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Cheap flights from San Diego to Chicago from $41

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from San Diego to Chicago departing on 8/20. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap round-trip flights

Spirit Airlines Logo
7:01 pm - 4:50 amSAN-ORD
7h 49m1 stop
Spirit Airlines Logo
6:00 am - 5:56 pmORD-SAN
13h 56m1 stop
$108Spirit Airlines
Find Deal
Thu, Aug 14 - Tue, Aug 19
Spirit Airlines Logo
7:01 pm - 11:43 amSAN-ORD
14h 42m1 stop
Spirit Airlines Logo
6:21 pm - 11:37 pmORD-SAN
7h 16m1 stop
$111Spirit Airlines
Find Deal
Wed, Aug 20 - Tue, Aug 26
Logo
7:01 pm - 4:50 amSAN-ORD
7h 49m1 stop
Logo
7:55 am - 10:30 amORD-SAN
4h 35mnonstop
$112
Find Deal
Wed, Sep 3 - Sun, Sep 7
Frontier Logo
3:40 pm - 10:03 pmSAN-ORD
4h 23mnonstop
Frontier Logo
7:00 am - 9:20 amORD-SAN
4h 20mnonstop
$122Frontier
Find Deal
Fri, Aug 29 - Mon, Sep 1
Frontier Logo
3:40 pm - 10:03 pmSAN-ORD
4h 23mnonstop
Frontier Logo
7:55 am - 10:30 amORD-SAN
4h 35mnonstop
$130Frontier
Find Deal
Thu, Aug 28 - Thu, Sep 4
United Airlines Logo
6:40 am - 12:59 pmSAN-ORD
4h 19mnonstop
United Airlines Logo
4:00 pm - 6:20 pmORD-SAN
4h 20mnonstop
$134United Airlines
Find Deal
Sat, Sep 6 - Sat, Sep 6
American Airlines Logo
3:07 pm - 9:24 pmSAN-ORD
4h 17mnonstop
American Airlines Logo
5:05 pm - 7:27 pmORD-SAN
4h 22mnonstop
$139American Airlines
Find Deal
Sat, Aug 30 - Sat, Sep 6
American Airlines Logo
1:08 pm - 7:25 pmSAN-ORD
4h 17mnonstop
American Airlines Logo
5:05 pm - 7:27 pmORD-SAN
4h 22mnonstop
$140American Airlines
Find Deal
Sat, Aug 30 - Sat, Sep 6
United Airlines Logo
2:11 pm - 8:25 pmSAN-ORD
4h 14mnonstop
United Airlines Logo
7:35 pm - 10:02 pmORD-SAN
4h 27mnonstop
$148United Airlines
Find Deal
Tue, Aug 26 - Wed, Sep 3
Alaska Airlines Logo
5:19 pm - 11:59 pmSAN-ORD
4h 40mnonstop
Alaska Airlines Logo
2:54 pm - 5:19 pmORD-SAN
4h 25mnonstop
$168Alaska Airlines
Find Deal
Sat, Oct 18 - Sun, Oct 26

American Airlines flights from San Diego to Chicago O'Hare Intl Airport

Our best American Airlines deals on San Diego to Chicago O'Hare Intl Airport flight tickets
American Airlines
Aug 30
SAN3:07 pmSan Diego
4h 17m
ORD9:24 pmChicago O'Hare Intl
Sep 6
ORD5:05 pmChicago O'Hare Intl
4h 22m
SAN7:27 pmSan Diego
$139
Find similar
American Airlines
Aug 30
SAN1:08 pmSan Diego
4h 17m
ORD7:25 pmChicago O'Hare Intl
Sep 6
ORD5:05 pmChicago O'Hare Intl
4h 22m
SAN7:27 pmSan Diego
$140
Find similar
American Airlines
Aug 26
SAN1:08 pmSan Diego
4h 17m
ORD7:25 pmChicago O'Hare Intl
Aug 30
ORD4:55 pmChicago O'Hare Intl
4h 21m
SAN7:16 pmSan Diego
$149
Find similar

