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Cheap flights from San Diego to Chicago from $43

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 8/6. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Cheap round-trip flights

Southwest Logo
8:00 am - 1:55 pmSAN-MDW
3h 55mnonstop
Southwest Logo
8:25 am - 10:40 amMDW-SAN
4h 15mnonstop
$104Southwest
Find Deal
Tue, Sep 9 - Sat, Sep 13
Spirit Airlines Logo
6:15 am - 2:13 pmSAN-ORD
5h 58m1 stop
Spirit Airlines Logo
7:08 am - 5:55 pmORD-SAN
12h 47m1 stop
$106Spirit Airlines
Find Deal
Sat, Aug 2 - Tue, Aug 5
Southwest Logo
6:30 pm - 12:30 amSAN-MDW
4h 00mnonstop
Southwest Logo
8:25 am - 10:40 amMDW-SAN
4h 15mnonstop
$109Southwest
Find Deal
Thu, Aug 21 - Sat, Aug 23
 Logo
3:57 pm - 6:03 amSAN-ORD
12h 06m1 stop
 Logo
1:39 pm - 3:59 pmORD-SAN
4h 20mnonstop
Wed, Aug 6 - Mon, Aug 11
Frontier Logo
3:40 pm - 10:03 pmSAN-ORD
4h 23mnonstop
Frontier Logo
7:00 am - 9:20 amORD-SAN
4h 20mnonstop
$121Frontier
Find Deal
Thu, Aug 28 - Mon, Sep 1
 Logo
6:15 am - 2:13 pmSAN-ORD
5h 58m1 stop
 Logo
1:39 pm - 3:59 pmORD-SAN
4h 20mnonstop
Tue, Aug 5 - Tue, Aug 12
Frontier Logo
4:44 pm - 11:07 pmSAN-ORD
4h 23mnonstop
Frontier Logo
1:39 pm - 3:59 pmORD-SAN
4h 20mnonstop
$132Frontier
Find Deal
Wed, Aug 13 - Sat, Aug 16
American Airlines Logo
10:45 pm - 4:56 amSAN-ORD
4h 11mnonstop
American Airlines Logo
9:00 pm - 11:23 pmORD-SAN
4h 23mnonstop
$143American Airlines
Find Deal
Mon, Aug 4 - Mon, Aug 11
United Airlines Logo
10:20 pm - 4:30 amSAN-ORD
4h 10mnonstop
United Airlines Logo
2:06 pm - 4:28 pmORD-SAN
4h 22mnonstop
$157United Airlines
Find Deal
Fri, Aug 8 - Fri, Aug 15
American Airlines Logo
9:45 am - 9:05 pmSAN-ORD
9h 20m1 stop
American Airlines Logo
10:03 am - 12:27 pmORD-SAN
4h 24mnonstop
$169American Airlines
Find Deal
Sat, Sep 6 - Sat, Sep 20

Southwest flights from San Diego to Chicago

Our best Southwest deals on San Diego to Chicago flight tickets
Southwest
Sep 9
SAN8:00 amSan Diego
3h 55m
MDW1:55 pmChicago Midway
Sep 13
MDW8:25 amChicago Midway
4h 15m
SAN10:40 amSan Diego
Southwest
Aug 21
SAN6:30 pmSan Diego
4h 00m
MDW12:30 amChicago Midway
Aug 23
MDW8:25 amChicago Midway
4h 15m
SAN10:40 amSan Diego
Southwest
Sep 9
SAN8:30 amSan Diego
6h 20m
1 stop
MDW4:50 pmChicago Midway
Sep 13
MDW7:25 pmChicago Midway
4h 10m
SAN9:35 pmSan Diego

Spirit Airlines flights from San Diego to Chicago

Our best Spirit Airlines deals on San Diego to Chicago flight tickets
Spirit Airlines
Aug 2
SAN6:15 amSan Diego
5h 58m
1 stop
ORD2:13 pmChicago O'Hare Intl
Aug 5
ORD7:08 amChicago O'Hare Intl
12h 47m
1 stop
SAN5:55 pmSan Diego
Spirit Airlines
Aug 5
SAN6:15 amSan Diego
5h 58m
1 stop
ORD2:13 pmChicago O'Hare Intl
Aug 8
ORD7:08 amChicago O'Hare Intl
12h 47m
1 stop
SAN5:55 pmSan Diego
Spirit Airlines
Aug 5
SAN6:15 amSan Diego
5h 58m
1 stop
ORD2:13 pmChicago O'Hare Intl
Aug 12
ORD7:08 amChicago O'Hare Intl
12h 47m
1 stop
SAN5:55 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 August is, on average, the cheapest month to fly to Chicago from San Diego, with most prices found around $307. If you’re not able to fly to Chicago in August, then June is your next best option. Flight prices from San Diego to Chicago during June average around $314.

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 $441. 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 $593.

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 $324. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $520.

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 $397 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 $307 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 3% 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 July 2025, prices for San Diego to Chicago flights are approximately 24% 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

$43

Fastest flight time

3h 55m

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 $43. The best round-trip flight deal from San Diego to Chicago found on momondo in the last 72 hours is $104.
The fastest flight from San Diego to Chicago takes 3h 55m
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 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?

  • 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
Spirit AirlinesPriceFrom $92Free CancellationRating
6.3
8,060 reviews
Search Spirit Airlines flights
FrontierPriceFrom $116Free CancellationRating
5.9
3,268 reviews
Search Frontier flights
American AirlinesPriceFrom $210Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $245Free CancellationRating
7.4
8,843 reviews
Search United Airlines flights
DeltaPriceFrom $258Free CancellationRating
8.0
7,958 reviews
Search Delta flights
Alaska AirlinesPriceFrom $267Free CancellationRating
8.0
10,000 reviews
Search Alaska Airlines flights
SouthwestPriceFrom $275Free CancellationRating
8.0
4,253 reviews
Search Southwest flights
  • Alaska Airlines Flights From San Diego to Chicago

    Alaska Airlines flight deals from San Diego to Chicago start from $267 round-trip. Over the 35 Alaska Airlines flights for this route in a normal week, average airfare is usually $680 round-trip - but some users have found much cheaper deals with momondo.

  • Southwest Flights From San Diego to Chicago

    Southwest (8.0/10 from 4,252 reviews) operates around 18 flights from San Diego to Chicago in any given week. The average Southwest airfare for this route is around $446, with deals from around $275 rare but found on momondo. Referenced prices are for round-trip San Diego to Chicago flight searches in the last 72 hours.


Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Monticello
Chesterton
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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1 adult
Mon 7/14
Mon 7/21

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