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Cheap flights from San Diego to Chicago from $54

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 1/23. 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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Find the cheapest flights from San Diego to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from San Diego to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from San Diego to Chicago.

Cheap last minute flights

Planning a quick getaway from San Diego to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from San Diego to Chicago

Find recent round-trip train or bus tickets from San Diego to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
10:29 am - 8:51 pmSAN-ORD
8h 22m1 stop
6:32 pm - 12:20 amORD-SAN
7h 48m1 stop
$105Frontier
Find Deal
Thu, Feb 13 - Sat, Feb 15
9:56 pm - 5:31 amSAN-MDW
5h 35m1 stop
7:05 am - 11:48 amMDW-SAN
6h 43m1 stop
$106Frontier
Find Deal
Sat, Feb 22 - Tue, Feb 25
6:15 am - 9:52 pmSAN-ORD
13h 37m1 stop
1:39 pm - 10:18 pmORD-SAN
10h 39m1 stop
$161Spirit Airlines
Find Deal
Sat, Jan 25 - Fri, Jan 31
7:26 pm - 5:31 amSAN-ORD
8h 05m1 stop
1:39 pm - 3:26 pmORD-SAN
27h 47m1 stop
$162Spirit Airlines
Find Deal
Sat, Jan 18 - Tue, Jan 21
2:35 pm - 8:25 pmSAN-MDW
3h 50mnonstop
4:15 pm - 6:45 pmMDW-SAN
4h 30mnonstop
$237Southwest
Find Deal
Sat, Jan 18 - Tue, Jan 21
2:35 pm - 8:25 pmSAN-MDW
3h 50mnonstop
3:20 pm - 5:55 pmMDW-SAN
4h 35mnonstop
$274Southwest
Find Deal
Sat, Jan 18 - Sat, Jan 25
6:40 am - 12:48 pmSAN-ORD
4h 08mnonstop
5:45 pm - 8:10 pmORD-SAN
4h 25mnonstop
$282American Airlines
Find Deal
Sat, Jan 18 - Tue, Jan 21
2:14 pm - 8:25 pmSAN-ORD
4h 11mnonstop
1:15 pm - 3:48 pmORD-SAN
4h 33mnonstop
$312United Airlines
Find Deal
Tue, Jan 21 - Tue, Jan 28
8:51 pm - 5:54 amSAN-ORD
7h 03m1 stop
8:50 am - 11:28 amORD-SAN
4h 38mnonstop
$322United Airlines
Find Deal
Tue, Jan 21 - Tue, Jan 28
1:28 pm - 7:38 pmSAN-ORD
4h 10mnonstop
5:45 pm - 8:10 pmORD-SAN
4h 25mnonstop
$337American Airlines
Find Deal
Thu, Jan 16 - Sat, Jan 18
1:47 pm - 11:44 pmSAN-ORD
7h 57m1 stop
$54Frontier
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Thu, Jan 23
2:32 pm - 12:13 amSAN-MDW
7h 41m1 stop
$54Frontier
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Wed, Jan 8
7:41 pm - 6:07 amSAN-ORD
8h 26m1 stop
$73Spirit Airlines
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Fri, Feb 21
7:26 pm - 5:31 amSAN-ORD
8h 05m1 stop
$76Spirit Airlines
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Sat, Jan 25
7:00 am - 1:11 pmSAN-ORD
4h 11mnonstop
$119United Airlines
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Sat, Jan 25
4:50 pm - 10:40 pmSAN-MDW
3h 50mnonstop
$119Southwest
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Tue, Jan 21
2:35 pm - 8:25 pmSAN-MDW
3h 50mnonstop
$156Southwest
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Sat, Jan 25
10:39 pm - 4:42 amSAN-ORD
4h 03mnonstop
