Cheap Flights from Brainerd (BRD) to Chicago (MDW)

Popular airlines from Brainerd, MN (BRD-Brainerd Lakes Regional) to Chicago Midway Airport (MDW)

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Cheap Flights from Brainerd to Chicago (BRD-MDW)

Prices were available within the past 7 days and start at for one-way flights and $416 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Mon, Sep 29 - Tue, Sep 30
BRD
Brainerd
MDW
Chicago
$416 Roundtrip, found 6 days ago
$416
Roundtrip
found 6 days ago
Select Delta flight, departing Mon, Sep 29 from Brainerd to Chicago, returning Tue, Sep 30, priced at $416 found 6 days ago
Delta
Fri, Sep 26 - Sun, Sep 28
BRD
Brainerd
MDW
Chicago
$590 Roundtrip, found 6 days ago
$590
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Sep 26 from Brainerd to Chicago, returning Sun, Sep 28, priced at $590 found 6 days ago
Delta
Thu, Sep 18 - Sun, Sep 21
BRD
Brainerd
MDW
Chicago
$632 Roundtrip, found 4 days ago
$632
Roundtrip
found 4 days ago
Select Delta flight, departing Thu, Sep 18 from Brainerd to Chicago, returning Sun, Sep 21, priced at $632 found 4 days ago
Delta
Thu, Sep 18 - Sun, Sep 21
BRD
Brainerd
MDW
Chicago
$742 Roundtrip, found 4 days ago
$742
Roundtrip
found 4 days ago
Select Delta flight, departing Thu, Sep 18 from Brainerd to Chicago, returning Sun, Sep 21, priced at $742 found 4 days ago
Delta
Fri, Sep 12 - Sun, Sep 14
BRD
Brainerd
MDW
Chicago
$968 Roundtrip, found 1 day ago
$968
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Sep 12 from Brainerd to Chicago, returning Sun, Sep 14, priced at $968 found 1 day ago
Delta
Fri, Sep 26 - Sun, Sep 28
BRD
Brainerd
MDW
Chicago
$2,310 Roundtrip, found 6 days ago
$2,310
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Sep 26 from Brainerd to Chicago, returning Sun, Sep 28, priced at $2,310 found 6 days ago
Delta
Thu, Sep 18 - Sun, Sep 21
BRD
Brainerd
MDW
Chicago
$2,362 Roundtrip, found 4 days ago
$2,362
Roundtrip
found 4 days ago
Select Delta flight, departing Thu, Sep 18 from Brainerd to Chicago, returning Sun, Sep 21, priced at $2,362 found 4 days ago
Delta
Thu, Sep 18 - Sun, Sep 21
BRD
Brainerd
MDW
Chicago
$2,492 Roundtrip, found 4 days ago
$2,492
Roundtrip
found 4 days ago
Select Delta flight, departing Thu, Sep 18 from Brainerd to Chicago, returning Sun, Sep 21, priced at $2,492 found 4 days ago
Delta
Fri, Sep 12 - Sun, Sep 14
BRD
Brainerd
MDW
Chicago
$2,638 Roundtrip, found 1 day ago
$2,638
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Sep 12 from Brainerd to Chicago, returning Sun, Sep 14, priced at $2,638 found 1 day ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $334
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $334
Flights from Brainerd (BRD) to Chicago (MDW)
Origin airport
Brainerd Lakes Regional
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
$415
Distance
449 mi

Brainerd to Chicago Flights

The cheapest times to fly from Brainerd to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Brainerd to Chicago are during the month of September. You can find some of the cheapest flights from Brainerd to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Brainerd to Chicago

Sunday is one of the best days to book for cheap flights from Brainerd to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Brainerd to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Brainerd to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Brainerd to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Brainerd to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Brainerd Lakes Regional Airport (BRD) to Midway Intl. Airport (MDW) cost?
Grab a cheap one-way flight or cheap return flight from $416 from Brainerd Lakes Regional Airport (BRD) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Brainerd Lakes Regional Airport (BRD) to Midway Intl. Airport (MDW)?
Traveling in September can help you save, as it's the cheapest month for flights between BRD and MDW. You'll typically find the lowest prices during the off-season.
What is the cheapest airline that flies from Brainerd Lakes Regional Airport (BRD) to Midway Intl. Airport (MDW)?
Use the filters on Expedia to compare different airlines and find the most affordable carrier that'll fly you from BRD to MDW. Then, sort your results by "Price (lowest to highest)" to score the best deal available.
How many flights per day from Brainerd Lakes Regional Airport (BRD) to Midway Intl. Airport (MDW)?
Direct flights from Brainerd Lakes Regional Airport (BRD) to Midway Intl. Airport (MDW) aren't available daily, so you'll need to take a flight with a layover. Explore your options with our filter tool. Enter your travel details and click on either "1 Stop" or "2+ Stops."
What day of the week has the most flights from BRD to MDW?
Usually you'll find the greatest selection of flight options on a Friday. Tuesdays are often the quietest.* However, this can change depending on the time of year, carrier and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Brainerd Lakes Regional Airport (BRD) to Midway Intl. Airport (MDW)?
Select a flight from Brainerd Lakes Regional Airport (BRD) to Midway Intl. Airport (MDW) that takes off before 3 PM to reduce the risk of cancellations. Departures later than this have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Brainerd Lakes Regional Airport (BRD) to Midway Intl. Airport (MDW) last-minute?
Last-minute fares from BRD to MDW are typically more expensive. For the lowest prices, start looking for flights ahead of time. That said, if you're flexible with your travel plans, it's possible to land a cheap fare right before you leave.
Is it cheaper to book a BRD to MDW flight and hotel package?
Opting for a BRD to MDW flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip all in one place. Choose from our impressive range of stays and then add activities, car rentals and flights to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Brainerd Lakes Regional Airport (BRD) to Midway Intl. Airport (MDW)?
If you booked your BRD to MDW flight in the last 24 hours, you may be able to cancel or modify it without any fees. Depending on the airline and the ticket type you purchased, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal for further details.

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*Available to One Key members.