How often are flights from San Diego to Chicago delayed?

Historically, on average around 9% of flights between San Diego and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 171 minutes.

What is the cheapest airline that flies from San Diego to Chicago?

United Airlines, Southwest, and Alaska Airlines are the most popular carriers operating from San Diego to Chicago

How many flights depart from San Diego to Chicago on average per day?

30 flights are operational daily from San Diego to Chicago as of November 2025. The most popular departure time for this route is 6:00AM, with 60% of flights per day taking off at noon.

What day of the week experiences the fewest flight delays on this route?

Monday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

How many flights depart from San Diego to Chicago on average per week?

The number of flights available between San Diego and Chicago is 213 per week as of November 2025. The most frequent departure day is Mon, with 21% of weekly flights leaving on this day.

What is the most punctual flight time for San Diego to Chicago flights?

Generally, flights departing at night tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

Which airline has the best punctuality record on San Diego to Chicago flights?

According to our data, Air Canada have had the least number of delays on this route over the last 12 months; with no flights being classified as delayed.

What airlines fly to Chicago?

American Airlines, United Airlines and Frontier are the top three most popular airlines that fly to Chicago from San Diego according to our data. American Airlines is the first choice among our users, with 51% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 8 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

When did momondo last update prices for flights from San Diego Airport to Chicago?

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

How many operators does momondo search for flights from San Diego Airport to Chicago?

As of November 2025, there are 8 operators available to choose from for flights from San Diego Airport to Chicago.

How old do you have to be to fly from San Diego Airport to Chicago?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from San Diego Airport to Chicago.

What documentation or ID do you need to fly to Chicago?

The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$84 Cheap Flights from San Diego to Chicago in 2025/26

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Cheap round-trip flights

Enter your travel dates to find the best prices.

