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Cheap flight deals from Brainerd to Chicago Starting at $341

Discover our range of affordable one-way and round-trip flights from Brainerd to Chicago and kick-start your next adventure today!

  • Round-trip
      • BRD06:20 pm
        21h 10m
        1 stop
        ORD03:30 pm
        Tue, Jan 21|Brainerd - Chicago|Delta Air Lines
        ORD06:59 pm
        22h 46m
        1 stop
        BRD05:45 pm
        Mon, Jan 27|Chicago - Brainerd|Delta Air Lines
        $341$443
        23% OFF
        23% OFF
        $443$341

        Choose Delta Air Lines flights from Brainerd to Chicago. The one-way connecting flight with Delta Air Lines departs from Brainerd Lakes Regional Airport on Tue, Jan 21-Mon, Jan 27, arriving at O'Hare International Airport. One-way Prices start from $341 including taxes and charges.

      • BRD10:45 am
        7h 2m
        1 stop
        MDW05:47 pm
        Thu, Jan 23|Brainerd - Chicago|Delta Air Lines
        MDW10:19 am
        7h 26m
        1 stop
        BRD05:45 pm
        Wed, Jan 29|Chicago - Brainerd|Delta Air Lines
        $348$443
        22% OFF
        22% OFF
        $443$348

        Choose Delta Air Lines flights from Brainerd to Chicago. The one-way connecting flight with Delta Air Lines departs from Brainerd Lakes Regional Airport on Thu, Jan 23-Wed, Jan 29, arriving at Midway International Airport. One-way Prices start from $348 including taxes and charges.

      • BRD06:20 pm
        23h 27m
        1 stop
        MDW05:47 pm
        Tue, Jan 28|Brainerd - Chicago|Delta Air Lines
        MDW10:19 am
        7h 26m
        1 stop
        BRD05:45 pm
        Mon, Feb 3|Chicago - Brainerd|Delta Air Lines
        $348$443
        21% OFF
        21% OFF
        $443$348

        Choose Delta Air Lines flights from Brainerd to Chicago. The one-way connecting flight with Delta Air Lines departs from Brainerd Lakes Regional Airport on Tue, Jan 28-Mon, Feb 3, arriving at Midway International Airport. One-way Prices start from $348 including taxes and charges.

      • BRD10:45 am
        6h 44m
        1 stop
        ORD05:29 pm
        Thu, Jan 30|Brainerd - Chicago|Delta Air Lines
        MDW10:19 am
        7h 26m
        1 stop
        BRD05:45 pm
        Wed, Feb 5|Chicago - Brainerd|Delta Air Lines
        $348
        $348

        Choose Delta Air Lines flights from Brainerd to Chicago. The one-way connecting flight with Delta Air Lines departs from Brainerd Lakes Regional Airport on Thu, Jan 30-Wed, Feb 5, arriving at O'Hare International Airport. One-way Prices start from $348 including taxes and charges.

      • BRD06:20 pm
        18h 26m
        1 stop
        MDW12:46 pm
        Tue, Jan 14|Brainerd - Chicago|Delta Air Lines
        MDW11:19 am
        22h 48m
        1 stop
        BRD10:07 am
        Sat, Jan 18|Chicago - Brainerd|Delta Air Lines
        $349
        $349

        Choose Delta Air Lines flights from Brainerd to Chicago. The one-way connecting flight with Delta Air Lines departs from Brainerd Lakes Regional Airport on Tue, Jan 14-Sat, Jan 18, arriving at Midway International Airport. One-way Prices start from $349 including taxes and charges.

      • BRD06:20 pm
        3h 38m
        1 stop
        ORD09:58 pm
        Wed, Jan 15|Brainerd - Chicago|Delta Air Lines
        ORD12:15 pm
        5h 30m
        1 stop
        BRD05:45 pm
        Tue, Jan 21|Chicago - Brainerd|Delta Air Lines
        $352
        $352

        Choose Delta Air Lines flights from Brainerd to Chicago. The one-way connecting flight with Delta Air Lines departs from Brainerd Lakes Regional Airport on Wed, Jan 15-Tue, Jan 21, arriving at O'Hare International Airport. One-way Prices start from $352 including taxes and charges.

      • BRD06:20 pm
        15h 19m
        1 stop
        MDW09:39 am
        Sun, Jan 12|Brainerd - Chicago|Delta Air Lines
        ORD06:59 pm
        15h 8m
        1 stop
        BRD10:07 am
        Sat, Jan 18|Chicago - Brainerd|Delta Air Lines
        $353
        $353

        Choose Delta Air Lines flights from Brainerd to Chicago. The one-way connecting flight with Delta Air Lines departs from Brainerd Lakes Regional Airport on Sun, Jan 12-Sat, Jan 18, arriving at Midway International Airport. One-way Prices start from $353 including taxes and charges.

