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$329+ Cheap flights from Brownsville (BRO) to Chicago (CHI)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/16. Fares are subject to change and may not be available on all flights or dates of travel.
BRO — CHI
Jun 22 — Jun 291
Mon 6/22
Mon 6/29
1 adult, Economy
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Cheap flight deals from Brownsville to Chicago

Cheapest flights from Brownsville to Chicago
Explore the most affordable flight options available from Brownsville to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 23, 2026.

This American Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/166:42 pm
BRO
-
ORD
1 stop5h 57m
American Airlines
Tue 6/305:00 am
ORD
-
BRO
1 stop5h 14m
American Airlines
Deal found 5/18$329
This American Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:37 pm
BRO
-
ORD
1 stop5h 21m
American Airlines
Thu 9/1010:35 am
ORD
-
BRO
1 stop7h 38m
American Airlines
Deal found 5/19$330
This American Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/226:42 pm
BRO
-
ORD
1 stop5h 57m
American Airlines
Mon 6/295:00 am
ORD
-
BRO
1 stop5h 14m
American Airlines
Deal found 5/20$395
This Kiwi.com deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/318:35 am
BRO
-
ORD
2 stops36h 18m
Multiple Airlines
Thu 9/109:26 am
ORD
-
BRO
1 stop22h 39m
Multiple Airlines
Deal found 5/19$396
This American Airlines deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/66:42 pm
BRO
-
ORD
1 stop5h 57m
American Airlines
Wed 6/105:00 am
ORD
-
BRO
1 stop5h 14m
American Airlines
Deal found 5/22$399
This American Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/306:42 pm
BRO
-
ORD
1 stop6h 00m
American Airlines
Wed 6/36:00 am
ORD
-
BRO
1 stop8h 17m
American Airlines
Deal found 5/18$417
This American Airlines deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/236:42 pm
BRO
-
ORD
1 stop6h 00m
American Airlines
Tue 5/2611:50 am
ORD
-
BRO
1 stop6h 22m
American Airlines
Deal found 5/21$441
This United Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/224:44 pm
BRO
-
ORD
1 stop8h 01m
United Airlines
Mon 6/296:30 am
ORD
-
BRO
1 stop4h 56m
United Airlines
Deal found 5/19$443
This United Airlines deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/205:10 am
BRO
-
ORD
1 stop6h 17m
United Airlines
Thu 12/3111:30 am
ORD
-
BRO
1 stop7h 58m
United Airlines
Deal found 5/22$454
This American Airlines deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/146:42 pm
BRO
-
ORD
1 stop5h 57m
American Airlines
Sun 6/215:00 am
ORD
-
BRO
1 stop5h 14m
American Airlines
Deal found 5/17$464

Find flight deals from Brownsville to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Brownsville (BRO) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$329
(American Airlines)

Popular in

December

Cheapest in

July

Average price

$369
Provider with most accurate pricing for Brownsville South Padre Is. Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Brownsville South Padre Is. Intl-Chicago (CHI) flights.
Search Deals
From Brownsville South Padre Is. Intl to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($72 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Brownsville 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, Cheapflights users made 2,558,603 searches. Data last updated May 23, 2026.
Use the filters below to find and compare flights from Brownsville to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Sat 6/27

