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Cheap flights from San Diego to Chicago from $67

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 6/25. 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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Find the cheapest flights from San Diego to Chicago

Cheap round-trip flights

KAYAK's recommended round-trip deals from the most popular airlines that fly from San Diego to Chicago.
Frontier Logo
4:53 pm - 10:56 pmSAN-ORD
4h 03mnonstop
Frontier Logo
1:56 pm - 4:08 pmORD-SAN
4h 12mnonstop
$136Frontier
Find Deal
Tue, Jun 17 - Wed, Jun 25
Frontier Logo
4:53 pm - 10:56 pmSAN-ORD
4h 03mnonstop
Frontier Logo
1:56 pm - 4:08 pmORD-SAN
4h 12mnonstop
$137Frontier
Find Deal
Sat, Jul 5 - Wed, Jul 9
Spirit Airlines Logo
9:08 pm - 6:33 amSAN-ORD
7h 25m1 stop
Spirit Airlines Logo
9:02 pm - 7:13 amORD-SAN
12h 11m1 stop
$172Spirit Airlines
Find Deal
Sun, May 4 - Wed, May 7
Spirit Airlines Logo
8:48 pm - 5:25 amSAN-ORD
6h 37m1 stop
Spirit Airlines Logo
9:02 pm - 7:13 amORD-SAN
12h 11m1 stop
$175Spirit Airlines
Find Deal
Tue, May 13 - Wed, May 21
Southwest Logo
5:35 pm - 11:35 pmSAN-MDW
4h 00mnonstop
Southwest Logo
9:00 pm - 11:15 pmMDW-SAN
4h 15mnonstop
$237Southwest
Find Deal
Sat, Jun 7 - Sat, Jun 14
Southwest Logo
4:25 pm - 12:25 amSAN-MDW
6h 00m1 stop
Southwest Logo
8:05 am - 10:25 amMDW-SAN
4h 20mnonstop
$247Southwest
Find Deal
Thu, May 29 - Sat, May 31
Alaska Airlines Logo
7:00 am - 11:39 pmSAN-ORD
14h 39m1 stop
Alaska Airlines Logo
7:18 pm - 9:02 amORD-SAN
15h 44m1 stop
$276Alaska Airlines
Find Deal
Tue, Jul 1 - Fri, Jul 11
Alaska Airlines Logo
10:15 pm - 6:59 pmSAN-ORD
18h 44m1 stop
Alaska Airlines Logo
7:59 pm - 9:02 amORD-SAN
15h 03m1 stop
$282Alaska Airlines
Find Deal
Sat, May 31 - Sat, Jun 7
American Airlines Logo
9:25 am - 6:24 pmSAN-ORD
6h 59m1 stop
American Airlines Logo
7:10 am - 9:30 amORD-SAN
4h 20mnonstop
$294American Airlines
Find Deal
Sat, May 31 - Sat, Jun 7
American Airlines Logo
10:39 pm - 4:47 amSAN-ORD
4h 08mnonstop
American Airlines Logo
9:33 pm - 11:59 pmORD-SAN
4h 26mnonstop
$297American Airlines
Find Deal
Thu, May 22 - Sat, May 31

Frontier flights from San Diego to Chicago

Our best Frontier deals on San Diego to Chicago flight tickets
Frontier
Jun 17
SAN4:53 pmSan Diego
4h 03m
ORD10:56 pmChicago O'Hare Intl
Jun 25
ORD1:56 pmChicago O'Hare Intl
4h 12m
SAN4:08 pmSan Diego
Frontier
Jul 5
SAN4:53 pmSan Diego
4h 03m
ORD10:56 pmChicago O'Hare Intl
Jul 9
ORD1:56 pmChicago O'Hare Intl
4h 12m
SAN4:08 pmSan Diego
Frontier
Jun 18
SAN4:53 pmSan Diego
4h 03m
ORD10:56 pmChicago O'Hare Intl
Jun 24
ORD1:56 pmChicago O'Hare Intl
4h 12m
SAN4:08 pmSan Diego

Delta flights from San Diego to Chicago

Our best Delta deals on San Diego to Chicago flight tickets
Delta
Jun 7
SAN10:30 pmSan Diego
9h 11m
1 stop
MDW9:41 amChicago Midway
Jun 14
MDW1:09 pmChicago Midway
6h 56m
1 stop
SAN6:05 pmSan Diego
Delta
May 30
SAN6:20 amSan Diego
6h 08m
1 stop
ORD2:28 pmChicago O'Hare Intl
May 30
ORD7:15 pmChicago O'Hare Intl
6h 38m
1 stop
SAN11:53 pmSan Diego
Delta
Jun 5
SAN10:00 pmSan Diego
7h 49m
1 stop
ORD7:49 amChicago O'Hare Intl
Jun 7
ORD4:30 pmChicago O'Hare Intl
8h 00m
1 stop
SAN10:30 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 Thursday when prices can be found for as low as $477. 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 $649.

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 $454. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $550.

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 14 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $420 when searching 14 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 $339 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.

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

As of April 2025, prices for San Diego to Chicago flights are approximately 7% 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

$67

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 $67. The best round-trip flight deal from San Diego to Chicago found on momondo in the last 72 hours is $136.
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 $93Free CancellationRating
6.3
7,926 reviews
Search Spirit Airlines flights
FrontierPriceFrom $107Free CancellationRating
6.0
3,281 reviews
Search Frontier flights
American AirlinesPriceFrom $222Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $250Free CancellationRating
7.4
8,667 reviews
Search United Airlines flights
DeltaPriceFrom $258Free CancellationRating
8.0
7,917 reviews
Search Delta flights
SouthwestPriceFrom $339Free CancellationRating
8.0
4,280 reviews
Search Southwest flights
Alaska AirlinesPriceFrom $391Free CancellationRating
8.0
9,882 reviews
Search Alaska Airlines flights
  • Southwest Flights From San Diego to Chicago

    Southwest flight deals from San Diego to Chicago start from $339 round-trip. Over the 22 Southwest flights for this route in a normal week, average airfare is usually $471 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 9,882 reviews) operates around 24 flights from San Diego to Chicago in any given week. The average Alaska Airlines airfare for this route is around $809, 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.


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
Portage
Lansing
Saint Joseph
Schererville
Valparaiso
Munster
Crown Point
Monticello
Chesterton
Griffith
Porter
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
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Tue 4/22
Tue 4/29

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