      • BRD06:20 pm
        3h 38m
        1 stop
        ORD09:58 pm
        Wed, Jan 29|Brainerd - Chicago|Delta Air Lines
        MDW01:26 pm
        4h 19m
        1 stop
        BRD05:45 pm
        Tue, Feb 4|Chicago - Brainerd|Delta Air Lines
        $359
        $359

        Choose Delta Air Lines flights from Brainerd to Chicago. The one-way connecting flight with Delta Air Lines departs from Brainerd Lakes Regional Airport on Wed, Jan 29-Tue, Feb 4, arriving at O'Hare International Airport. One-way Prices start from $359 including taxes and charges.

      • BRD06:20 pm
        3h 38m
        1 stop
        ORD09:58 pm
        Wed, Feb 5|Brainerd - Chicago|Delta Air Lines
        MDW01:26 pm
        4h 19m
        1 stop
        BRD05:45 pm
        Tue, Feb 11|Chicago - Brainerd|Delta Air Lines
        $364
        $364

        Choose Delta Air Lines flights from Brainerd to Chicago. The one-way connecting flight with Delta Air Lines departs from Brainerd Lakes Regional Airport on Wed, Feb 5-Tue, Feb 11, arriving at O'Hare International Airport. One-way Prices start from $364 including taxes and charges.

      • BRD06:20 pm
        3h 38m
        1 stop
        ORD09:58 pm
        Sat, Jan 11|Brainerd - Chicago|Delta Air Lines
        MDW01:26 pm
        4h 19m
        1 stop
        BRD05:45 pm
        Fri, Jan 17|Chicago - Brainerd|Delta Air Lines
        $367
        $367

        Choose Delta Air Lines flights from Brainerd to Chicago. The one-way connecting flight with Delta Air Lines departs from Brainerd Lakes Regional Airport on Sat, Jan 11-Fri, Jan 17, arriving at O'Hare International Airport. One-way Prices start from $367 including taxes and charges.

      • BRD01:00 pm
        3h 5m
        Nonstop
        CHI02:00 pm
        Wed, Jan 15|Brainerd - Chicago|Delta Air Lines
        Find More Flights
        Find More Flights

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

When is the cheapest time to fly from Brainerd to Chicago?

Price trend charts are a great way of tracking how much your flights cost in the lead up to departure and can help you choose when to book your tickets. See how prices to Chicago from Brainerd have changed and are set to move below.

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Alternative Cheap Routes from Brainerd to Chicago

Did you know that you can save money and time on an alternative route from Brainerd to Chicago? Check out some of the different available routes below.

  • Cheapest
    Delta Air Lines
    BRD
    06:20 pm
    21h 10m
    2 transfer
    ORD
    03:30 pm
    Brainerd Lakes Regional Airport - O'Hare International Airport
    Tue, Jan 21Delta Air Lines
    $341
  • Delta Air Lines
    BRD
    06:20 pm
    18h 26m
    2 transfer
    MDW
    12:46 pm
    Brainerd Lakes Regional Airport - Midway International Airport
    Tue, Jan 21Delta Air Lines
    $341
  • Delta Air Lines
    BRD
    06:20 pm
    18h 26m
    2 transfer
    MDW
    12:46 pm
    Brainerd Lakes Regional Airport - Midway International Airport
    Tue, Jan 21Delta Air Lines
    $341
    Find More Flights

Frequently Asked Questions

  • When are flight tickets from Brainerd (BRD) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from Brainerd to Chicago based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much do flights from Brainerd (BRD) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around $383.

  • What is the transportation method from the main airport to downtown in Chicago?

    • The distance from O'Hare International Airport to downtown is about 25 km. It takes about 40 minutes by taxi.
    • The distance from Midway International Airport to downtown is about 14 km. It takes about 30 minutes by taxi.

How to find a cheap flight from Brainerd to Chicago

If you don’t know some of the key things to look out for when buying flight tickets, prices can often end up sky high or, worse, sold out! We’ve carefully compiled our six most important steps to help ensure you’re getting the best deals when planning your next journey.
1
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com

Flight Info | Brainerd to Chicago

Off-season for travelNovember
Peak season for travelDecember
Flight distance721.92 km
Popular airlineDelta Air Lines

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