6:42 pm-12:39 am

1 stop5h 57m

Chicago O'Hare Intl

Thu 7/2

5:00 am-10:05 am

1 stop5h 05m

$395

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Sun 6/14

6:42 pm-12:39 am

1 stop5h 57m

Chicago O'Hare Intl

Sun 6/21

5:00 am-10:14 am

1 stop5h 14m

$464

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Mon 6/15

6:42 pm-12:39 am

1 stop5h 57m

Chicago O'Hare Intl

Sun 6/21

5:00 am-10:14 am

1 stop5h 14m

$465

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Thu 6/18

6:42 pm-12:39 am

1 stop5h 57m

Chicago O'Hare Intl

Wed 6/24

5:00 am-10:14 am

1 stop5h 14m

$484

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Sat 6/6

4:44 pm-11:15 pm

1 stop6h 31m

Chicago O'Hare Intl

Wed 6/10

12:40 pm-6:37 pm

1 stop5h 57m

$489

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Thu 9/3

12:05 pm-6:28 am

2 stops18h 23m

Chicago O'Hare Intl

Tue 9/8

6:30 am-11:23 am

1 stop4h 53m

$538

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Tue 8/4

12:10 pm-8:05 pm

1 stop7h 55m

Chicago O'Hare Intl

Fri 8/7

9:40 pm-3:57 pm

1 stop18h 17m

$548

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Thu 8/20

4:38 pm-11:26 pm

1 stop6h 48m

Chicago O'Hare Intl

Mon 8/24

10:40 am-6:13 pm

1 stop7h 33m

$554

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Sat 6/27

4:44 pm-12:45 am

1 stop8h 01m

Chicago O'Hare Intl

Thu 7/2

9:25 pm-11:26 am

2 stops14h 01m

$597

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Mon 6/22

4:44 pm-12:45 am

1 stop8h 01m

Chicago O'Hare Intl

Mon 6/29

7:05 am-6:37 pm

2 stops11h 32m

$663

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/21

Showing 1-10 of 15 resultsSorted by cheapest first
1
2

Compare providers for flights from Brownsville to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Brownsville to Chicago in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Brownsville-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Brownsville-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Brownsville-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Brownsville-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Brownsville-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Brownsville to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Brownsville with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Brownsville to Chicago

What is the cheapest month to book a flight from Brownsville to Chicago?

Currently, September is the cheapest month in which you can book a flight from Brownsville to Chicago (average of $210). Flying from Brownsville to Chicago in March is currently the most expensive (average of $463). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

How much does it cost to fly round-trip from Brownsville to Chicago?

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated May 23, 2026.
Get a feel of what it's like to fly with United Airlines and American Airlines from Brownsville to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,751 reviews

Crew

8.1

Entertainment

7.1

Food

6.6

Overall

7.4

Boarding

7.7

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.
United Airlines
7.4
Good
9,751 reviews
United Airlines
7.4
Good
9,751 reviews

Crew

8.1

Entertainment

7.1

Food

6.6

Overall

7.4

Boarding

7.7

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.
American Airlines
7.1
Good
11,644 reviews
United Airlines
7.4
Good
9,751 reviews

Crew

8.1

Entertainment

7.1

Food

6.6

Overall

7.4

Boarding

7.7

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.

Related info for your journey

Find useful and relevant information for your journey from Brownsville to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Brownsville to Chicago?

    If you book a flight to Chicago from Brownsville, you will be flying from South Padre Is. Intl, which is the city’s only airport. Brownsville South Padre Is. Intl (BRO) is located 4.5 mi from the center of Brownsville. There are 0 flights from South Padre Is. Intl to Chicago per day from 1 airline.

  • How long is the flight from Brownsville to Chicago?

    There are many flights that can get you from Brownsville to Chicago in 5h 57m. Fly via American Airlines or United Airlines to get the fastest option. Brownsville and Chicago are separated by a distance of 1235 mi. This flight may include one or multiple stops.

  • What is the cheapest airline to fly from Brownsville to Chicago round-trip?

    Our cheapest airline available from Brownsville to Chicago is American Airlines. Our recent data shows that you can find tickets from as low as $293 on this airline. Users have found that American Airlines is 29% cheaper than the other options available to this destination.

  • Can I find deals for flights from Brownsville to Chicago that include hotel bookings?

    Yes. In addition to deals on Brownsville to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Brownsville to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Brownsville to Chicago.

  • Can I find deals for business class flights from Brownsville to Chicago?

    Yes. Cheapflights offers flight deals from Brownsville to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Brownsville to Chicago?

    Currently, September is the cheapest month in which you can book a flight from Brownsville to Chicago (average of $210). Flying from Brownsville to Chicago in March is currently the most expensive (average of $463). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Brownsville to Chicago

Discover the top airline that operate flights from Brownsville to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$293Average$444FlexibilityNo cancel feeOn-time71%

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