$165American Airlines
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Tue, Dec 31
10:39 am - 4:48 pmSAN-ORD
4h 09mnonstop
$194United Airlines
Find Deal
Tue, Jan 28
10:37 pm - 4:45 amSAN-ORD
4h 08mnonstop
$271American Airlines
Find Deal
Sun, Mar 30
9:41 pm - 9:49 amSAN-MDW
10h 08m1 stop
6:25 am - 2:04 pmMDW-SAN
9h 39m1 stop
$284Frontier
Find Deal
Sat, Dec 28 - Sat, Jan 4
9:41 pm - 9:49 amSAN-MDW
10h 08m1 stop
8:27 pm - 10:07 amMDW-SAN
15h 40m1 stop
$286Frontier
Find Deal
Sat, Dec 28 - Fri, Jan 3
7:16 pm - 5:30 amSAN-ORD
8h 14m1 stop
9:54 pm - 5:11 pmORD-SAN
21h 17m1 stop
$470Spirit Airlines
Find Deal
Wed, Dec 25 - Sun, Dec 29
6:06 pm - 5:30 amSAN-ORD
9h 24m1 stop
8:55 pm - 5:11 pmORD-SAN
22h 16m2 stops
$490Spirit Airlines
Find Deal
Fri, Dec 27 - Fri, Jan 3
11:00 am - 9:42 amSAN-ORD
20h 42m2 stops
1:15 pm - 3:48 pmORD-SAN
4h 33mnonstop
$604United Airlines
Find Deal
Wed, Dec 25 - Thu, Dec 26
9:55 pm - 11:01 amSAN-ORD
11h 06m1 stop
2:56 pm - 5:25 pmORD-SAN
4h 29mnonstop
$610American Airlines
Find Deal
Wed, Dec 25 - Thu, Dec 26
4:55 pm - 10:58 pmSAN-ORD
4h 03mnonstop
7:10 am - 9:47 amORD-SAN
4h 37mnonstop
$668United Airlines
Find Deal
Wed, Dec 25 - Wed, Jan 1
10:52 am - 9:28 pmSAN-ORD
8h 36m1 stop
9:07 pm - 11:40 pmORD-SAN
4h 33mnonstop
$678American Airlines
Find Deal
Wed, Dec 25 - Tue, Dec 31
6:55 pm - 12:50 amSAN-MDW
3h 55mnonstop
8:25 pm - 10:50 pmMDW-SAN
4h 25mnonstop
$877Southwest
Find Deal
Fri, Dec 27 - Fri, Jan 3
8:15 am - 4:35 pmSAN-MDW
6h 20m1 stop
8:25 pm - 10:50 pmMDW-SAN
4h 25mnonstop
$882Southwest
Find Deal
Sat, Dec 28 - Fri, Jan 3
6:40 am - 12:31 pmSAN-ORD
3h 51mnonstop
10:06 am - 12:36 pmORD-SAN
4h 30mnonstop
$237American Airlines
Find Deal
Sat, Feb 15 - Sat, Feb 22
2:35 pm - 8:25 pmSAN-MDW
3h 50mnonstop
4:15 pm - 6:45 pmMDW-SAN
4h 30mnonstop
$237Southwest
Find Deal
Sat, Jan 18 - Tue, Jan 21
2:35 pm - 8:25 pmSAN-MDW
3h 50mnonstop
3:20 pm - 5:55 pmMDW-SAN
4h 35mnonstop
$274Southwest
Find Deal
Sat, Jan 18 - Sat, Jan 25
6:40 am - 12:48 pmSAN-ORD
4h 08mnonstop
5:45 pm - 8:10 pmORD-SAN
4h 25mnonstop
$282American Airlines
Find Deal
Sat, Jan 18 - Tue, Jan 21
6:40 am - 12:48 pmSAN-ORD
4h 08mnonstop
5:45 pm - 8:10 pmORD-SAN
4h 25mnonstop
$312American Airlines
Find Deal
Wed, Jan 15 - Sat, Jan 18
4:55 pm - 10:45 pmSAN-MDW
3h 50mnonstop
4:15 pm - 6:45 pmMDW-SAN
4h 30mnonstop
$312Southwest
Find Deal
Sat, Feb 22 - Tue, Feb 25
7:00 am - 1:11 pmSAN-ORD
4h 11mnonstop
1:15 pm - 3:48 pmORD-SAN
4h 33mnonstop
$327United Airlines
Find Deal
Sat, Jan 18 - Sat, Jan 25
2:23 pm - 8:25 pmSAN-ORD
4h 02mnonstop
7:45 pm - 10:30 pmORD-SAN
4h 45mnonstop
$354United Airlines
Find Deal
Thu, Feb 13 - Sat, Feb 15
1:28 pm - 7:38 pmSAN-ORD
4h 10mnonstop
5:45 pm - 8:10 pmORD-SAN
4h 25mnonstop
$648Alaska Airlines
Find Deal
Tue, Jan 28 - Wed, Jan 29
6:35 am - 12:51 pmSAN-ORD
4h 16mnonstop
5:45 pm - 8:10 pmORD-SAN
4h 25mnonstop
$1,417Alaska Airlines
Find Deal
Mon, Jan 6 - Thu, Jan 9

