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

The number of flights available between San Diego and Chicago is 313 per week as of October 2025. The most frequent departure day is Mon, with 16% of weekly flights leaving on this day.

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.

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

Frontier, American 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 day?

44 flights are operational daily from San Diego to Chicago as of October 2025. The most popular departure time for this route is 6:00AM, with 52% of flights per day taking off at noon.

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 October 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.

$78 Cheap Flights from San Diego to Chicago in 2025/26

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Cheap round-trip flights

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8:00 am - 1:54 pmSAN-ORD

3h 54mnonstop

8:49 pm - 11:13 pmORD-SAN

4h 24mnonstop

$152Alaska Airlines

Find Deal

Wed, Nov 19 - Wed, Nov 26

5:53 pm - 11:50 pmSAN-ORD

3h 57mnonstop

3:05 pm - 5:33 pmORD-SAN

4h 28mnonstop

$153Alaska Airlines

Find Deal

Wed, Dec 3 - Sat, Dec 6

8:30 am - 9:48 pmSAN-ORD

11h 18m1 stop

10:43 pm - 8:24 pmORD-SAN

47h 41m2 stops

$154Frontier

Find Deal

Fri, Nov 14 - Mon, Nov 17

2:28 pm - 8:36 pmSAN-MDW

28h 08m1 stop

2:45 pm - 12:01 amMDW-SAN

11h 16m1 stop

$154Frontier

Find Deal

Wed, Dec 3 - Thu, Dec 11

6:25 am - 12:25 pmSAN-MDW

4h 00mnonstop

8:15 am - 10:50 amMDW-SAN

4h 35mnonstop

$157Southwest

Find Deal

Wed, Jan 28 - Wed, Feb 4

6:41 am - 3:39 pmSAN-ORD

6h 58m1 stop

8:59 pm - 11:19 pmORD-SAN

4h 20mnonstop

$162Multiple Airlines

Find Deal

Wed, Nov 12 - Wed, Nov 19

6:41 am - 3:39 pmSAN-ORD

6h 58m1 stop

8:59 pm - 11:19 pmORD-SAN

4h 20mnonstop

$164Multiple Airlines

Find Deal

Wed, Nov 5 - Sat, Nov 8

7:30 am - 4:45 pmSAN-MDW

7h 15m1 stop

8:15 am - 10:50 amMDW-SAN

4h 35mnonstop

$167Southwest

Find Deal

Wed, Jan 28 - Wed, Feb 4

5:15 pm - 11:24 pmSAN-ORD

4h 09mnonstop

4:20 pm - 6:52 pmORD-SAN

4h 32mnonstop

$185United Airlines

Find Deal

Mon, Nov 3 - Sat, Nov 8

4:01 pm - 12:59 amSAN-ORD

6h 58m1 stop

4:20 pm - 6:52 pmORD-SAN

4h 32mnonstop

$195United Airlines

Find Deal

Mon, Nov 3 - Sat, Nov 8

Alaska Airlines flights from San Diego to Chicago

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

Alaska Airlines

Nov 19

SAN8:00 amSan Diego

3h 54m

ORD1:54 pmChicago O'Hare Intl

Nov 26

ORD8:49 pmChicago O'Hare Intl

4h 24m

SAN11:13 pmSan Diego

$152

Find similar

Alaska Airlines

Dec 3

SAN5:53 pmSan Diego

3h 57m

ORD11:50 pmChicago O'Hare Intl

Dec 6

ORD3:05 pmChicago O'Hare Intl

4h 28m

SAN5:33 pmSan Diego

$153

Find similar

Alaska Airlines

Nov 12

SAN8:00 amSan Diego

3h 54m

ORD1:54 pmChicago O'Hare Intl

Nov 19

ORD9:20 amChicago O'Hare Intl

4h 25m

SAN11:45 amSan Diego

$155

Find similar

Frontier flights from San Diego to Chicago

Our best Frontier deals on San Diego to Chicago flight tickets

Frontier

Oct 29

SAN2:24 pmSan Diego

7h 48m

1 stop

ORD12:12 amChicago O'Hare Intl

Oct 30

ORD6:00 amChicago O'Hare Intl

7h 17m

1 stop

SAN11:17 amSan Diego

$152

Find similar

Frontier

Nov 14

SAN8:30 amSan Diego

11h 18m

1 stop

ORD9:48 pmChicago O'Hare Intl

Nov 17

ORD10:43 pmChicago O'Hare Intl

47h 41m

2 stops

SAN8:24 pmSan Diego

$154

Find similar

Frontier

Nov 13

SAN6:41 amSan Diego

13h 22m

2 stops

MDW10:03 pmChicago Midway

Nov 15

MDW2:57 pmChicago Midway

7h 27m

1 stop

SAN8:24 pmSan Diego

$156

Find similar

Fly from

Fly to

Route

Depart

Return

Price

San DiegoChicago

SAN - ORD

SANORD

San Diego

Wed 11/19

8:00 am-1:54 pm

Nonstop3h 54m

Chicago O'Hare Intl

Wed 11/26

8:49 pm-11:13 pm

Nonstop4h 24m

$152

San DiegoChicago

SAN - ORD

SANORD

San Diego

Wed 12/3

5:53 pm-11:50 pm

Nonstop3h 57m

Chicago O'Hare Intl

Sat 12/6

3:05 pm-5:33 pm

Nonstop4h 28m

$153

San DiegoChicago

SAN - ORD

SANORD

San Diego

Fri 11/14

8:30 am-9:48 pm

1 stop11h 18m

Chicago O'Hare Intl

Mon 11/17

10:43 pm-8:24 pm

2 stops47h 41m

$154

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Wed 12/3

2:28 pm-8:36 pm

1 stop28h 08m

Chicago Midway

Thu 12/11

2:45 pm-12:01 am

1 stop11h 16m

$154

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Wed 1/28

6:25 am-12:25 pm

Nonstop4h 00m

Chicago Midway

Wed 2/4

8:15 am-10:50 am

Nonstop4h 35m

$157

San DiegoChicago

SAN - ORD

SANORD

San Diego

Wed 11/12

6:41 am-3:39 pm

1 stop6h 58m

Chicago O'Hare Intl

Wed 11/19

8:59 pm-11:19 pm

Nonstop4h 20m

$162

San DiegoChicago

SAN - ORD

SANORD

San Diego

Wed 11/5

6:41 am-3:39 pm

1 stop6h 58m

Chicago O'Hare Intl

Sat 11/8

8:59 pm-11:19 pm

Nonstop4h 20m

$164

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Wed 1/28

7:30 am-4:45 pm

1 stop7h 15m

Chicago Midway

Wed 2/4

8:15 am-10:50 am

Nonstop4h 35m

$167

San DiegoChicago

SAN - ORD

SANORD

San Diego

Mon 11/3

5:15 pm-11:24 pm

Nonstop4h 09m

Chicago O'Hare Intl

Sat 11/8

4:20 pm-6:52 pm

Nonstop4h 32m

$185

San DiegoChicago

SAN - ORD

SANORD

San Diego

Mon 11/3

4:01 pm-12:59 am

1 stop6h 58m

Chicago O'Hare Intl

Sat 11/8

4:20 pm-6:52 pm

Nonstop4h 32m

$195

