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Cheap flights from Brainerd to Chicago from $290

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Brainerd to Chicago departing on 10/3. 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 - 4:59 pmBRD  Brainerd Crow Wing County-ORD Chicago O'Hare Intl
6h 04m1 stop Minneapolis St Paul
Delta Logo
6:10 am - 10:16 amORD  Chicago O'Hare Intl-BRD Brainerd Crow Wing County
4h 06m1 stop Minneapolis St Paul
$290Delta
Sat, Oct 3 - Mon, Oct 5
Delta Logo
6:45 am - 12:58 pmBRD  Brainerd Crow Wing County-ORD Chicago O'Hare Intl
6h 13m2 stops Minneapolis St Paul Detroit Metropolitan Wayne County
Delta Logo
6:10 am - 10:16 amORD  Chicago O'Hare Intl-BRD Brainerd Crow Wing County
4h 06m1 stop Minneapolis St Paul
$300Delta
Sat, Oct 3 - Mon, Oct 5
Delta Logo
10:55 am - 4:59 pmBRD  Brainerd Crow Wing County-ORD Chicago O'Hare Intl
6h 04m1 stop Minneapolis St Paul
Delta Logo
6:10 am - 10:16 amORD  Chicago O'Hare Intl-BRD Brainerd Crow Wing County
4h 06m1 stop Minneapolis St Paul
$325Delta
Sat, Oct 3 - Mon, Oct 5
Delta Logo
10:55 am - 2:29 pmBRD  Brainerd Crow Wing County-ORD Chicago O'Hare Intl
3h 34m1 stop Minneapolis St Paul
Delta Logo
6:10 am - 10:16 amORD  Chicago O'Hare Intl-BRD Brainerd Crow Wing County
4h 06m1 stop Minneapolis St Paul
$332Delta
Sat, Oct 3 - Mon, Oct 5
Delta Logo
6:45 am - 12:58 pmBRD  Brainerd Crow Wing County-ORD Chicago O'Hare Intl
6h 13m2 stops Minneapolis St Paul Detroit Metropolitan Wayne County
Delta Logo
6:10 am - 10:16 amORD  Chicago O'Hare Intl-BRD Brainerd Crow Wing County
4h 06m1 stop Minneapolis St Paul
$335Delta
Sat, Oct 3 - Mon, Oct 5
Delta Logo
6:45 am - 12:58 pmBRD  Brainerd Crow Wing County-ORD Chicago O'Hare Intl
6h 13m2 stops Minneapolis St Paul Detroit Metropolitan Wayne County
Delta Logo
6:10 am - 10:16 amORD  Chicago O'Hare Intl-BRD Brainerd Crow Wing County
4h 06m1 stop Minneapolis St Paul
$342Delta
Sat, Oct 3 - Mon, Oct 5
Delta Logo
6:45 am - 1:08 pmBRD  Brainerd Crow Wing County-ORD Chicago O'Hare Intl
6h 23m2 stops Minneapolis St Paul Detroit Metropolitan Wayne County
Delta Logo
6:00 am - 10:14 amORD  Chicago O'Hare Intl-BRD Brainerd Crow Wing County
4h 14m1 stop Minneapolis St Paul
$491Delta
Tue, Sep 1 - Mon, Sep 7
Delta Logo
6:45 am - 12:39 pmBRD  Brainerd Crow Wing County-MDW Chicago Midway
5h 54m2 stops Minneapolis St Paul Detroit Metropolitan Wayne County
Delta Logo
1:19 pm - 8:47 pmMDW  Chicago Midway-BRD Brainerd Crow Wing County
7h 28m2 stops Detroit Metropolitan Wayne County Minneapolis St Paul
$591Delta
Sat, Oct 3 - Mon, Oct 5
Delta Logo
6:45 am - 12:39 pmBRD  Brainerd Crow Wing County-MDW Chicago Midway
5h 54m2 stops Minneapolis St Paul Detroit Metropolitan Wayne County
Delta Logo
1:19 pm - 8:47 pmMDW  Chicago Midway-BRD Brainerd Crow Wing County
7h 28m2 stops Detroit Metropolitan Wayne County Minneapolis St Paul
$599Delta
Sat, Oct 3 - Mon, Oct 5
Delta Logo
6:45 am - 12:39 pmBRD  Brainerd Crow Wing County-MDW Chicago Midway
5h 54m2 stops Minneapolis St Paul Detroit Metropolitan Wayne County
Delta Logo
1:19 pm - 8:47 pmMDW  Chicago Midway-BRD Brainerd Crow Wing County
7h 28m2 stops Detroit Metropolitan Wayne County Minneapolis St Paul
$683Delta
Sat, Oct 3 - Mon, Oct 5