Frontier flights from San Diego to Chicago

Our best Frontier deals on San Diego to Chicago flight tickets
Frontier
Feb 13
SAN10:29 amSan Diego
8h 22m
1 stop
ORD8:51 pmChicago O'Hare Intl
Feb 15
ORD6:32 pmChicago O'Hare Intl
7h 48m
1 stop
SAN12:20 amSan Diego
Frontier
Feb 22
SAN9:56 pmSan Diego
5h 35m
1 stop
MDW5:31 amChicago Midway
Feb 25
MDW7:05 amChicago Midway
6h 43m
1 stop
SAN11:48 amSan Diego
Frontier
Feb 15
SAN12:05 pmSan Diego
10h 56m
1 stop
ORD1:01 amChicago O'Hare Intl
Feb 22
ORD7:59 pmChicago O'Hare Intl
19h 29m
1 stop
SAN1:28 pmSan Diego

American Airlines flights from San Diego to Chicago

Our best American Airlines deals on San Diego to Chicago flight tickets
American Airlines
Jan 18
SAN6:40 amSan Diego
4h 08m
ORD12:48 pmChicago O'Hare Intl
Jan 21
ORD5:45 pmChicago O'Hare Intl
4h 25m
SAN8:10 pmSan Diego
American Airlines
Jan 16
SAN1:28 pmSan Diego
4h 10m
ORD7:38 pmChicago O'Hare Intl
Jan 18
ORD5:45 pmChicago O'Hare Intl
4h 25m
SAN8:10 pmSan Diego
American Airlines
Jan 25
SAN6:40 amSan Diego
4h 08m
ORD12:48 pmChicago O'Hare Intl
Feb 2
ORD5:45 pmChicago O'Hare Intl
4h 25m
SAN8:10 pmSan Diego

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 $340. 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 $351.

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 $391. 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 $501.

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 evening. Flights from San Diego to Chicago during this time can be as low as $356. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $436.

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?

The best time to book a flight to Chicago from San Diego is 47 days out, which is when prices tend to be around $422. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $318.

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 54% 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 December 2024, prices for San Diego to Chicago flights are approximately 6% 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

$54

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 $54. The best round-trip flight deal from San Diego to Chicago found on momondo in the last 72 hours is $105.
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)

  • 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?

  • 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?

  • 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
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $91Free CancellationRating
6.1
3,468 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $97Free CancellationRating
6.3
8,107 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $217Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $244Free CancellationRating
7.4
9,009 reviews
Search United Airlines flights
DeltaPriceFrom $251Free CancellationRating
8.0
8,580 reviews
Search Delta flights
SouthwestPriceFrom $269Free CancellationRating
8.1
4,765 reviews
Search Southwest flights
Alaska AirlinesPriceFrom $391Free CancellationRating
8.0
9,554 reviews
Search Alaska Airlines flights
  • Southwest Flights From San Diego to Chicago

    Southwest flight deals from San Diego to Chicago start from $269 round-trip. Over the 14 Southwest flights for this route in a normal week, average airfare is usually $477 round-trip - but some users have found much cheaper deals with momondo.

  • Alaska Airlines Flights From San Diego to Chicago

    Alaska Airlines (8.0/10 from 9,555 reviews) operates around 18 flights from San Diego to Chicago in any given week. The average Alaska Airlines airfare for this route is around $757, with deals from around $391 rare but found on momondo. Referenced prices are for round-trip San Diego to Chicago flight searches in the last 72 hours.


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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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