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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 typical price of a round-trip flight between San Diego and Chicago?

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from San Diego, with most prices found around $240. If you’re not able to fly to Chicago in September, then August is your next best option. Flight prices from San Diego to Chicago during August average around $251.

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 $416. 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 $587.

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 $269. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $493.

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 $363 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 10% 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 October 2025, prices for San Diego to Chicago flights are approximately 17% 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	$132
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 $132. The best round-trip flight deal from San Diego to Chicago found on momondo in the last 72 hours is $273.

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 54m 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 October 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 30.66% of the total bookings. Other popular models include Airbus A321neo with 14.87%, Boeing 737-900 with 10.48%, and Boeing 737 MAX 9 with 9.10%.
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 33% of the total bookings. Other popular airlines include Frontier with 22%, United Airlines with 20%, and Southwest with 15%.

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
Frontier	PriceFrom $118	Free Cancellation	Rating 5.8 3,135 reviews	Search Frontier flights
Spirit Airlines	PriceFrom $126	Free Cancellation	Rating 6.3 8,097 reviews	Search Spirit Airlines flights
Hawaiian Airlines	PriceFrom $139	Free Cancellation	Rating 7.8 2,779 reviews	Search Hawaiian Airlines flights
Alaska Airlines	PriceFrom $147	Free Cancellation	Rating 8.0 11,082 reviews	Search Alaska Airlines flights
American Airlines	PriceFrom $169	Free Cancellation	Rating 7.2 11,044 reviews	Search American Airlines flights
United Airlines	PriceFrom $207	Free Cancellation	Rating 7.4 8,977 reviews	Search United Airlines flights
Southwest	PriceFrom $216	Free Cancellation	Rating 8.0 4,238 reviews	Search Southwest flights
Delta	PriceFrom $256	Free Cancellation	Rating 7.9 7,977 reviews	Search Delta flights

Alaska Airlines Flights From San Diego to Chicago
Alaska Airlines flight deals from San Diego to Chicago start from $147 round-trip. Over the 18 Alaska Airlines flights for this route in a normal week, average airfare is usually $267 round-trip - but some users have found much cheaper deals with momondo.
Southwest Flights From San Diego to Chicago
Southwest (8.0/10 from 4,239 reviews) operates around 15 flights from San Diego to Chicago in any given week. The average Southwest airfare for this route is around $417, with deals from around $216 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.

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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Fri 11/14

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Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

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Flights to Washington, D.C.from $50

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Flights to Denverfrom $54

Cheap flights from San Diego to Chicago from $78

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 12/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

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Find the cheapest flights from San Diego to Chicago

Cheap round-trip flights

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Cheap last minute flights

Cheap direct flights

Alaska Airlines flights from San Diego to Chicago

Our best Alaska 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

momondo Fare Finder

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 typical price of a round-trip flight between San Diego and Chicago?

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from San Diego, with most prices found around $240. If you’re not able to fly to Chicago in September, then August is your next best option. Flight prices from San Diego to Chicago during August average around $251.

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 $269. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $493.

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 10% 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 October 2025, prices for San Diego to Chicago flights are approximately 17% more expensive when compared to flights at the same time last year.

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

Frontier, American 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?

44 flights are operational daily from San Diego to Chicago as of October 2025. The most popular departure time for this route is 6:00AM, with 52% 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 313 per week as of October 2025. The most frequent departure day is Mon, with 16% 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