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$183+ 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 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
MFE — CHI
Aug 22 — Aug 291
Sat 8/22
Sat 8/29
1 adult, Economy
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Cheap 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 July 23, 2026.

This American Airlines deal was found by Cheapflights users on 7/18. 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.
Wed 9/304:17 pm
BRO
-
ORD
1 stop7h 57m
American Airlines
Sat 10/33:00 pm
ORD
-
BRO
1 stop5h 05m
American Airlines
Deal found 7/18$328
This American Airlines deal was found by Cheapflights users on 7/21. 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 9/55:47 am
BRO
-
ORD
1 stop7h 41m
American Airlines
Sun 9/135:00 am
ORD
-
BRO
1 stop5h 09m
American Airlines
Deal found 7/21$329
This American Airlines deal was found by Cheapflights users on 7/22. 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 8/146:37 pm
BRO
-
ORD
1 stop5h 41m
American Airlines
Mon 8/243:54 pm
ORD
-
BRO
1 stop7h 29m
American Airlines
Deal found 7/22$339
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/218:35 am
BRO
-
ORD
2 stops35h 33m
Multiple Airlines
Sun 8/237:44 pm
ORD
-
BRO
1 stop12h 11m
Multiple Airlines
Deal found 7/20$347
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/178:35 am
BRO
-
ORD
1 stop14h 35m
Multiple Airlines
Thu 8/207:44 pm
ORD
-
BRO
1 stop12h 11m
Multiple Airlines
Deal found 7/20$349
This United Airlines deal was found by Cheapflights users on 7/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/34:38 pm
BRO
-
ORD
1 stop6h 48m
United Airlines
Tue 9/86:30 am
ORD
-
BRO
1 stop4h 53m
United Airlines
Deal found 7/18$353
This Kiwi.com deal was found by Cheapflights users on 7/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/288:45 am
BRO
-
ORD
2 stops27h 17m
Multiple Airlines
Thu 10/14:49 pm
ORD
-
BRO
1 stop15h 16m
Multiple Airlines
Deal found 7/18$358
This American Airlines deal was found by Cheapflights users on 7/21. 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.
Fri 8/72:37 pm
BRO
-
ORD
1 stop6h 39m
American Airlines
Fri 8/217:00 am
ORD
-
BRO
1 stop7h 07m
American Airlines
Deal found 7/21$364
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/178:35 am
BRO
-
ORD
1 stop14h 35m
Multiple Airlines
Sun 8/237:05 am
ORD
-
BRO
2 stops24h 50m
Multiple Airlines
Deal found 7/20$372
This United Airlines deal was found by Cheapflights users on 7/22. 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.
Sat 8/812:10 pm
BRO
-
ORD
1 stop5h 19m
United Airlines
Sat 8/156:30 am
ORD
-
BRO
1 stop4h 53m
United Airlines
Deal found 7/22$374
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/178:35 am
BRO
-
ORD
1 stop14h 35m
Multiple Airlines
Tue 8/259:20 pm
ORD
-
BRO
2 stops58h 35m
Multiple Airlines
Deal found 7/20$396

Find 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 July 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$328
(American Airlines)

One-way from

$183
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$384
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 South Padre Island to Chicago (CHI)
Search Deals
One-way flight from South Padre Island to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($42 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals

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 July 23, 2026.
Use the filters below to find and compare flights from South Padre Island to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Wed 11/4

4:38 pm-11:26 pm

1 stop6h 48m

Chicago O'Hare Intl

Sun 11/8

6:00 am-11:16 am

1 stop5h 16m

$329
Quickest round-trip

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Sat 8/8

12:10 pm-5:29 pm

1 stop5h 19m

Chicago O'Hare Intl

Sat 8/15

6:30 am-11:23 am

1 stop4h 53m

$374

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Wed 9/30

4:37 pm-11:27 pm

1 stop6h 50m

Chicago O'Hare Intl

Tue 10/6

5:30 am-11:23 am

1 stop5h 53m

$418

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Mon 9/28

4:37 pm-12:23 am

1 stop7h 46m

Chicago O'Hare Intl

Sat 10/3

4:11 pm-9:50 pm

1 stop5h 39m

$418

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Fri 1/8

5:25 pm-12:15 am

1 stop6h 50m

Chicago O'Hare Intl

Tue 1/12

2:15 pm-9:18 pm

1 stop7h 03m

$419

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Fri 10/2

4:37 pm-11:27 pm

1 stop6h 50m

Chicago O'Hare Intl

Sat 10/3

2:10 pm-9:50 pm

1 stop7h 40m

$453

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Sat 12/12

5:25 pm-12:15 am

1 stop6h 50m

Chicago O'Hare Intl

Thu 12/31

7:41 am-4:01 pm

1 stop8h 20m

$454

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Wed 9/30

12:05 pm-6:30 pm

1 stop6h 25m

Chicago O'Hare Intl

Mon 10/5

6:25 am-6:13 pm

1 stop11h 48m

$463

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Mon 8/10

8:35 am-11:10 pm

1 stop14h 35m

Chicago O'Hare Intl

Fri 8/14

9:13 pm-7:55 am

2 stops58h 42m

$474
Cheapest one-way

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Fri 10/23

8:45 am-1:16 pm

1 stop28h 31m

$183

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/21

Showing 1-10 of 11 resultsSorted by cheapest first
1
2

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

How much does it cost to fly round-trip from South Padre Island to Chicago?

Airfare is below average for this route at the moment.
South Padre Island to Chicago flights typically cost between $366 and $477 in September.
The cheapest round-trip price found within the last 5 days was $328 on American Airlines (Sep 30-Oct 3).

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 July 23, 2026.
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
10,024 reviews

Overall

7.4

Crew

8.1

Boarding

7.7

Food

6.6

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
10,024 reviews
United Airlines
7.4
Good
10,024 reviews

Overall

7.4

Crew

8.1

Boarding

7.7

Food

6.6

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
American Airlines
7.1
Good
11,832 reviews
United Airlines
7.4
Good
10,024 reviews

Overall

7.4

Crew

8.1

Boarding

7.7

Food

6.6

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

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 fly from South Padre Island to Chicago in about 6h 48m. The time it takes to get you to your destination can typically vary by up to . The distance from South Padre Island to Chicago is about 1235 mi.

  • 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.

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
Valparaiso
Hammond
Saint Joseph
Porter

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Alternative routes for South Padre Island to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from South Padre Island to Chicago

Discover the top 2 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 July 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$250Average$435FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$268Average$428FlexibilityNo cancel feeOn-time71%

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