Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Brainerd to Chicago from $253

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 11/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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

Find the cheapest flights from Brainerd to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:20 pm - 9:19 pmBRD-ORD
2h 59m1 stop
Delta Logo
11:13 am - 5:42 pmORD-BRD
6h 29m1 stop
$639Delta
Find Deal
Mon, Oct 27 - Fri, Oct 31
Delta Logo
6:20 pm - 9:19 pmBRD-ORD
2h 59m1 stop
Delta Logo
5:08 am - 9:09 amORD-BRD
4h 01m1 stop
$654Delta
Find Deal
Wed, Oct 29 - Sun, Nov 2
Delta Logo
6:20 pm - 9:19 pmBRD-ORD
2h 59m1 stop
Delta Logo
8:55 am - 5:42 pmORD-BRD
8h 47m2 stops
$754Delta
Find Deal
Wed, Oct 29 - Sun, Nov 2
Delta Logo
10:55 am - 6:14 pmBRD-ORD
7h 19m2 stops
Delta Logo
11:13 am - 5:42 pmORD-BRD
6h 29m1 stop
$779Delta
Find Deal
Mon, Oct 27 - Fri, Oct 31
Delta Logo
10:55 am - 6:25 pmBRD-MDW
7h 30m2 stops
Delta Logo
9:35 am - 5:42 pmMDW-BRD
8h 07m2 stops
$971Delta
Find Deal
Mon, Oct 27 - Fri, Oct 31

Delta flights from Brainerd to Chicago

Our best Delta deals on Brainerd to Chicago flight tickets
Delta
Oct 27
BRD6:20 pmBrainerd Crow Wing County
2h 59m
1 stop
ORD9:19 pmChicago O'Hare Intl
Oct 31
ORD11:13 amChicago O'Hare Intl
6h 29m
1 stop
BRD5:42 pmBrainerd Crow Wing County
$639
Find similar
Delta
Oct 29
BRD6:20 pmBrainerd Crow Wing County
2h 59m
1 stop
ORD9:19 pmChicago O'Hare Intl
Nov 2
ORD5:08 amChicago O'Hare Intl
4h 01m
1 stop
BRD9:09 amBrainerd Crow Wing County
$654
Find similar
Delta
Oct 29
BRD6:20 pmBrainerd Crow Wing County
2h 59m
1 stop
ORD9:19 pmChicago O'Hare Intl
Nov 2
ORD8:55 amChicago O'Hare Intl
8h 47m
2 stops
BRD5:42 pmBrainerd Crow Wing County
$754
Find similar

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 October 14, 2025.
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

BrainerdChicago

BRD - ORD

BRDORD

Brainerd Crow Wing County

Mon 10/27

6:20 pm-9:19 pm

1 stop2h 59m

Chicago O'Hare Intl

Fri 10/31

11:13 am-5:42 pm

1 stop6h 29m

$639

BrainerdChicago

BRD - ORD

BRDORD

Brainerd Crow Wing County

Wed 10/29

6:20 pm-9:19 pm

1 stop2h 59m

Chicago O'Hare Intl

Sun 11/2

5:08 am-9:09 am

1 stop4h 01m

$654

BrainerdChicago

BRD - ORD

BRDORD

Brainerd Crow Wing County

Wed 10/29

6:20 pm-9:19 pm

1 stop2h 59m

Chicago O'Hare Intl

Sun 11/2

8:55 am-5:42 pm

2 stops8h 47m

$754

BrainerdChicago

BRD - ORD

BRDORD

Brainerd Crow Wing County

Mon 10/27

10:55 am-6:14 pm

2 stops7h 19m

Chicago O'Hare Intl

Fri 10/31

11:13 am-5:42 pm

1 stop6h 29m

$779

BrainerdChicago

BRD - MDW

BRDMDW

Brainerd Crow Wing County

Mon 10/27

10:55 am-6:25 pm

2 stops7h 30m

Chicago Midway

Fri 10/31

9:35 am-5:42 pm

2 stops8h 07m

$971

BrainerdChicago

BRD - ORD

BRDORD

Brainerd Crow Wing County

Fri 11/28

6:18 pm-9:36 pm

1 stop3h 18m

$253

BrainerdChicago

BRD - ORD

BRDORD

Brainerd Crow Wing County

Sat 11/8

10:55 am-3:00 pm

1 stop4h 05m

$273

BrainerdChicago

BRD - MDW

BRDMDW

Brainerd Crow Wing County

Sat 11/8

10:55 am-6:25 pm

2 stops7h 30m

$299

BrainerdChicago

BRD - ORD

BRDORD

Brainerd Crow Wing County

Sun 10/19

10:55 am-3:00 pm

1 stop4h 05m

$403

BrainerdChicago

BRD - MDW

BRDMDW

Brainerd Crow Wing County

Mon 10/20

10:55 am-6:25 pm

2 stops7h 30m

$1,171

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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

Direct flights

None
There are no direct flights from Brainerd to Chicago. There are no popular flight routes from Brainerd to Chicago.
Search flight deals

  • 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 2h 59m.

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

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
Thu 11/13
Thu 11/20
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