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 50% 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.

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

49 flights are operational daily from San Diego to Chicago as of August 2025. The most popular departure time for this route is 6:00AM, with 48% of flights per day taking off at noon.

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

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

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

The number of flights available between San Diego and Chicago is 346 per week as of August 2025. The most frequent departure day is Fri, with 17% of weekly flights leaving on this day.

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 August 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.

$51 Cheap Flights from San Diego to Chicago in 2025

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Find the cheapest flights from San Diego to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

1:35 pm - 9:32 pmSAN-ORD

5h 57m1 stop

7:55 am - 10:30 amORD-SAN

4h 35mnonstop

$149

Find Deal

Tue, Sep 9 - Mon, Sep 22

6:35 am - 11:59 pmSAN-ORD

15h 24m1 stop

7:20 am - 10:24 pmORD-SAN

17h 04m1 stop

$150Frontier

Find Deal

Thu, Sep 11 - Tue, Sep 16

5:19 pm - 11:59 pmSAN-ORD

4h 40mnonstop

7:15 am - 9:37 amORD-SAN

4h 22mnonstop

$151

Find Deal

Wed, Oct 15 - Mon, Oct 20

2:31 pm - 10:40 pmSAN-ORD

6h 09m1 stop

6:00 am - 11:09 amORD-SAN

7h 09m1 stop

$152Frontier

Find Deal

Fri, Sep 12 - Mon, Sep 15

7:47 pm - 11:51 amSAN-ORD

14h 04m1 stop

6:05 pm - 10:26 pmORD-SAN

6h 21m1 stop

$161Spirit Airlines

Find Deal

Fri, Sep 5 - Mon, Sep 8

2:11 pm - 8:25 pmSAN-ORD

4h 14mnonstop

4:10 pm - 6:30 pmORD-SAN

4h 20mnonstop

$168United Airlines

Find Deal

Thu, Sep 25 - Sat, Sep 27

4:05 pm - 10:00 pmSAN-MDW

3h 55mnonstop

8:50 pm - 11:05 pmMDW-SAN

4h 15mnonstop

$168Southwest

Find Deal

Tue, Sep 23 - Fri, Sep 26

6:55 am - 12:55 pmSAN-MDW

4h 00mnonstop

7:25 pm - 9:35 pmMDW-SAN

4h 10mnonstop

$178Southwest

Find Deal

Mon, Sep 15 - Sat, Sep 20

2:55 pm - 9:12 pmSAN-ORD

4h 17mnonstop

7:00 am - 9:18 amORD-SAN

4h 18mnonstop

$184American Airlines

Find Deal

Wed, Sep 10 - Wed, Sep 17

7:47 pm - 11:51 amSAN-ORD

14h 04m1 stop

8:01 pm - 7:29 amORD-SAN

13h 28m1 stop

$191Spirit Airlines

Find Deal

Fri, Sep 5 - Sun, Sep 7

Hawaiian Airlines flights from San Diego to Chicago

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

Hawaiian Airlines

Oct 8

SAN8:10 amSan Diego

4h 40m

ORD2:50 pmChicago O'Hare Intl

Oct 8

ORD3:50 pmChicago O'Hare Intl

5h 00m

SAN6:50 pmSan Diego

$185

Find similar

Hawaiian Airlines

Oct 31

SAN5:49 pmSan Diego

4h 10m

ORD11:59 pmChicago O'Hare Intl

Nov 2

ORD9:20 amChicago O'Hare Intl

4h 25m

SAN11:45 amSan Diego

$195

Find similar

Hawaiian Airlines

Oct 31

SAN12:45 pmSan Diego

4h 14m

ORD6:59 pmChicago O'Hare Intl

Nov 3

ORD9:20 amChicago O'Hare Intl

4h 25m

SAN11:45 amSan Diego

$197

Find similar

Frontier flights from San Diego to Chicago

Our best Frontier deals on San Diego to Chicago flight tickets

Frontier

Sep 11

SAN6:35 amSan Diego

15h 24m

1 stop

ORD11:59 pmChicago O'Hare Intl

Sep 16

ORD7:20 amChicago O'Hare Intl

17h 04m

1 stop

SAN10:24 pmSan Diego

$150

Find similar

Frontier

Sep 12

SAN2:31 pmSan Diego

6h 09m

1 stop

ORD10:40 pmChicago O'Hare Intl

Sep 15

ORD6:00 amChicago O'Hare Intl

7h 09m

1 stop

SAN11:09 amSan Diego

$152

Find similar

Frontier

Sep 4

SAN6:35 amSan Diego

15h 24m

1 stop

ORD11:59 pmChicago O'Hare Intl

Sep 7

ORD7:55 amChicago O'Hare Intl

4h 35m

SAN10:30 amSan Diego

$153

Find similar

Fly from

Fly to

Route

Depart

Return

Price

San DiegoChicago

SAN - ORD

SANORD

San Diego

Tue 9/9

1:35 pm-9:32 pm

1 stop5h 57m

Chicago O'Hare Intl

Mon 9/22

7:55 am-10:30 am

Nonstop4h 35m

$149

San DiegoChicago

SAN - ORD

SANORD

San Diego

Thu 9/11

6:35 am-11:59 pm

1 stop15h 24m

Chicago O'Hare Intl

Tue 9/16

7:20 am-10:24 pm

1 stop17h 04m

$150

San DiegoChicago

SAN - ORD

SANORD

San Diego

Wed 10/15

5:19 pm-11:59 pm

Nonstop4h 40m

Chicago O'Hare Intl

Mon 10/20

7:15 am-9:37 am

Nonstop4h 22m

$151

San DiegoChicago

SAN - ORD

SANORD

San Diego

Fri 9/12

2:31 pm-10:40 pm

1 stop6h 09m

Chicago O'Hare Intl

Mon 9/15

6:00 am-11:09 am

1 stop7h 09m

$152

San DiegoChicago

SAN - ORD

SANORD

San Diego

Fri 9/5

7:47 pm-11:51 am

1 stop14h 04m

Chicago O'Hare Intl

Mon 9/8

6:05 pm-10:26 pm

1 stop6h 21m

$161

San DiegoChicago

SAN - ORD

SANORD

San Diego

Thu 9/25

2:11 pm-8:25 pm

Nonstop4h 14m

Chicago O'Hare Intl

Sat 9/27

4:10 pm-6:30 pm

Nonstop4h 20m

$168

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Tue 9/23

4:05 pm-10:00 pm

Nonstop3h 55m

Chicago Midway

Fri 9/26

8:50 pm-11:05 pm

Nonstop4h 15m

$168

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Mon 9/15

6:55 am-12:55 pm

Nonstop4h 00m

Chicago Midway

Sat 9/20

7:25 pm-9:35 pm

Nonstop4h 10m

$178

San DiegoChicago

SAN - ORD

SANORD

San Diego

Wed 9/10

2:55 pm-9:12 pm

Nonstop4h 17m

Chicago O'Hare Intl

Wed 9/17

7:00 am-9:18 am

Nonstop4h 18m

$184

San DiegoChicago

SAN - ORD

SANORD

San Diego

Fri 9/5

7:47 pm-11:51 am

1 stop14h 04m

Chicago O'Hare Intl

Sun 9/7

8:01 pm-7:29 am

1 stop13h 28m

$191

Flights are sorted by cheapest round-trip flights first.

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

Other information