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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
6h 04m
1 stop
ORD4:59 pmChicago O'Hare Intl
Oct 5
ORD6:10 amChicago O'Hare Intl
4h 06m
1 stop
BRD10:16 amBrainerd Crow Wing County
$290
Delta
Oct 3
BRD6:45 amBrainerd Crow Wing County
6h 13m
2 stops
ORD12:58 pmChicago O'Hare Intl
Oct 5
ORD6:10 amChicago O'Hare Intl
4h 06m
1 stop
BRD10:16 amBrainerd Crow Wing County
$300
Delta
Oct 3
BRD10:55 amBrainerd Crow Wing County
6h 04m
1 stop
ORD4:59 pmChicago O'Hare Intl
Oct 5
ORD6:10 amChicago O'Hare Intl
4h 06m
1 stop
BRD10:16 amBrainerd Crow Wing County
$325

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 August 13, 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 Brainerd Crow Wing County - ORD Chicago O'Hare Intl

BRDORD

Brainerd Crow Wing County

Sat 10/3

10:55 am-4:59 pm

1 stop6h 04m

Chicago O'Hare Intl

Mon 10/5

6:10 am-10:16 am

1 stop4h 06m

$290

BrainerdChicago

BRD Brainerd Crow Wing County - ORD Chicago O'Hare Intl

BRDORD

Brainerd Crow Wing County

Sat 10/3

6:45 am-12:58 pm

2 stops6h 13m

Chicago O'Hare Intl

Mon 10/5

6:10 am-10:16 am

1 stop4h 06m

$300

BrainerdChicago

BRD Brainerd Crow Wing County - ORD Chicago O'Hare Intl

BRDORD

Brainerd Crow Wing County

Sat 10/3

10:55 am-4:59 pm

1 stop6h 04m

Chicago O'Hare Intl

Mon 10/5

6:10 am-10:16 am

1 stop4h 06m

$325
Quickest round-trip

BrainerdChicago

BRD Brainerd Crow Wing County - ORD Chicago O'Hare Intl

BRDORD

Brainerd Crow Wing County

Sat 10/3

10:55 am-2:29 pm

1 stop3h 34m

Chicago O'Hare Intl

Mon 10/5

6:10 am-10:16 am

1 stop4h 06m

$332

BrainerdChicago

BRD Brainerd Crow Wing County - ORD Chicago O'Hare Intl

BRDORD

Brainerd Crow Wing County

Sat 10/3

6:45 am-12:58 pm

2 stops6h 13m

Chicago O'Hare Intl

Mon 10/5

6:10 am-10:16 am

1 stop4h 06m

$335

BrainerdChicago

BRD Brainerd Crow Wing County - ORD Chicago O'Hare Intl

BRDORD

Brainerd Crow Wing County

Sat 10/3

6:45 am-12:58 pm

2 stops6h 13m

Chicago O'Hare Intl

Mon 10/5

6:10 am-10:16 am

1 stop4h 06m

$342

BrainerdChicago

BRD Brainerd Crow Wing County - ORD Chicago O'Hare Intl

BRDORD

Brainerd Crow Wing County

Tue 9/1

6:45 am-1:08 pm

2 stops6h 23m

Chicago O'Hare Intl

Mon 9/7

6:00 am-10:14 am

1 stop4h 14m

$491

BrainerdChicago

BRD Brainerd Crow Wing County - MDW Chicago Midway

BRDMDW

Brainerd Crow Wing County

Sat 10/3

6:45 am-12:39 pm

2 stops5h 54m

Chicago Midway

Mon 10/5

1:19 pm-8:47 pm

2 stops7h 28m

$591

BrainerdChicago

BRD Brainerd Crow Wing County - MDW Chicago Midway

BRDMDW

Brainerd Crow Wing County

Sat 10/3

6:45 am-12:39 pm

2 stops5h 54m

Chicago Midway

Mon 10/5

1:19 pm-8:47 pm

2 stops7h 28m

$599

BrainerdChicago

BRD Brainerd Crow Wing County - MDW Chicago Midway

BRDMDW

Brainerd Crow Wing County

Sat 10/3

6:45 am-12:39 pm

2 stops5h 54m

Chicago Midway

Mon 10/5

1:19 pm-8:47 pm

2 stops7h 28m

$683

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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.
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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.

Frequently asked questions about flying from Brainerd to Chicago

  • How do I get Price Alerts for flights from Brainerd to Chicago?

    Search flight deals from Brainerd to Chicago. While viewing offers you’ll have the option to create a Price Alert.

  • How can I save money on flights from Brainerd to Chicago with momondo?

    Plan your trips smart with the “Price Forecast” feature, which uses flight data to help you pick the best days to fly for the lowest fares. Our “Price Calendar” helps you get the most for your money by showing you when it’s most advantageous to fly. Curate your own travel experiences for less with “Explore”. Expert travel hacks to fuel your next adventure are a click away with “Discover” by momondo. Set up our “Price Alerts” to track fare changes and book when prices are at their lowest point.

  • How does momondo find its flight prices?

    We aggregate our prices from over 700+ competitors from airlines to OTAs. We operate in over 30 markets worldwide to show you a wide range of travel options.

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
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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