Spirit Airlines flights from San Diego to Chicago O'Hare Intl Airport

Our best Spirit Airlines deals on San Diego to Chicago O'Hare Intl Airport flight tickets
Spirit Airlines
Aug 14
SAN7:01 pmSan Diego
7h 49m
1 stop
ORD4:50 amChicago O'Hare Intl
Aug 19
ORD6:00 amChicago O'Hare Intl
13h 56m
1 stop
SAN5:56 pmSan Diego
$108
Find similar
Spirit Airlines
Aug 20
SAN7:01 pmSan Diego
14h 42m
1 stop
ORD11:43 amChicago O'Hare Intl
Aug 26
ORD6:21 pmChicago O'Hare Intl
7h 16m
1 stop
SAN11:37 pmSan Diego
$111
Find similar
Spirit Airlines
Aug 19
SAN6:15 amSan Diego
9h 00m
1 stop
ORD5:15 pmChicago O'Hare Intl
Aug 23
ORD5:35 pmChicago O'Hare Intl
8h 02m
1 stop
SAN11:37 pmSan Diego
$117
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from San Diego to Chicago O'Hare Intl Airport 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, momondo users made 832,500 searches. Data last updated July 31, 2025.
Use the filters below to find and compare flights from San Diego to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

San DiegoChicago

SAN - ORD

SANORD

San Diego

Thu 8/14

7:01 pm-4:50 am

1 stop7h 49m

Chicago O'Hare Intl

Tue 8/19

6:00 am-5:56 pm

1 stop13h 56m

$108

San DiegoChicago

SAN - ORD

SANORD

San Diego

Wed 8/20

7:01 pm-11:43 am

1 stop14h 42m

Chicago O'Hare Intl

Tue 8/26

6:21 pm-11:37 pm

1 stop7h 16m

$111

San DiegoChicago

SAN - ORD

SANORD

San Diego

Wed 9/3

7:01 pm-4:50 am

1 stop7h 49m

Chicago O'Hare Intl

Sun 9/7

7:55 am-10:30 am

Nonstop4h 35m

$112

San DiegoChicago

SAN - ORD

SANORD

San Diego

Fri 8/29

3:40 pm-10:03 pm

Nonstop4h 23m

Chicago O'Hare Intl

Mon 9/1

7:00 am-9:20 am

Nonstop4h 20m

$122

San DiegoChicago

SAN - ORD

SANORD

San Diego

Thu 8/28

3:40 pm-10:03 pm

Nonstop4h 23m

Chicago O'Hare Intl

Thu 9/4

7:55 am-10:30 am

Nonstop4h 35m

$130

San DiegoChicago

SAN - ORD

SANORD

San Diego

Sat 9/6

6:40 am-12:59 pm

Nonstop4h 19m

Chicago O'Hare Intl

Sat 9/6

4:00 pm-6:20 pm

Nonstop4h 20m

$134

San DiegoChicago

SAN - ORD

SANORD

San Diego

Sat 8/30

3:07 pm-9:24 pm

Nonstop4h 17m

Chicago O'Hare Intl

Sat 9/6

5:05 pm-7:27 pm

Nonstop4h 22m

$139

San DiegoChicago

SAN - ORD

SANORD

San Diego

Sat 8/30

1:08 pm-7:25 pm

Nonstop4h 17m

Chicago O'Hare Intl

Sat 9/6

5:05 pm-7:27 pm

Nonstop4h 22m

$140

San DiegoChicago

SAN - ORD

SANORD

San Diego

Tue 8/26

2:11 pm-8:25 pm

Nonstop4h 14m

Chicago O'Hare Intl

Wed 9/3

7:35 pm-10:02 pm

Nonstop4h 27m

$148

San DiegoChicago

SAN - ORD

SANORD

San Diego

Sat 10/18

5:19 pm-11:59 pm

Nonstop4h 40m

Chicago O'Hare Intl

Sun 10/26

2:54 pm-5:19 pm

Nonstop4h 25m

$168

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from San Diego to Chicago O'Hare Intl Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between San Diego and Chicago O'Hare Intl Airport?

