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Cheap flights from Brainerd to Chicago from $312

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Brainerd to Chicago departing on 7/8. 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

Find the cheapest flights from Brainerd to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
10:55 am - 3:05 pm
BRD
-
ORD
4h 10m
1 stop
Delta Logo
3:55 pm - 8:45 pm
ORD
-
BRD
4h 50m
1 stop
$352Delta
Sat, Oct 3 - Mon, Oct 5
Delta Logo
6:45 am - 1:13 pm
BRD
-
ORD
6h 28m
2 stops
Delta Logo
6:00 am - 10:00 am
ORD
-
BRD
4h 00m
1 stop
$398Delta
Sat, Oct 3 - Mon, Oct 5
Delta Logo
6:45 am - 11:32 am
BRD
-
ORD
4h 47m
1 stop
Delta Logo
6:30 am - 10:18 am
ORD
-
BRD
3h 48m
1 stop
$432Delta
Wed, Jul 8 - Sun, Jul 12
Delta Logo
6:45 am - 1:13 pm
BRD
-
ORD
6h 28m
2 stops
Delta Logo
6:00 am - 10:00 am
ORD
-
BRD
4h 00m
1 stop
$438Delta
Sat, Oct 3 - Mon, Oct 5
Delta Logo
6:45 am - 1:03 pm
BRD
-
ORD
6h 18m
2 stops
Delta Logo
6:30 am - 10:18 am
ORD
-
BRD
3h 48m
1 stop
$442Delta
Wed, Jul 8 - Sun, Jul 12
Delta Logo
6:45 am - 11:42 am
BRD
-
ORD
4h 57m
1 stop
Delta Logo
5:20 pm - 8:45 pm
ORD
-
BRD
3h 25m
1 stop
$486Delta
Wed, Nov 25 - Sat, Nov 28
Delta Logo
6:45 am - 1:13 pm
BRD
-
ORD
6h 28m
2 stops
Delta Logo
6:00 am - 10:00 am
ORD
-
BRD
4h 00m
1 stop
$496Delta
Sat, Oct 3 - Mon, Oct 5
Delta Logo
6:45 am - 11:32 am
BRD
-
ORD
4h 47m
1 stop
Delta Logo
12:46 pm - 6:55 pm
ORD
-
BRD
6h 09m
1 stop
$538Delta
Wed, Jul 29 - Sat, Aug 1
Delta Logo
6:45 am - 1:03 pm
BRD
-
ORD
6h 18m
2 stops
Delta Logo
12:46 pm - 6:55 pm
ORD
-
BRD
6h 09m
1 stop
$558Delta
Thu, Jul 30 - Sat, Aug 1
Delta Logo
6:45 am - 11:32 am
BRD
-
ORD
4h 47m
1 stop
Delta Logo
6:30 am - 10:18 am
ORD
-
BRD
3h 48m
1 stop
$606Delta
Thu, Jul 30 - Sat, Aug 1

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Delta flights from Brainerd to Chicago

Our best Delta deals on Brainerd to Chicago flight tickets
Delta
Oct 3
BRD10:55 amBrainerd Crow Wing County
4h 10m
1 stop
ORD3:05 pmChicago O'Hare Intl
Oct 5
ORD3:55 pmChicago O'Hare Intl
4h 50m
1 stop
BRD8:45 pmBrainerd Crow Wing County
$352
Delta
Oct 3
BRD6:45 amBrainerd Crow Wing County
6h 28m
2 stops
ORD1:13 pmChicago O'Hare Intl
Oct 5
ORD6:00 amChicago O'Hare Intl
4h 00m
1 stop
BRD10:00 amBrainerd Crow Wing County
$398
Delta
Jul 8
BRD6:45 amBrainerd Crow Wing County
4h 47m
1 stop
ORD11:32 amChicago O'Hare Intl
Jul 12
ORD6:30 amChicago O'Hare Intl
3h 48m
1 stop
BRD10:18 amBrainerd Crow Wing County
$432

momondo Fare Finder

 
Customize your flight search to find flights from Brainerd to Chicago 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 June 25, 2026.
Use the filters below to find and compare flights from Brainerd to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BrainerdChicago