5:42 pm - 11:59 pmSAN-ORD

4h 17mnonstop

8:20 am - 11:09 amORD-SAN

4h 49mnonstop

$153Alaska Airlines

Find Deal

Sat, Feb 14 - Tue, Feb 17

5:10 pm - 11:37 pmSAN-ORD

4h 27mnonstop

3:44 pm - 6:26 pmORD-SAN

4h 42mnonstop

$155Alaska Airlines

Find Deal

Tue, Jan 20 - Wed, Jan 28

7:25 am - 1:20 pmSAN-MDW

3h 55mnonstop

8:25 am - 11:05 amMDW-SAN

4h 40mnonstop

$155Southwest

Find Deal

Sat, Jan 10 - Sat, Jan 17

6:20 am - 12:29 pmSAN-ORD

4h 09mnonstop

10:35 am - 1:11 pmORD-SAN

4h 36mnonstop

$156American Airlines

Find Deal

Sat, Jan 10 - Sat, Jan 17

6:25 am - 12:25 pmSAN-MDW

4h 00mnonstop

7:40 pm - 10:10 pmMDW-SAN

4h 30mnonstop

$157Southwest

Find Deal

Tue, Jan 13 - Sat, Jan 31

5:10 pm - 11:37 pmSAN-ORD

4h 27mnonstop

3:44 pm - 6:26 pmORD-SAN

4h 42mnonstop

$157Alaska Airlines

Find Deal

Wed, Jan 21 - Wed, Jan 28

8:00 am - 2:29 pmSAN-ORD

4h 29mnonstop

9:00 am - 5:03 pmORD-SAN

10h 03m1 stop

$159Multiple Airlines

Find Deal

Mon, Jan 12 - Thu, Jan 22

7:50 pm - 5:12 amSAN-ORD

7h 22m1 stop

8:47 am - 11:38 amORD-SAN

4h 51mnonstop

$161United Airlines

Find Deal

Wed, Feb 18 - Wed, Feb 25

6:36 am - 12:42 amSAN-ORD

16h 06m2 stops

10:07 pm - 7:37 pmORD-SAN

23h 30m1 stop

$162Frontier

Find Deal

Fri, Jan 9 - Sun, Jan 11

6:25 am - 7:54 pmSAN-MDW

11h 29m1 stop

8:19 pm - 10:13 amMDW-SAN

15h 54m1 stop

$162Frontier

Find Deal

Fri, Jan 16 - Sun, Jan 18

American Airlines flights from San Diego to Chicago

Our best American Airlines deals on San Diego to Chicago flight tickets

American Airlines

Jan 10

SAN6:20 amSan Diego

4h 09m

ORD12:29 pmChicago O'Hare Intl

Jan 17

ORD10:35 amChicago O'Hare Intl

4h 36m

SAN1:11 pmSan Diego

$156

Find similar

American Airlines

Jan 9

SAN3:02 pmSan Diego

4h 13m

ORD9:15 pmChicago O'Hare Intl

Jan 16

ORD7:50 pmChicago O'Hare Intl

4h 36m

SAN10:26 pmSan Diego

$178

Find similar

American Airlines

Dec 9

SAN6:15 amSan Diego

4h 16m

ORD12:31 pmChicago O'Hare Intl

Dec 10

ORD6:10 pmChicago O'Hare Intl

4h 35m

SAN8:45 pmSan Diego

$231

Find similar

Frontier flights from San Diego to Chicago

Our best Frontier deals on San Diego to Chicago flight tickets

Frontier

Jan 9

SAN6:36 amSan Diego

16h 06m

2 stops

ORD12:42 amChicago O'Hare Intl

Jan 11

ORD10:07 pmChicago O'Hare Intl

23h 30m

1 stop

SAN7:37 pmSan Diego

$162

Find similar

Frontier

Feb 13

SAN8:00 amSan Diego

26h 47m

1 stop

ORD12:47 pmChicago O'Hare Intl

Feb 19

ORD7:51 pmChicago O'Hare Intl

17h 35m

1 stop

SAN11:26 amSan Diego

$163

Find similar

Frontier

Jan 10

SAN2:46 pmSan Diego

18h 59m

1 stop

MDW11:45 amChicago Midway

Jan 17

MDW6:10 amChicago Midway

18h 57m

2 stops

SAN11:07 pmSan Diego

$169

Find similar

Fly from

Fly to

Route

Depart

Return

Price

San DiegoChicago

SAN - ORD

SANORD

San Diego

Sat 2/14

5:42 pm-11:59 pm

Nonstop4h 17m

Chicago O'Hare Intl

Tue 2/17

8:20 am-11:09 am

Nonstop4h 49m

$153

San DiegoChicago

SAN - ORD

SANORD

San Diego

Tue 1/20

5:10 pm-11:37 pm

Nonstop4h 27m

Chicago O'Hare Intl

Wed 1/28

3:44 pm-6:26 pm

Nonstop4h 42m

$155

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Sat 1/10

7:25 am-1:20 pm

Nonstop3h 55m

Chicago Midway

Sat 1/17

8:25 am-11:05 am

Nonstop4h 40m

$155

San DiegoChicago

SAN - ORD

SANORD

San Diego

Sat 1/10

6:20 am-12:29 pm

Nonstop4h 09m

Chicago O'Hare Intl

Sat 1/17

10:35 am-1:11 pm

Nonstop4h 36m

$156

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Tue 1/13

6:25 am-12:25 pm

Nonstop4h 00m

Chicago Midway

Sat 1/31

7:40 pm-10:10 pm

Nonstop4h 30m

$157

San DiegoChicago

SAN - ORD

SANORD

San Diego

Wed 1/21

5:10 pm-11:37 pm

Nonstop4h 27m

Chicago O'Hare Intl

Wed 1/28

3:44 pm-6:26 pm

Nonstop4h 42m

$157

San DiegoChicago

SAN - ORD

SANORD

San Diego

Mon 1/12

8:00 am-2:29 pm

Nonstop4h 29m

Chicago O'Hare Intl

Thu 1/22

9:00 am-5:03 pm

1 stop10h 03m

$159

San DiegoChicago

SAN - ORD

SANORD

San Diego

Wed 2/18

7:50 pm-5:12 am

1 stop7h 22m

Chicago O'Hare Intl

Wed 2/25

8:47 am-11:38 am

Nonstop4h 51m

$161

San DiegoChicago

SAN - ORD

SANORD

San Diego

Fri 1/9

6:36 am-12:42 am

2 stops16h 06m

Chicago O'Hare Intl

Sun 1/11

10:07 pm-7:37 pm

1 stop23h 30m

$162

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Fri 1/16

6:25 am-7:54 pm

1 stop11h 29m

Chicago Midway

Sun 1/18

8:19 pm-10:13 am

1 stop15h 54m

$162

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Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from San Diego to Chicago

