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$165+ Cheap flights from South Padre Island, TX to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/23. Fares are subject to change and may not be available on all flights or dates of travel.
MFE — CHI
Nov 22 — Nov 291
Sat 11/22
Sat 11/29
1 adult, Economy
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Cheap flight deals from South Padre Island to Chicago

Keep the following information in mind while searching for South Padre Island to Chicago flight deals. Data was last updated October 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$319
(United Airlines)

One-way from

$165
(American Airlines)

Popular in

October

Cheapest in

July

Average price

$456
Provider with most accurate pricing for Brownsville South Padre Is. Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Brownsville South Padre Is. Intl-Chicago (CHI) flights.
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From South Padre Island to Chicago (CHI)
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One-way flight from South Padre Island to Chicago (CHI)
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Highest demand for flights based on searches. 1% potential increase in price ($4 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from South Padre Island to Chicago

Cheapest flights from South Padre Island to Chicago
Explore the most affordable flight options available from South Padre Island to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 23, 2025.

This United Airlines deal was found by Cheapflights users on 10/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/512:15 pmBRO - ORD
1 stop7h 41mUnited Airlines
Sun 11/95:04 pmORD - BRO
1 stop6h 32mUnited Airlines
Deal found 10/21$319
This American Airlines deal was found by Cheapflights users on 10/22. 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.
Fri 11/216:11 pmBRO - ORD
1 stop5h 20mAmerican Airlines
Mon 11/247:31 amORD - BRO
1 stop6h 49mAmerican Airlines
Deal found 10/22$423
This American Airlines deal was found by Cheapflights users on 10/22. 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.
Thu 11/66:11 pmBRO - ORD
1 stop5h 20mAmerican Airlines
Mon 11/105:10 pmORD - BRO
1 stop5h 54mAmerican Airlines
Deal found 10/22$434
This United Airlines deal was found by Cheapflights users on 10/22. 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.
Fri 11/215:15 pmBRO - ORD
1 stop7h 00mUnited Airlines
Mon 11/242:20 pmORD - BRO
2 stops21h 08mUnited Airlines
Deal found 10/22$484
This American Airlines deal was found by Cheapflights users on 10/22. 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.
Fri 10/315:38 amBRO - ORD
1 stop5h 21mAmerican Airlines
Mon 11/35:10 pmORD - BRO
1 stop5h 54mAmerican Airlines
Deal found 10/22$499

Cheapflights Fare Finder

 
Customize your flight search to find flights from South Padre Island 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 October 23, 2025.
Use the filters below to find and compare flights from South Padre Island to Chicago that are best for you.

Fly from

South Padre Island

Fly to

Chicago

Route

Depart

Return

Price

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Wed 11/5

12:15 pm-7:56 pm

1 stop7h 41m

Chicago O'Hare Intl

Sun 11/9

5:04 pm-11:36 pm

1 stop6h 32m

$319

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Fri 11/21

6:11 pm-11:31 pm

1 stop5h 20m

Chicago O'Hare Intl

Mon 11/24

7:31 am-2:20 pm

1 stop6h 49m

$423

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Thu 11/6

6:11 pm-11:31 pm

1 stop5h 20m

Chicago O'Hare Intl

Mon 11/10

5:10 pm-11:04 pm

1 stop5h 54m

$434

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Fri 11/21

5:15 pm-12:15 am

1 stop7h 00m

Chicago O'Hare Intl

Mon 11/24

2:20 pm-11:28 am

2 stops21h 08m

$484

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Sun 11/23

6:11 pm-11:31 pm

1 stop5h 20m

$165

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Sun 11/23

5:15 pm-9:44 am

2 stops16h 29m

$246

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Sat 11/29

9:30 pm-2:27 am

1 stop4h 57m

$330

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/22

Best time to book a flight from South Padre Island to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from South Padre Island 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 South Padre Island to Chicago

What is the cheapest month to book a flight from South Padre Island to Chicago?

Currently, December is the cheapest month in which you can book a flight from South Padre Island to Chicago (average of $128). Flying from South Padre Island to Chicago in February is currently the most expensive (average of $328). 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.

What is the cheapest time of day to fly from SO9 to CHI?

Find hourly flight availability from South Padre Island to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 23, 2025.

It’s optimal to fly from South Padre Island to Chicago in the morning. By choosing this option you can save up to 29% on the cost of your flight, compared to a flight at noon.

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 October 23, 2025.
Read reviews from past customers who have flown United Airlines and American Airlines from South Padre Island to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,995 reviews

Entertainment

7.1

Boarding

7.7

Overall

7.4

Comfort

7.3

Food

6.6

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
8,995 reviews
United Airlines
7.4
Good
8,995 reviews

Entertainment

7.1

Boarding

7.7

Overall

7.4

Comfort

7.3

Food

6.6

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
American Airlines
7.2
Good
11,032 reviews
United Airlines
7.4
Good
8,995 reviews

Entertainment

7.1

Boarding

7.7

Overall

7.4

Comfort

7.3

Food

6.6

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

Related info for your journey

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

  • How long is the flight from South Padre Island to Chicago?

    Airlines like United Airlines and American Airlines fly from South Padre Island to Chicago in about 5h 20m. The time it takes to get you to your destination can typically vary by up to 2h 21m. The distance from South Padre Island to Chicago is about 1235 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • Can I find deals for flights from South Padre Island to Chicago that include hotel bookings?

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

  • How can I find direct flights from South Padre Island to Chicago?

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

  • Can I find deals for business class flights from South Padre Island to Chicago?

    Yes. Cheapflights offers flight deals from South Padre Island 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 South Padre Island to Chicago?

    Currently, December is the cheapest month in which you can book a flight from South Padre Island to Chicago (average of $128). Flying from South Padre Island to Chicago in February is currently the most expensive (average of $328). 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
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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Top 3 airlines flying from South Padre Island to Chicago

Discover the top 3 airlines that operate flights from South Padre Island 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 October 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$159Average$365FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$252Average$319FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$268Average$404FlexibilityNo cancel feeOn-time69%

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