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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 4/9. Fares are subject to change and may not be available on all flights or dates of travel.
MFE — CHI
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

This American Airlines deal was found by Cheapflights users on 1/28. 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 2/128:04 pm
BRO
-
ORD
1 stop4h 51m
American Airlines
Mon 2/165:00 am
ORD
-
BRO
1 stop5h 17m
American Airlines
Deal found 1/28$339
This United Airlines deal was found by Cheapflights users on 1/28. 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 6/195:25 pm
BRO
-
ORD
1 stop7h 20m
United Airlines
Fri 6/269:25 am
ORD
-
BRO
1 stop6h 13m
United Airlines
Deal found 1/28$374
This United Airlines deal was found by Cheapflights users on 1/26. 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.
Tue 2/2412:15 pm
BRO
-
ORD
1 stop7h 38m
United Airlines
Sat 2/2812:45 pm
ORD
-
BRO
1 stop5h 17m
United Airlines
Deal found 1/26$424
This American Airlines deal was found by Cheapflights users on 1/28. 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 1/3010:53 am
BRO
-
ORD
1 stop4h 44m
American Airlines
Sun 2/86:54 am
ORD
-
BRO
1 stop7h 54m
American Airlines
Deal found 1/28$439
This United Airlines deal was found by Cheapflights users on 1/27. 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.
Tue 2/35:25 pm
BRO
-
ORD
1 stop5h 34m
United Airlines
Sat 2/710:35 am
ORD
-
BRO
1 stop7h 27m
United Airlines
Deal found 1/27$489
This United Airlines deal was found by Cheapflights users on 1/28. 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 5/225:25 pm
BRO
-
ORD
1 stop7h 20m
United Airlines
Mon 5/256:30 am
ORD
-
BRO
1 stop4h 52m
United Airlines
Deal found 1/28$501
This United Airlines deal was found by Cheapflights users on 1/28. 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 5/2212:07 pm
BRO
-
ORD
1 stop19h 53m
United Airlines
Sun 5/245:30 am
ORD
-
BRO
1 stop5h 52m
United Airlines
Deal found 1/28$507
This United Airlines deal was found by Cheapflights users on 1/28. 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 2/125:14 pm
BRO
-
ORD
1 stop5h 50m
United Airlines
Mon 2/165:45 am
ORD
-
BRO
1 stop5h 51m
United Airlines
Deal found 1/28$509
This American Airlines deal was found by Cheapflights users on 1/28. 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 5/152:51 pm
BRO
-
ORD
1 stop7h 43m
American Airlines
Sun 5/176:57 am
ORD
-
BRO
1 stop7h 24m
American Airlines
Deal found 1/28$514

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$339
(American Airlines)

One-way from

$165
(United Airlines)

Popular in

December

Cheapest in

July

Average price

$568
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. 19% potential increase in price ($99 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 January 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 January 29, 2026.
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

Sat 2/14

2:58 pm-8:40 pm

1 stop5h 42m

Chicago O'Hare Intl

Mon 2/16

10:49 am-6:14 pm

1 stop7h 25m

$339

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Thu 2/12

8:04 pm-12:55 am

1 stop4h 51m

Chicago O'Hare Intl

Mon 2/16

5:00 am-10:17 am

1 stop5h 17m

$339

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Fri 6/19

5:25 pm-12:45 am

1 stop7h 20m

Chicago O'Hare Intl

Fri 6/26

9:25 am-3:38 pm

1 stop6h 13m

$374

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Tue 2/24

12:15 pm-7:53 pm

1 stop7h 38m

Chicago O'Hare Intl

Sat 2/28

12:45 pm-6:02 pm

1 stop5h 17m

$424

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Fri 5/22

5:25 pm-12:45 am

1 stop7h 20m

Chicago O'Hare Intl

Mon 5/25

6:30 am-11:22 am

1 stop4h 52m

$501

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Fri 5/22

12:07 pm-8:00 am

1 stop19h 53m

Chicago O'Hare Intl

Sun 5/24

5:30 am-11:22 am

1 stop5h 52m

$507

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Thu 2/12

5:14 pm-11:04 pm

1 stop5h 50m

Chicago O'Hare Intl

Mon 2/16

5:45 am-11:36 am

1 stop5h 51m

$509

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Thu 4/9

7:15 am-12:57 pm

1 stop5h 42m

$165

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Tue 4/14

2:51 pm-10:34 pm

1 stop7h 43m

$169

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Wed 3/11

5:15 am-10:07 am

1 stop4h 52m

$205

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 16 results
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

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 $136). 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.

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 January 29, 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
9,215 reviews

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

Crew

8.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
United Airlines
7.4
Good
9,215 reviews
United Airlines
7.4
Good
9,215 reviews

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

Crew

8.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
American Airlines
7.2
Good
11,205 reviews
United Airlines
7.4
Good
9,215 reviews

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

Crew

8.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.

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 American Airlines and United Airlines fly from South Padre Island to Chicago in about 5h 42m. The time it takes to get you to your destination can typically vary by up to 1h 38m. 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 $136). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$159Average$375FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$252Average$319FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$268Average$407FlexibilityNo cancel feeOn-time69%

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