Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Brainerd to Chicago from $272

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 7/22. 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
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 - 4:48 pm
BRD
-
ORD
5h 53m
1 stop
Delta Logo
5:20 pm - 8:45 pm
ORD
-
BRD
3h 25m
1 stop
$352Delta
Sat, Oct 3 - Mon, Oct 5
Delta Logo
6:45 am - 12:39 pm
BRD
-
ORD
5h 54m
2 stops
Delta Logo
5:20 pm - 8:45 pm
ORD
-
BRD
3h 25m
1 stop
$362Delta
Sat, Oct 3 - Mon, Oct 5
Delta Logo
6:45 am - 11:47 am
BRD
-
ORD
5h 02m
1 stop
Delta Logo
6:24 am - 10:13 am
ORD
-
BRD
3h 49m
1 stop
$402Delta
Wed, May 20 - Mon, May 25
Delta Logo
6:45 am - 1:01 pm
BRD
-
ORD
6h 16m
2 stops
Delta Logo
6:24 am - 10:13 am
ORD
-
BRD
3h 49m
1 stop
$442Delta
Wed, May 20 - Sun, May 24
Delta Logo
6:45 am - 12:42 pm
BRD
-
MDW
5h 57m
2 stops
Delta Logo
1:59 pm - 6:56 pm
MDW
-
BRD
4h 57m
1 stop
$448Delta
Sat, May 30 - Mon, Jun 1
Delta Logo
6:45 am - 11:47 am
BRD
-
ORD
5h 02m
1 stop
Delta Logo
6:24 am - 10:13 am
ORD
-
BRD
3h 49m
1 stop
$468Delta
Wed, May 20 - Sun, May 24
Delta Logo
6:45 am - 12:56 pm
BRD
-
ORD
6h 11m
2 stops
Delta Logo
6:24 am - 10:13 am
ORD
-
BRD
3h 49m
1 stop
$478Delta
Sat, May 30 - Mon, Jun 1
Delta Logo
10:55 am - 3:05 pm
BRD
-
ORD
4h 10m
1 stop
Delta Logo
6:30 am - 10:13 am
ORD
-
BRD
3h 43m
1 stop
$496Delta
Thu, Jun 18 - Mon, Jun 22
Delta Logo
6:45 am - 1:01 pm
BRD
-
ORD
6h 16m
2 stops
Delta Logo
6:24 am - 10:13 am
ORD
-
BRD
3h 49m
1 stop
$516Delta
Wed, May 20 - Mon, May 25
Delta Logo
6:45 am - 12:42 pm
BRD
-
MDW
5h 57m
2 stops
Delta Logo
1:22 pm - 6:56 pm
MDW
-
BRD
5h 34m
2 stops
$521Delta
Sat, May 30 - Mon, Jun 1

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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
5h 53m
1 stop
ORD4:48 pmChicago O'Hare Intl
Oct 5
ORD5:20 pmChicago O'Hare Intl
3h 25m
1 stop
BRD8:45 pmBrainerd Crow Wing County
$352
Delta
Oct 3
BRD6:45 amBrainerd Crow Wing County
5h 54m
2 stops
ORD12:39 pmChicago O'Hare Intl
Oct 5
ORD5:20 pmChicago O'Hare Intl
3h 25m
1 stop
BRD8:45 pmBrainerd Crow Wing County
$362
Delta
May 30
BRD10:55 amBrainerd Crow Wing County
4h 02m
1 stop
ORD2:57 pmChicago O'Hare Intl
Jun 1
ORD6:24 amChicago O'Hare Intl
3h 49m
1 stop
BRD10:13 amBrainerd Crow Wing County
$372

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 May 6, 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-4:48 pm

1 stop5h 53m

Chicago O'Hare Intl

Mon 10/5

5:20 pm-8:45 pm

1 stop3h 25m

$352

BrainerdChicago

BRD - ORD

BRDORD

Brainerd Crow Wing County

Sat 10/3

6:45 am-12:39 pm

2 stops5h 54m

Chicago O'Hare Intl

Mon 10/5

5:20 pm-8:45 pm

1 stop3h 25m

$362

BrainerdChicago

BRD - ORD

BRDORD

Brainerd Crow Wing County

Wed 5/20

6:45 am-11:47 am

1 stop5h 02m

Chicago O'Hare Intl

Mon 5/25

6:24 am-10:13 am

1 stop3h 49m

$402

BrainerdChicago

BRD - ORD

BRDORD

Brainerd Crow Wing County

Wed 5/20

6:45 am-1:01 pm

2 stops6h 16m

Chicago O'Hare Intl

Sun 5/24

6:24 am-10:13 am

1 stop3h 49m

$442

BrainerdChicago

BRD - MDW

BRDMDW

Brainerd Crow Wing County

Sat 5/30

6:45 am-12:42 pm

2 stops5h 57m

Chicago Midway

Mon 6/1

1:59 pm-6:56 pm

1 stop4h 57m

$448

BrainerdChicago

BRD - ORD

BRDORD

Brainerd Crow Wing County

Wed 5/20

6:45 am-11:47 am

1 stop5h 02m

Chicago O'Hare Intl

Sun 5/24

6:24 am-10:13 am

1 stop3h 49m

$468

BrainerdChicago

BRD - ORD

BRDORD

Brainerd Crow Wing County

Sat 5/30

6:45 am-12:56 pm

2 stops6h 11m

Chicago O'Hare Intl

Mon 6/1

6:24 am-10:13 am

1 stop3h 49m

$478
Quickest round-trip

BrainerdChicago

BRD - ORD

BRDORD

Brainerd Crow Wing County

Thu 6/18

10:55 am-3:05 pm

1 stop4h 10m

Chicago O'Hare Intl

Mon 6/22

6:30 am-10:13 am

1 stop3h 43m

$496

BrainerdChicago

BRD - ORD

BRDORD

Brainerd Crow Wing County

Wed 5/20

6:45 am-1:01 pm

2 stops6h 16m

Chicago O'Hare Intl

Mon 5/25

6:24 am-10:13 am

1 stop3h 49m

$516

BrainerdChicago

BRD - MDW

BRDMDW

Brainerd Crow Wing County

Sat 5/30

6:45 am-12:42 pm

2 stops5h 57m

Chicago Midway

Mon 6/1

1:22 pm-6:56 pm

2 stops5h 34m

$521

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
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.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Fri 6/5
Fri 6/12
By creating a price alert you accept our terms of use and privacy policy.

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