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The month of July is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from San Diego averaging around $315.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Wednesday when prices can be found for as low as $441. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from San Diego because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $597.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from San Diego in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $258 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $527. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest San Diego to Chicago O'Hare Intl flight route?

Fly from San Diego to Chicago O'Hare Intl for the best San Diego - Chicago O'Hare Intl flight prices

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from San Diego when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $389 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from San Diego for as low as $302 on momondo.

What cabin class options are available on San Diego to Chicago O'Hare Intl flights?

There are 4 cabin classes available to choose from on San Diego to Chicago O'Hare Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on San Diego to Chicago O'Hare Intl Airport flights?

You could potentially save up to 12% on your flight if you consider stops on a San Diego to Chicago O'Hare Intl Airport flight.

How have San Diego to Chicago O'Hare Intl Airport flight prices changed over time?

As of July 2025, prices for San Diego to Chicago O'Hare Intl Airport flights are approximately 62% cheaper when compared to flights at the same time last year.

When to book flights from San Diego to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from San Diego to Chicago O'Hare Intl Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap San Diego to Chicago O'Hare Intl Airport (SAN to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from San Diego to Chicago O'Hare Intl Airport

Best Price Found

$41

Fastest flight time

4h 07m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from San Diego in the past 72 hours is $41. The best round-trip flight deal from San Diego to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $108.
The fastest flight from San Diego to Chicago O'Hare Intl Airport takes 4h 07m
Direct flights go from San Diego to Chicago O'Hare Intl Airport every day.
Search flight deals

  • How far is San Diego to Chicago O'Hare Intl by plane?

    A flight from San Diego to Chicago O'Hare Intl will travel around 1717.8 mi. Typically, this will take 4h 07m by plane in normal conditions.

  • When did momondo last update prices for flights from San Diego Airport to Chicago O'Hare Intl Airport?

    Prices for flights from San Diego Airport to Chicago O'Hare Intl Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from San Diego Airport to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from San Diego Airport to Chicago O'Hare Intl Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from San Diego Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The required travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago O'Hare Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from San Diego to Chicago O'Hare Intl Airport?

  • What is the most popular airline from San Diego to Chicago O'Hare Intl Airport?

Best airlines flying from San Diego to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from San Diego to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $94Free CancellationRating
6.3
8,049 reviews
Search Spirit Airlines flights
FrontierPriceFrom $116Free CancellationRating
5.9
3,239 reviews
Search Frontier flights
Alaska AirlinesPriceFrom $184Free CancellationRating
8.0
10,000 reviews
Search Alaska Airlines flights
American AirlinesPriceFrom $185Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $241Free CancellationRating
7.4
8,900 reviews
Search United Airlines flights
DeltaPriceFrom $280Free CancellationRating
8.0
7,981 reviews
Search Delta flights

  • Alaska Airlines Flights From San Diego to Chicago O'Hare Intl Airport

    Across 30 Alaska Airlines flights from San Diego to Chicago O'Hare Intl Airport this week, the average price was $608, with the best Alaska Airlines deals starting from $184 round-trip. 10,000 users have rated Alaska Airlines on momondo, with an average score of 8.0/10.

  • United Airlines Flights From San Diego to Chicago O'Hare Intl Airport

    United Airlines is also a popular choice for this route. United Airlines flight deals for San Diego to Chicago O'Hare Intl Airport start from as low as $241 round-trip, depending on your selected dates, with average United Airlines deals seen on momondo around $460. United Airlines operates 11 flights to Chicago O'Hare Intl Airport from San Diego in an average week. Users have rated it 7.4/10 across 8,900 reviews.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Rockford
Schaumburg
South Haven
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Racine
Hammond
Tinley Park
Elgin
Orland Park
Aurora
Janesville
Benton Harbor

Why use momondo?

Why should I use momondo to find a flight deal from San Diego to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from San Diego to Chicago. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from San Diego to Chicago with flexible booking policies on momondo?

All flight searches from San Diego to Chicago on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from San Diego to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from San Diego. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from San Diego to Chicago right now. Can momondo alert me if prices change?

If you are not ready to book a flight from San Diego to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

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