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

Prices

Airlines

Delays

Other information

What is the cheapest month to fly to Chicago?

The month of October is, on average, the cheapest month to fly to Chicago from San Diego, with most prices found around $237. If you’re not able to fly to Chicago in October, then September is your next best option. Flight prices from San Diego to Chicago during September average around $240.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $399. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from San Diego to Chicago for around $578.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from San Diego to Chicago during this time can be as low as $266. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $473.

What is the cheapest San Diego to Chicago flight route?

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

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from San Diego when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $342 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from San Diego for as low as $258 on momondo.

What cabin class options are available on San Diego to Chicago flights?

There are 4 cabin classes available to choose from on San Diego to Chicago 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 flights?

You could potentially save up to 11% on your flight if you consider stops on a San Diego to Chicago flight.

How have San Diego to Chicago flight prices changed over time?

As of November 2025, prices for San Diego to Chicago flights are approximately 19% more expensive when compared to flights at the same time last year.

When to book flights from San Diego to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from San Diego to Chicago according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap San Diego to Chicago (SAN to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from San Diego to Chicago

Best Price Found	$124
Fastest flight time	3h 50m
Direct flights	Every day
Airports in Chicago	2 airports

The best one-way flight to Chicago from San Diego in the past 72 hours is $124. The best round-trip flight deal from San Diego to Chicago found on momondo in the last 72 hours is $240.

The fastest flight from San Diego to Chicago takes 3h 50m

Direct flights go from San Diego to Chicago every day.

There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

Search flight deals

How far is San Diego to Chicago by plane?
The straight-line distance from San Diego to Chicago is 1730.3 mi. Typically, this will take 3h 50m by plane in normal conditions.
When did momondo last update prices for flights from San Diego Airport to Chicago?
Prices for flights from San Diego Airport to Chicago are refreshed on a daily basis.
How many operators does momondo search for flights from San Diego Airport to Chicago?
As of November 2025, there are 8 operators available to choose from for flights from San Diego Airport to Chicago.
How old do you have to be to fly from San Diego Airport to Chicago?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from San Diego Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from San Diego to Chicago?
Based on momondo bookings for flights between San Diego and Chicago, the leading plane model is Boeing 737-800, making up 26.94% of the total bookings. Other popular models include Airbus A321neo with 17.35%, Boeing 737 MAX 9 with 13.13%, and Boeing 737-800 Passenger/BBJ2 (winglets) with 12.87%.
What is the most popular airline from San Diego to Chicago?
Based on momondo bookings for flights between San Diego and Chicago, the leading airline is American Airlines, making up 31% of the total bookings. Other popular airlines include Frontier with 19%, United Airlines with 19%, and Southwest with 14%.

Best airlines flying from San Diego to Chicago

Compare and see reviews for airlines that fly from San Diego to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Spirit Airlines	PriceFrom $99	Free Cancellation	Rating 6.3 8,158 reviews	Search Spirit Airlines flights
Frontier	PriceFrom $110	Free Cancellation	Rating 5.8 3,099 reviews	Search Frontier flights
Alaska Airlines	PriceFrom $139	Free Cancellation	Rating 8.0 11,354 reviews	Search Alaska Airlines flights
Hawaiian Airlines	PriceFrom $139	Free Cancellation	Rating 7.8 2,814 reviews	Search Hawaiian Airlines flights
American Airlines	PriceFrom $167	Free Cancellation	Rating 7.2 11,038 reviews	Search American Airlines flights
United Airlines	PriceFrom $193	Free Cancellation	Rating 7.4 9,046 reviews	Search United Airlines flights
Southwest	PriceFrom $205	Free Cancellation	Rating 8.0 4,254 reviews	Search Southwest flights
Delta	PriceFrom $256	Free Cancellation	Rating 7.9 7,998 reviews	Search Delta flights

