm

2 stops5h 45m

$357

ChicagoBrainerd

ORD - BRD

ORDBRD

Chicago O'Hare Intl

qui 6/11

6:30 am-10:00 am

1 stop3h 30m

Brainerd Crow Wing County

sáb 6/13

6:45 am-1:53 pm

2 stops7h 08m

$362

ChicagoBrainerd

ORD - BRD

ORDBRD

Chicago O'Hare Intl

qua 5/20

9:25 am-6:56 pm

2 stops9h 31m

Brainerd Crow Wing County

dom 5/24

10:55 am-2:57 pm

1 stop4h 02m

$372

ChicagoBrainerd

ORD - BRD

ORDBRD

Chicago O'Hare Intl

qua 5/20

9:25 am-6:56 pm

2 stops9h 31m

Brainerd Crow Wing County

dom 5/24

6:45 am-12:56 pm

2 stops6h 11m

$377

ChicagoBrainerd

ORD - BRD

ORDBRD

Chicago O'Hare Intl

qui 6/11

6:30 am-10:00 am

1 stop3h 30m

Brainerd Crow Wing County

sáb 6/13

10:55 am-5:02 pm

1 stop6h 07m

$388

ChicagoBrainerd

ORD - BRD

ORDBRD

Chicago O'Hare Intl

qua 8/19

11:30 am-7:20 pm

2 stops7h 50m

Brainerd Crow Wing County

dom 8/23

6:45 am-12:39 pm

2 stops5h 54m

$393

ChicagoBrainerd

MDW - BRD

MDWBRD

Chicago Midway

dom 5/24

1:59 pm-6:56 pm

1 stop4h 57m

Brainerd Crow Wing County

sáb 5/30

6:45 am-12:42 pm

2 stops5h 57m

$398

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 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 30m

Direct flights

None
The fastest flight from Chicago to Brainerd takes 3h 30m
There are no direct flights from Chicago to Brainerd. There are no popular flight routes from Chicago to Brainerd.
Search flight deals

Frequently asked questions about flying from Chicago to Brainerd

  • 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 30m, 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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