$103 Flight Deals from San Antonio to Chicago

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... and +100s more

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Price Drop Deals Near You

Chicago

21% Price Drop

Jul 21

SAT

3 days

Jul 24

ORD

$289

now only

^$228

Round Trip

34% Price Drop

Aug 13

SAT

3 days

Aug 16

MDW

$372

now only

^$245

Round Trip

Chicago

18% Price Drop

Aug 29

SAT

5 days

Sep 3

ORD

$289

now only

^$236

Round Trip

Chicago

14% Price Drop

Aug 7

SAT

3 days

Aug 10

ORD

$289

now only

^$247

Round Trip

31% Price Drop

Aug 6

SAT

4 days

Aug 10

MDW

$372

now only

^$257

Round Trip

31% Price Drop

Aug 5

SAT

5 days

Aug 10

MDW

$372

now only

^$259

Round Trip

13% Price Drop

Jul 25

SAT

5 days

Jul 30

MDW

$372

now only

^$324

Round Trip

Stops

Nonstop
from $469
Up to 1 stop
$479

Airlines

Alaska Airlines
$748
American Airlines
$472
Hawaiian Airlines
$801
United Airlines
$469

Cabin Class

Economy
$469

Departure Airports

San Antonio International Airport
$469

Arrival Airports

Chicago O Hare Airport
$469

Layover Airports

Dallas Fort Worth International Airport
$482
Denver International Airport
$516
George Bush Intercontinental Houston Airport
$479
Seattle Tacoma International Airport
$748

Best Price. GUARANTEED.

Exclusively for Priceline Members
Tired of searching? Book now!
We'll refund the difference if you find a lower price.

BUNDLE & SAVE

Book a flight & hotel together for extra savings.

On average save $240 per traveler

EXPRESS DEAL

BUDGET FRIENDLY

You’re guaranteed to get one of these airlines:

Delta

Alaska

United

American

SAT ORD

Jul 04 - Jul 07 ‧ Economy

^$536

Round Trip

BUDGET FRIENDLY

You’re guaranteed to get one of these airlines:

Delta

Alaska

United

American

SAT ORD

Jun 28 ‧ Economy

^$196

One Way

United Airlines

11/21/25

2:01pm

SAT

2h 46m

Direct

11/21/25

4:47pm

ORD

United Airlines

11/25/25

9:17am

ORD

3h 15m

Direct

11/25/25

12:32pm

SAT

^$469

American Airlines

11/21/25

3:04pm

SAT

2h 51m

Direct

11/21/25

5:55pm

ORD

American Airlines

11/25/25

8:25pm

ORD

3h 5m

Direct

11/25/25

11:30pm

SAT

^$472

United Airlines

11/21/25

2:01pm

SAT

2h 46m

Direct

11/21/25

4:47pm

ORD

United Airlines

11/25/25

5:50pm

ORD

5h 6m

IAH

11/25/25

10:56pm

SAT

^$479

American Airlines

11/21/25

4:40pm

SAT

2h 51m

Direct

11/21/25

7:31pm

ORD

American Airlines

11/25/25

9:00am

ORD

5h 28m

DFW

11/25/25

2:28pm

SAT

^$482

United Airlines

11/21/25

5:30am

SAT

5h 26m

IAH

11/21/25

10:56am

ORD

United Airlines

11/25/25

5:50pm

ORD

5h 6m

IAH

11/25/25

10:56pm

SAT

^$488

United Airlines

11/23/25

2:01pm

SAT

2h 46m

Direct

11/23/25

4:47pm

ORD

United Airlines

11/28/25

9:17am

ORD

3h 15m

Direct

11/28/25

12:32pm

SAT

^$497

American Airlines

11/23/25

4:40pm

SAT

2h 51m

Direct

11/23/25

7:31pm

ORD

American Airlines

11/28/25

8:25pm

ORD

3h 5m

Direct

11/28/25

11:30pm

SAT

^$498

United Airlines

11/23/25

2:01pm

SAT

2h 46m

Direct

11/23/25

4:47pm

ORD

United Airlines

11/28/25

7:10am

ORD

5h 54m

IAH

11/28/25

1:04pm

SAT

^$507

American Airlines

11/23/25

3:04pm

SAT

2h 51m

Direct

11/23/25

5:55pm

ORD

American Airlines

11/28/25

7:00am

ORD

6h 36m

DFW

11/28/25

1:36pm

SAT

^$508

United Airlines

11/23/25

4:30pm

SAT

7h 29m

DEN

11/23/25

11:59pm

ORD

United Airlines

11/28/25

5:50pm

ORD

5h 6m

IAH

11/28/25

10:56pm

SAT

^$516

American Airlines

11/21/25

6:40pm

SAT

5h 10m

DFW

11/21/25

11:50pm

ORD

American Airlines

11/25/25

11:45am

ORD

5h 11m

DFW

11/25/25

4:56pm

SAT

^$517

American Airlines

11/23/25

6:40pm

SAT

5h 10m

DFW

11/23/25

11:50pm

ORD

American Airlines

11/28/25

8:05am

ORD

5h 31m

DFW

11/28/25

1:36pm

SAT

^$518

Alaska Airlines

11/22/25

7:00am

SAT

10h 50m

SEA

11/22/25

5:50pm

ORD

Alaska Airlines

11/28/25

7:45am

ORD

10h 13m

SEA

11/28/25

5:58pm

SAT

^$748

Hawaiian Airlines

11/21/25

7:00am

SAT

10h 50m

SEA

11/21/25

5:50pm

ORD

Hawaiian Airlines

11/25/25

7:45am

ORD

10h 13m

SEA

11/25/25

5:58pm

SAT

^$801

Top Deals on flights from San Antonio to Chicago

San Antonio, US (SAT) - Chicago, US (CHI)

Sep 23

6:00am

SAT

8h 16m

LAS

Sep 23

2:16pm

ORD

as low as

^$103

San Antonio, US (SAT) - Chicago, US (CHI)

Oct 14

5:20am

SAT

7h 19m

DTW

Oct 14

12:39pm

ORD

as low as

^$108

San Antonio, US (SAT) - Chicago, US (CHI)

Sep 15

4:25pm

SAT

5h 19m

ATL

Sep 15

9:44pm

MDW

as low as

^$108

San Antonio, US (SAT) - Chicago, US (CHI)

Oct 1

6:45am

SAT

5h 23m

ATL

Oct 1

12:08pm

ORD

as low as

^$108

San Antonio, US (SAT) - Chicago, US (CHI)

Sep 5

5:20am

SAT

8h 55m

MCO

Sep 5

2:15pm

ORD

as low as

^$109

San Antonio, US (SAT) - Chicago, US (CHI)

Aug 16

4:29pm

SAT

7h 30m

FLL

Aug 16

11:59pm

ORD

as low as

^$127

San Antonio, US (SAT) - Chicago, US (CHI)

Aug 26

7:30am

SAT

10h

SLC

Aug 26

5:30pm

ORD

as low as

^$127

San Antonio, US (SAT) - Chicago, US (CHI)

United Airlines

Sep 22

5:15pm

SAT

2h 52m

Direct

Sep 22

8:07pm

ORD

as low as

^$138

San Antonio, US (SAT) - Chicago, US (CHI)

Aug 27

8:28pm

SAT

9h 32m

LAX

Aug 28

6:00am

ORD

as low as

^$139

San Antonio, US (SAT) - Chicago, US (CHI)

Oct 13

5:35pm

SAT

6h 35m

ATL

Oct 14

12:10am

ORD

as low as

^$148

San Antonio, US (SAT) - Chicago, US (CHI)

Oct 4

2:55pm

SAT

8h 58m

DEN

Oct 4

11:53pm

ORD

as low as

^$148

San Antonio, US (SAT) - Chicago, US (CHI)

United Airlines

Sep 22

4:22pm

SAT

6h 19m

IAH

Sep 22

10:41pm

ORD

as low as

^$148

Frequently Asked Questions

What are the most convenient layover airports for the flight?

The most convenient layover airports for your flight are George Bush Intercontinental (United Airlines), Dallas Fort Worth International (American Airlines), Seattle Tacoma International (Alaska Airlines), and Seattle Tacoma International (Hawaiian Airlines).

What is the cheapest and fastest flight from San Antonio to Chicago?

The cheapest flight is with United Airlines at $469, taking 2 hours 46 minutes. No faster option is available.

What are all possible destination arrival airports?

The possible destination arrival airport for your flight is Chicago O'Hare Airport.

What is the time difference between destination and arrival?

The flight from San Antonio to Chicago will take approximately 2 hours and 46 minutes, but you should also consider the time zone difference, as Chicago is typically one hour ahead of San Antonio.

Is there a direct flight from San Antonio to Chicago?

Yes, there are direct flights from San Antonio International Airport to Chicago O Hare Airport. United Airlines offers a non-stop flight priced at $469, taking 2 hours 46 minutes. American Airlines also provides a non-stop flight for $472, with a flight time of 2 hours 51 minutes.

Are there convenient layover flights from San Antonio to Chicago?

Yes, there are convenient layover flights from San Antonio to Chicago. Airlines include United Airlines at $488, American Airlines at $517, Alaska Airlines at $748, and Hawaiian Airlines at $801. Layovers vary by airline and total travel times range from 5 hours 10 minutes to 10 hours 50 minutes.

Flights to Chicago

Top Destinations

Origins

Return flights

Cabin Class

Flight Deals from San Antonio to Chicago from $103

Price Drop Deals Near You

Stops

Airlines

Cabin Class

Departure Airports

Arrival Airports

Layover Airports

Best Price. GUARANTEED.

Top Deals on flights from San Antonio to Chicago

Frequently Asked Questions

Flights to Chicago