Alaska Airlines Flights From San Diego to Chicago
Alaska Airlines flight deals from San Diego to Chicago start from $139 round-trip. Over the 16 Alaska Airlines flights for this route in a normal week, average airfare is usually $261 round-trip - but some users have found much cheaper deals with momondo.
Southwest Flights From San Diego to Chicago
Southwest (8.0/10 from 4,254 reviews) operates around 21 flights from San Diego to Chicago in any given week. The average Southwest airfare for this route is around $398, with deals from around $205 rare but found on momondo. Referenced prices are for round-trip San Diego to Chicago flight searches in the last 72 hours.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

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

Finding the right flight to Chicago from San Diego is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

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?

Once you have performed a search for San Diego to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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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Cheap flights from San Diego to Chicago from $84

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 12/16. 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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American Airlines flights from San Diego to Chicago

Our best American Airlines deals on San Diego to Chicago flight tickets

Frontier flights from San Diego to Chicago

Our best Frontier deals on San Diego to Chicago flight tickets

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Use the filters below to find and compare flights from San Diego to Chicago that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from San Diego to Chicago

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 cheapest month to fly to Chicago?

The month of October is, on average, the cheapest month to fly to Chicago from San Diego, with most prices found around $237. If you’re not able to fly to Chicago in October, then September is your next best option. Flight prices from San Diego to Chicago during September average around $240.

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from San Diego to Chicago during this time can be as low as $266. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $473.

What is the cheapest San Diego to Chicago flight route?

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

How far in advance should I book a flight to Chicago?

What cabin class options are available on San Diego to Chicago flights?

There are 4 cabin classes available to choose from on San Diego to Chicago 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 flights?

You could potentially save up to 11% on your flight if you consider stops on a San Diego to Chicago flight.

How have San Diego to Chicago flight prices changed over time?

As of November 2025, prices for San Diego to Chicago flights are approximately 19% more expensive when compared to flights at the same time last year.

What is the cheapest airline that flies from San Diego to Chicago?

United Airlines, Southwest, and Alaska Airlines are the most popular carriers operating from San Diego to Chicago

What airlines fly to Chicago?

How often are flights from San Diego to Chicago delayed?

Historically, on average around 9% of flights between San Diego and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 171 minutes.

What is the most punctual flight time for San Diego to Chicago flights?

Generally, flights departing at night tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

What day of the week experiences the fewest flight delays on this route?

Monday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

Which airline has the best punctuality record on San Diego to Chicago flights?

According to our data, Air Canada have had the least number of delays on this route over the last 12 months; with no flights being classified as delayed.

How many flights depart from San Diego to Chicago on average per day?

30 flights are operational daily from San Diego to Chicago as of November 2025. The most popular departure time for this route is 6:00AM, with 60% of flights per day taking off at noon.

How many flights depart from San Diego to Chicago on average per week?

The number of flights available between San Diego and Chicago is 213 per week as of November 2025. The most frequent departure day is Mon, with 21% of weekly flights leaving on this day.

When to book flights from San Diego to Chicago

Cheap San Diego to Chicago (SAN to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from San Diego to Chicago

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

How far is San Diego to Chicago by plane?

When did momondo last update prices for flights from San Diego Airport to Chicago?

How many operators does momondo search for flights from San Diego Airport to Chicago?

How old do you have to be to fly from San Diego Airport to Chicago?

What documentation or ID do you need to fly to Chicago?

What is the most popular plane model from San Diego to Chicago?

What is the most popular airline from San Diego to Chicago?

Best airlines flying from San Diego to Chicago

Compare and see reviews for airlines that fly from San Diego to Chicago with momondo

Alaska Airlines Flights From San Diego to Chicago

Southwest Flights From San Diego to Chicago

Traveling to a place near Chicago?

Why use momondo?

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

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

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

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

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down