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$300+ 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 7/12. Fares are subject to change and may not be available on all flights or dates of travel.
MFE — CHI
Jun 29 — Jul 61
Mon 6/29
Mon 7/6
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 May 30, 2026.

This American Airlines deal was found by Cheapflights users on 5/30. 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 7/226:42 pm
BRO
-
ORD
1 stop6h 08m
American Airlines
Sat 7/254:51 pm
ORD
-
BRO
1 stop7h 22m
American Airlines
Deal found 5/30$329
This United Airlines deal was found by Cheapflights users on 5/26. 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.
Mon 6/154:44 pm
BRO
-
ORD
1 stop8h 01m
United Airlines
Sat 6/206:30 am
ORD
-
BRO
1 stop4h 56m
United Airlines
Deal found 5/26$364
This American Airlines deal was found by Cheapflights users on 5/25. 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 6/2910:50 am
ORD
-
BRO
1 stop7h 22m
American Airlines
Deal found 5/25$395
This Kiwi.com deal was found by Cheapflights users on 5/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/48:35 am
BRO
-
ORD
1 stop14h 39m
Multiple Airlines
Thu 9/109:26 am
ORD
-
BRO
1 stop22h 39m
Multiple Airlines
Deal found 5/28$405
This United Airlines deal was found by Cheapflights users on 5/28. 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.
Tue 9/112:05 pm
BRO
-
ORD
1 stop6h 25m
United Airlines
Sat 9/512:47 pm
ORD
-
BRO
1 stop5h 26m
United Airlines
Deal found 5/28$419
This Kiwi.com deal was found by Cheapflights users on 5/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/48:35 am
BRO
-
ORD
1 stop14h 39m
Multiple Airlines
Sun 9/61:50 pm
ORD
-
BRO
2 stops18h 05m
Multiple Airlines
Deal found 5/28$426
This Kiwi.com deal was found by Cheapflights users on 5/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/78:35 am
BRO
-
ORD
2 stops11h 20m
Multiple Airlines
Thu 9/104:49 pm
ORD
-
BRO
1 stop15h 16m
Multiple Airlines
Deal found 5/28$427
This United Airlines deal was found by Cheapflights users on 5/28. 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.
Sat 9/54:38 pm
BRO
-
ORD
1 stop6h 48m
United Airlines
Fri 10/95:30 am
ORD
-
BRO
1 stop5h 53m
United Airlines
Deal found 5/28$429
This United Airlines deal was found by Cheapflights users on 5/25. 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 6/54:44 pm
BRO
-
ORD
1 stop5h 07m
United Airlines
Tue 6/96:30 am
ORD
-
BRO
1 stop4h 56m
United Airlines
Deal found 5/25$434

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 May 30, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$329
(American Airlines)

One-way from

$300
(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 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. 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 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 May 30, 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

Tue 10/20

4:38 pm-12:23 am

1 stop7h 45m

Chicago O'Hare Intl

Sat 10/24

4:11 pm-9:28 pm

1 stop5h 17m

$419

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Sat 6/27

4:44 pm-11:14 pm

1 stop6h 30m

Chicago O'Hare Intl

Tue 6/30

12:40 pm-6:37 pm

1 stop5h 57m

$419

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Tue 9/1

9:20 am-4:41 pm

1 stop7h 21m

Chicago O'Hare Intl

Wed 9/9

8:50 am-3:51 pm

1 stop7h 01m

$419

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Thu 6/25

4:44 pm-12:45 am

1 stop8h 01m

Chicago O'Hare Intl

Wed 7/1

6:29 am-11:26 am

1 stop4h 57m

$446

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Tue 9/1

12:05 pm-8:05 pm

1 stop8h 00m

Chicago O'Hare Intl

Tue 9/8

8:50 am-3:51 pm

1 stop7h 01m

$454
Quickest round-trip

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Fri 7/31

6:42 pm-12:50 am

1 stop6h 08m

Chicago O'Hare Intl

Mon 8/3

6:19 pm-12:13 am

1 stop5h 54m

$484

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Thu 9/3

4:38 pm-12:59 am

1 stop8h 21m

Chicago O'Hare Intl

Sat 9/5

12:47 pm-6:13 pm

1 stop5h 26m

$500

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Tue 6/23

12:10 pm-6:28 am

2 stops18h 18m

Chicago O'Hare Intl

Tue 6/30

10:30 am-6:37 pm

1 stop8h 07m

$513

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Fri 6/26

4:44 pm-12:46 am

1 stop8h 02m

Chicago O'Hare Intl

Sat 7/4

6:29 am-2:02 pm

1 stop7h 33m

$540
Cheapest one-way
Quickest one-way

BrownsvilleChicago

BRO - ORD

BROORD

Brownsville South Padre Is. Intl

Sun 7/12

6:42 pm-12:50 am

1 stop6h 08m

$300

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/28

Showing 1-10 of 13 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?

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 30, 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
9,766 reviews

Boarding

7.7

Entertainment

7.1

Crew

8.1

Overall

7.4

Food

6.6

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
9,766 reviews
United Airlines
7.4
Good
9,766 reviews

Boarding

7.7

Entertainment

7.1

Crew

8.1

Overall

7.4

Food

6.6

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
11,640 reviews
United Airlines
7.4
Good
9,766 reviews

Boarding

7.7

Entertainment

7.1

Crew

8.1

Overall

7.4

Food

6.6

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 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 7h 45m. 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
Hammond
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 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 May 30, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$159Average$427FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$250Average$423FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$252Average$328FlexibilityNo cancel feeOn-time63%

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