S$165 Cheap Flights from San Diego to Chicago

View S$165 flight on Mon, 25 Aug, 2025Opens in a new window

Popular airlines from San Diego Intl. Airport (SAN) to Chicago O'Hare Intl. Airport (ORD)

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Cheap Flights from San Diego to Chicago (SAN-ORD)

Prices were available within the past 7 days and start at S$165 for one-way flights and S$328 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, 5 Aug - Tue, 12 Aug
SAN
San Diego
ORD
Chicago
S$328 Return, found 4 days ago
S$328
Return
found 4 days ago
Select Delta flight, departing Tue, 5 Aug from San Diego to Chicago, returning Tue, 12 Aug, priced at S$328 found 4 days ago
United
Tue, 5 Aug - Tue, 12 Aug
SAN
San Diego
ORD
Chicago
S$332 Return, found 4 days ago
S$332
Return
found 4 days ago
Select United flight, departing Tue, 5 Aug from San Diego to Chicago, returning Tue, 12 Aug, priced at S$332 found 4 days ago
American Airlines
Tue, 5 Aug - Tue, 12 Aug
SAN
San Diego
ORD
Chicago
S$334 Return, found 4 days ago
S$334
Return
found 4 days ago
Select American Airlines flight, departing Tue, 5 Aug from San Diego to Chicago, returning Tue, 12 Aug, priced at S$334 found 4 days ago
United
Tue, 5 Aug - Tue, 12 Aug
SAN
San Diego
ORD
Chicago
S$334 Return, found 4 days ago
S$334
Return
found 4 days ago
Select United flight, departing Tue, 5 Aug from San Diego to Chicago, returning Tue, 12 Aug, priced at S$334 found 4 days ago
American Airlines
Wed, 13 Aug - Wed, 20 Aug
CLD
Carlsbad
ORD
Chicago
S$347 Return, found 5 days ago
S$347
Return
found 5 days ago
Select American Airlines flight, departing Wed, 13 Aug from Carlsbad to Chicago, returning Wed, 20 Aug, priced at S$347 found 5 days ago
United
Tue, 5 Aug - Tue, 12 Aug
SAN
San Diego
ORD
Chicago
S$361 Return, found 4 days ago
S$361
Return
found 4 days ago
Select United flight, departing Tue, 5 Aug from San Diego to Chicago, returning Tue, 12 Aug, priced at S$361 found 4 days ago
United
Tue, 5 Aug - Tue, 12 Aug
SAN
San Diego
ORD
Chicago
S$363 Return, found 4 days ago
S$363
Return
found 4 days ago
Select United flight, departing Tue, 5 Aug from San Diego to Chicago, returning Tue, 12 Aug, priced at S$363 found 4 days ago
Delta
Wed, 13 Aug - Wed, 20 Aug
SAN
San Diego
ORD
Chicago
S$368 Return, found 5 days ago
S$368
Return
found 5 days ago
Select Delta flight, departing Wed, 13 Aug from San Diego to Chicago, returning Wed, 20 Aug, priced at S$368 found 5 days ago
United
Wed, 13 Aug - Wed, 20 Aug
SAN
San Diego
ORD
Chicago
S$373 Return, found 5 days ago
S$373
Return
found 5 days ago
Select United flight, departing Wed, 13 Aug from San Diego to Chicago, returning Wed, 20 Aug, priced at S$373 found 5 days ago
United
Wed, 13 Aug - Wed, 20 Aug
SAN
San Diego
ORD
Chicago
S$376 Return, found 5 days ago
S$376
Return
found 5 days ago
Select United flight, departing Wed, 13 Aug from San Diego to Chicago, returning Wed, 20 Aug, priced at S$376 found 5 days ago

Find the cheapest month to fly from San Diego (SAN) to Chicago (ORD)

September is typically the cheapest month to fly

From S$116 - S$211 per traveller.

Graph displaying average flight prices per month

San Diego to Chicago route information
Origin airport
San Diego Intl.
Destination airport
O'Hare Intl.
Return price
S$328
Distance
2752 km
Average flight time
6 hours 15 mins

Frequently asked questions

How much is a flight from San Diego Intl. Airport (SAN) to O'Hare Intl. Airport (ORD)?
If you're planning on travelling between SAN and ORD, round-trip journeys start from S$328. This figure is based on fares quoted within the last 7 days on Expedia for flights departing within the next year, so don't let a good deal slip through your fingers. Book today and save yourself money and time. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from SAN to ORD?
The majority of flights can be cancelled online, but whether you are charged a fee differs between airlines. If you do have to cancel your trip, follow the easy instructions in the Customer Service Portal.
How do I find cheap flights from San Diego Airport to O'Hare Intl. Airport (ORD) that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for San Diego Intl. Airport (SAN) to O'Hare Intl. Airport (ORD) flights, you'll see a "no change fees" filter for you to select.
How far is the flight from San Diego Intl. Airport (SAN) to ORD?
The flying distance between SAN and O'Hare Airport is 2,800 kilometres. Squeeze in a nap or make a start on the latest bestseller and the journey will zip by.
Which airlines fly direct from San Diego Airport to O'Hare Intl. Airport (ORD)?
A leading airline that flies from San Diego Intl. Airport (SAN) to O'Hare Intl. Airport (ORD) is United Airlines (UA). It offers 121 flights monthly. If you'd like more options, check out the ticket prices from American Airlines (AA). This airlines operates 91 flights a month between these airports.
Are San Diego Intl. Airport (SAN) to O'Hare Airport flight tickets cheaper when they're purchased at the last minute?
It is possible to pick up amazing last-minute deals from San Diego Intl. Airport (SAN) to O'Hare Airport, but it can also be hit-or-miss. As many airlines publish prices up to a year in advance, it's worthwhile keeping an eye on fares early and being ready to book when you spot a bargain. Expedia compares air carrier prices and updates flight deals often, so you can rest assured you're always getting the latest offers.

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