BRD - ORD

BRDORD

Brainerd Crow Wing County

Sat 10/3

10:55 am-3:05 pm

1 stop4h 10m

Chicago O'Hare Intl

Mon 10/5

3:55 pm-8:45 pm

1 stop4h 50m

$352

BrainerdChicago

BRD - ORD

BRDORD

Brainerd Crow Wing County

Sat 10/3

6:45 am-1:13 pm

2 stops6h 28m

Chicago O'Hare Intl

Mon 10/5

6:00 am-10:00 am

1 stop4h 00m

$398

BrainerdChicago

BRD - ORD

BRDORD

Brainerd Crow Wing County

Wed 7/8

6:45 am-11:32 am

1 stop4h 47m

Chicago O'Hare Intl

Sun 7/12

6:30 am-10:18 am

1 stop3h 48m

$432

BrainerdChicago

BRD - ORD

BRDORD

Brainerd Crow Wing County

Sat 10/3

6:45 am-1:13 pm

2 stops6h 28m

Chicago O'Hare Intl

Mon 10/5

6:00 am-10:00 am

1 stop4h 00m

$438

BrainerdChicago

BRD - ORD

BRDORD

Brainerd Crow Wing County

Wed 7/8

6:45 am-1:03 pm

2 stops6h 18m

Chicago O'Hare Intl

Sun 7/12

6:30 am-10:18 am

1 stop3h 48m

$442
Quickest round-trip

BrainerdChicago

BRD - ORD

BRDORD

Brainerd Crow Wing County

Wed 11/25

6:45 am-11:42 am

1 stop4h 57m

Chicago O'Hare Intl

Sat 11/28

5:20 pm-8:45 pm

1 stop3h 25m

$486

BrainerdChicago

BRD - ORD

BRDORD

Brainerd Crow Wing County

Sat 10/3

6:45 am-1:13 pm

2 stops6h 28m

Chicago O'Hare Intl

Mon 10/5

6:00 am-10:00 am

1 stop4h 00m

$496

BrainerdChicago

BRD - ORD

BRDORD

Brainerd Crow Wing County

Wed 7/29

6:45 am-11:32 am

1 stop4h 47m

Chicago O'Hare Intl

Sat 8/1

12:46 pm-6:55 pm

1 stop6h 09m

$538

BrainerdChicago

BRD - ORD

BRDORD

Brainerd Crow Wing County

Thu 7/30

6:45 am-1:03 pm

2 stops6h 18m

Chicago O'Hare Intl

Sat 8/1

12:46 pm-6:55 pm

1 stop6h 09m

$558

BrainerdChicago

BRD - ORD

BRDORD

Brainerd Crow Wing County

Thu 7/30

6:45 am-11:32 am

1 stop4h 47m

Chicago O'Hare Intl

Sat 8/1

6:30 am-10:18 am

1 stop3h 48m

$606

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Brainerd to Chicago

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 Brainerd Crow Wing County to Chicago?

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

When to book flights from Brainerd to Chicago

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

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

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

Fastest flight time

4h 10m

Direct flights

None
The fastest flight from Brainerd to Chicago takes 4h 10m
There are no direct flights from Brainerd to Chicago. There are no popular flight routes from Brainerd to Chicago.
Search flight deals

Frequently asked questions about flying from Brainerd to Chicago

  • How far is Brainerd Crow Wing County to Chicago by plane?

    Chicago is 449.1 mi away from Brainerd Crow Wing County. A reasonable flight in good conditions will take 4h 10m.

  • When did momondo last update prices for flights from Brainerd Crow Wing County Airport to Chicago?

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

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

    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 Brainerd Crow Wing County Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Brainerd to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Brainerd to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Brainerd to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Brainerd with this policy.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Brainerd.

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

Price alerts on flights to Chicago from Brainerd 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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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport