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Brainerd

$248+ Cheap flights from Chicago (CHI) to Brainerd (BRD)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BRD
Mar 6 — Mar 131
Fri 3/6
Fri 3/13
1 adult, Economy
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Cheap flight deals from Chicago to Brainerd

Cheapest flights from Chicago to Brainerd
Explore the most affordable flight options available from Chicago to Brainerd. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 4, 2026.

This Delta deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/12:00 pm
MDW
-
BRD
1 stop4h 55m
Delta
Sun 8/96:45 am
BRD
-
MDW
1 stop6h 22m
Delta
Deal found 2/3$388
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/256:00 am
ORD
-
BRD
1 stop4h 00m
Delta
Sun 6/2810:55 am
BRD
-
ORD
1 stop5h 53m
Delta
Deal found 2/1$388
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/171:49 pm
MDW
-
BRD
1 stop3h 51m
Delta
Sat 2/2111:00 am
BRD
-
MDW
1 stop5h 14m
Delta
Deal found 2/2$392
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/1712:29 pm
ORD
-
BRD
1 stop5h 11m
Delta
Sat 2/216:15 pm
BRD
-
ORD
1 stop3h 15m
Delta
Deal found 2/2$392
This Delta deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/16:00 am
ORD
-
BRD
1 stop4h 00m
Delta
Sun 8/96:45 am
BRD
-
ORD
1 stop4h 44m
Delta
Deal found 2/3$426
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/252:00 pm
MDW
-
BRD
1 stop4h 55m
Delta
Sun 6/286:45 am
BRD
-
MDW
1 stop6h 22m
Delta
Deal found 2/1$488
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/166:15 am
ORD
-
BRD
1 stop4h 07m
Delta
Fri 2/206:15 pm
BRD
-
ORD
1 stop3h 15m
Delta
Deal found 2/1$600
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/161:49 pm
MDW
-
BRD
1 stop3h 51m
Delta
Fri 2/2011:00 am
BRD
-
MDW
2 stops6h 37m
Delta
Deal found 2/1$610
This Delta deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/176:30 am
ORD
-
BRD
2 stops11h 10m
Delta
Fri 2/2011:00 am
BRD
-
ORD
2 stops5h 41m
Delta
Deal found 2/3$923

Find flight deals from Chicago to Brainerd

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Brainerd (BRD). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated February 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$388
(Delta)

One-way from

$248
(Delta)
Provider with most accurate pricing for Chicago (CHI)-Brainerd Crow Wing County flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Brainerd Crow Wing County flights.
Search Deals
From Chicago (CHI) to Brainerd Crow Wing County
Search Deals
One-way flight from Chicago (CHI) to Brainerd Crow Wing County
Search Deals

Cheapflights 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, Cheapflights users made 2,558,603 searches. Data last updated February 4, 2026.
Use the filters below to find and compare flights from Chicago to Brainerd that are best for you.

Fly from

Chicago

Fly to

Brainerd

Route

Depart

Return

Price

ChicagoBrainerd

MDW - BRD

MDWBRD

Chicago Midway

Sat 8/1

2:00 pm-6:55 pm

1 stop4h 55m

Brainerd Crow Wing County

Sun 8/9

6:45 am-1:07 pm

1 stop6h 22m

$388

ChicagoBrainerd

MDW - BRD

MDWBRD

Chicago Midway

Tue 2/17

1:49 pm-5:40 pm

1 stop3h 51m

Brainerd Crow Wing County

Sat 2/21

11:00 am-4:14 pm

1 stop5h 14m

$392

ChicagoBrainerd

ORD - BRD

ORDBRD

Chicago O'Hare Intl

Sat 8/1

6:00 am-10:00 am

1 stop4h 00m

Brainerd Crow Wing County

Sun 8/9

6:45 am-11:29 am

1 stop4h 44m

$426

ChicagoBrainerd

MDW - BRD

MDWBRD

Chicago Midway

Thu 6/25

2:00 pm-6:55 pm

1 stop4h 55m

Brainerd Crow Wing County

Sun 6/28

6:45 am-1:07 pm

1 stop6h 22m

$488

ChicagoBrainerd

ORD - BRD

ORDBRD

Chicago O'Hare Intl

Mon 2/16

6:15 am-10:22 am

1 stop4h 07m

Brainerd Crow Wing County

Fri 2/20

6:15 pm-9:30 pm

1 stop3h 15m

$600

ChicagoBrainerd

ORD - BRD

ORDBRD

Chicago O'Hare Intl

Tue 2/17

12:29 pm-5:40 pm

1 stop5h 11m

Brainerd Crow Wing County

Fri 2/20

6:15 pm-9:30 pm

1 stop3h 15m

$600

ChicagoBrainerd

MDW - BRD

MDWBRD

Chicago Midway

Mon 2/16

1:49 pm-5:40 pm

1 stop3h 51m

Brainerd Crow Wing County

Fri 2/20

11:00 am-5:37 pm

2 stops6h 37m

$610

ChicagoBrainerd

ORD - BRD

ORDBRD

Chicago O'Hare Intl

Thu 6/25

6:00 am-10:00 am

1 stop4h 00m

Brainerd Crow Wing County

Sun 6/28

6:45 am-12:39 pm

2 stops5h 54m

$744

ChicagoBrainerd

ORD - BRD

ORDBRD

Chicago O'Hare Intl

Tue 2/17

12:29 pm-5:40 pm

1 stop5h 11m

Brainerd Crow Wing County

Sat 2/21

11:00 am-4:41 pm

2 stops5h 41m

$764

ChicagoBrainerd

MDW - BRD

MDWBRD

Chicago Midway

Sat 8/1

2:00 pm-6:55 pm

1 stop4h 55m

$248

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/3

Showing 1-10 of 11 results
1
2
  • Most accurate provider: When it comes to deals on Chicago-Brainerd flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Brainerd flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Brainerd flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Brainerd flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Brainerd flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Brainerd

Have a flexible travel schedule? Discover the best time to fly to Brainerd from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Brainerd
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Brainerd. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Brainerd from Chicago?

    Located just 4.1 mi from the city center, Brainerd Crow Wing County is the airport most travelers will use when flying to Brainerd from Chicago. Booking flights from Chicago to Crow Wing County (BRD) should be relatively easy as there are 0 daily inbound flights from Chicago from 0 different airlines.

  • How long is the flight from Chicago to Brainerd?

    Airlines like Delta fly from Chicago to Brainerd in about 4h 55m. The time it takes to get you to your destination can typically vary by up to . The distance between Chicago and Brainerd is about 449 mi.

  • Can I find deals for flights from Chicago to Brainerd that include hotel bookings?

    Yes. In addition to deals on Chicago to Brainerd flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Brainerd?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Brainerd.

  • Can I find deals for business class flights from Chicago to Brainerd?

    Yes. Cheapflights offers flight deals from Chicago to Brainerd by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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