What is the cheapest month to fly to Chicago?

The month of August is, on average, the cheapest month to fly to Chicago from San Diego, with most prices found around $261. If you’re not able to fly to Chicago in August, then September is your next best option. Flight prices from San Diego to Chicago during September average around $277.

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 $430. 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 $588.

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 $287. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $515.

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 $374 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 $249 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?

No. A direct flight is the cheapest option for a flight between San Diego to Chicago.

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

As of August 2025, prices for San Diego to Chicago flights are approximately 16% cheaper 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	$149
Fastest flight time	3h 54m
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 $149. The best round-trip flight deal from San Diego to Chicago found on momondo in the last 72 hours is $197.

The fastest flight from San Diego to Chicago takes 3h 54m

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 55m 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 August 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 32.66% of the total bookings. Other popular models include Airbus A321neo with 12.60%, Boeing 737-900 with 10.97%, and Airbus A321-100/200 with 9.68%.
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 32% of the total bookings. Other popular airlines include Frontier with 24%, United Airlines with 20%, and Southwest with 16%.

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 $98	Free Cancellation	Rating 6.3 8,029 reviews	Search Spirit Airlines flights
Frontier	PriceFrom $116	Free Cancellation	Rating 5.8 3,201 reviews	Search Frontier flights
American Airlines	PriceFrom $175	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Alaska Airlines	PriceFrom $184	Free Cancellation	Rating 8.0 10,000 reviews	Search Alaska Airlines flights
United Airlines	PriceFrom $225	Free Cancellation	Rating 7.4 8,940 reviews	Search United Airlines flights
Southwest	PriceFrom $236	Free Cancellation	Rating 8.0 4,243 reviews	Search Southwest flights
Delta	PriceFrom $267	Free Cancellation	Rating 7.9 7,981 reviews	Search Delta flights

Alaska Airlines Flights From San Diego to Chicago
Alaska Airlines flight deals from San Diego to Chicago start from $184 round-trip. Over the 31 Alaska Airlines flights for this route in a normal week, average airfare is usually $537 round-trip - but some users have found much cheaper deals with momondo.
Southwest Flights From San Diego to Chicago
Southwest (8.0/10 from 4,243 reviews) operates around 27 flights from San Diego to Chicago in any given week. The average Southwest airfare for this route is around $431, with deals from around $236 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

Lansing

Portage

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.

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.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

Popular cities in the United States

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Flights to Washington, D.C.from $37

Flights to Bostonfrom $58

Flights to Atlantafrom $37

Flights to Dallasfrom $38

Flights to Seattlefrom $45

Flights to Denverfrom $37

Cheap flights from San Diego to Chicago from $79

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 9/16. 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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Big names and deals

Filter for what you want

Filter for what you want

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Find the cheapest flights from San Diego to Chicago

Cheap round-trip flights

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Hawaiian Airlines flights from San Diego to Chicago

Our best Hawaiian 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 August is, on average, the cheapest month to fly to Chicago from San Diego, with most prices found around $261. If you’re not able to fly to Chicago in August, then September is your next best option. Flight prices from San Diego to Chicago during September average around $277.

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 $287. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $515.

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?

No. A direct flight is the cheapest option for a flight between San Diego to Chicago.

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

As of August 2025, prices for San Diego to Chicago flights are approximately 16% cheaper when compared to flights at the same time last year.

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

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

What airlines fly to Chicago?

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

49 flights are operational daily from San Diego to Chicago as of August 2025. The most popular departure time for this route is 6:00AM, with 48% 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 346 per week as of August 2025. The most frequent departure day is Fri, with 17% 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

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago