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Cheap flights from San Diego to Chicago from $53

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 2/24. 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.
1:47 pm - 11:44 pmSAN-ORD
7h 57m1 stop
6:20 am - 5:33 pmORD-SAN
13h 13m1 stop
$98Frontier
Find Deal
Thu, Feb 6 - Sat, Feb 8
1:47 pm - 11:49 pmSAN-ORD
8h 02m1 stop
6:36 pm - 6:58 pmORD-SAN
26h 22m1 stop
$104Frontier
Find Deal
Thu, Jan 9 - Thu, Jan 30
6:06 pm - 5:30 amSAN-ORD
9h 24m1 stop
10:47 pm - 8:58 amORD-SAN
12h 11m1 stop
$132Spirit Airlines
Find Deal
Wed, Dec 18 - Thu, Jan 9
4:26 pm - 5:42 amSAN-ORD
11h 16m1 stop
10:47 pm - 8:58 amORD-SAN
12h 11m1 stop
Tue, Dec 17 - Thu, Jan 9
12:44 pm - 5:30 amSAN-ORD
14h 46m1 stop
7:50 am - 12:16 amORD-SAN
18h 26m1 stop
Tue, Jan 7 - Mon, Jan 13
5:58 pm - 5:30 amSAN-ORD
9h 32m1 stop
9:53 pm - 9:15 amORD-SAN
13h 22m1 stop
$142Spirit Airlines
Find Deal
Fri, Dec 13 - Mon, Dec 16
6:25 am - 5:47 pmSAN-MDW
9h 22m1 stop
6:00 am - 1:16 pmMDW-SAN
9h 16m1 stop
$320Delta
Find Deal
Wed, Jan 8 - Sat, Jan 11
7:25 am - 4:12 pmSAN-MDW
6h 47m1 stop
10:57 am - 6:51 pmMDW-SAN
9h 54m1 stop
$373Delta
Find Deal
Sat, Jan 18 - Sat, Jan 25
4:50 pm - 10:40 pmSAN-MDW
3h 50mnonstop
6:10 am - 8:40 amMDW-SAN
4h 30mnonstop
$412Southwest
Find Deal
Wed, Dec 25 - Thu, Jan 2
4:50 pm - 10:40 pmSAN-MDW
3h 50mnonstop
3:40 pm - 8:15 pmMDW-SAN
6h 35m1 stop
$421Southwest
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Wed, Dec 25 - Thu, Jan 2
8:08 pm - 5:05 amSAN-ORD
6h 57m1 stop
$53Frontier
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Mon, Feb 24
4:06 pm - 12:17 amSAN-MDW
6h 11m1 stop
$53Frontier
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Thu, Feb 27
1:47 pm - 11:49 pmSAN-ORD
8h 02m1 stop
$54Frontier
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Thu, Jan 9
6:06 pm - 5:30 amSAN-ORD
9h 24m1 stop
$61Spirit Airlines
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Wed, Dec 18
7:26 pm - 5:31 amSAN-ORD
8h 05m1 stop
$63Spirit Airlines
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Wed, Jan 29
10:39 pm - 4:42 amSAN-ORD
4h 03mnonstop
$176American Airlines
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Tue, Dec 24
4:50 pm - 10:40 pmSAN-MDW
3h 50mnonstop
$176Southwest
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Tue, Dec 24
7:10 am - 5:05 pmSAN-MDW
7h 55m2 stops
$186Southwest
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Tue, Jan 21
7:00 am - 1:11 pmSAN-ORD
4h 11mnonstop
$196United Airlines
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Wed, Jan 1
4:55 pm - 10:58 pmSAN-ORD
4h 03mnonstop
$221United Airlines
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Tue, Dec 24
2:52 pm - 11:18 pmSAN-ORD
6h 26m1 stop
1:39 pm - 10:18 pmORD-SAN
10h 39m1 stop
Mon, Dec 2 - Mon, Feb 3
2:52 pm - 11:18 pmSAN-ORD
6h 26m1 stop
8:46 pm - 7:45 amORD-SAN
12h 59m1 stop
$207Frontier
Find Deal
Mon, Dec 2 - Fri, Jan 31
10:27 pm - 4:35 amSAN-ORD
28h 08m1 stop
9:53 pm - 8:13 amORD-SAN
12h 20m1 stop
$371Spirit Airlines
Find Deal
Mon, Dec 2 - Fri, Dec 6
6:57 pm - 4:35 amSAN-ORD
7h 38m1 stop
9:53 pm - 8:13 amORD-SAN
12h 20m1 stop
$388Spirit Airlines
Find Deal
Mon, Dec 2 - Fri, Dec 6
12:50 pm - 3:30 pmSAN-ORD
24h 40m2 stops
6:15 pm - 1:27 amORD-SAN
9h 12m1 stop
$604United Airlines
Find Deal
Fri, Nov 29 - Sat, Nov 30
9:55 pm - 8:42 amSAN-ORD
8h 47m1 stop
10:05 am - 12:33 pmORD-SAN
4h 28mnonstop
$648American Airlines
Find Deal
Fri, Nov 29 - Sat, Nov 30
10:30 pm - 4:35 amSAN-ORD
4h 05mnonstop
7:10 am - 9:47 amORD-SAN
4h 37mnonstop
$750United Airlines
Find Deal
Fri, Nov 29 - Thu, Dec 19
10:39 pm - 4:43 amSAN-ORD
4h 04mnonstop
10:05 am - 12:33 pmORD-SAN
4h 28mnonstop
$837American Airlines
Find Deal
Mon, Dec 2 - Wed, Dec 4
1:10 pm - 7:10 pmSAN-MDW
4h 00mnonstop
8:05 am - 10:35 amMDW-SAN
4h 30mnonstop
$898Southwest
Find Deal
Sat, Nov 30 - Sat, Dec 7
8:15 am - 4:35 pmSAN-MDW
6h 20m1 stop
8:05 am - 10:35 amMDW-SAN
4h 30mnonstop
$903Southwest
Find Deal
Sat, Nov 30 - Sat, Dec 7
6:35 am - 12:51 pmSAN-ORD
4h 16mnonstop
9:07 pm - 11:40 pmORD-SAN
4h 33mnonstop
$351American Airlines
Find Deal
Wed, Dec 25 - Wed, Jan 1
6:40 am - 12:48 pmSAN-ORD
4h 08mnonstop
10:05 am - 12:36 pmORD-SAN
4h 31mnonstop
$352American Airlines
Find Deal
Sat, Jan 18 - Sat, Jan 25
10:39 pm - 4:42 amSAN-ORD
4h 03mnonstop
9:07 pm - 11:40 pmORD-SAN
4h 33mnonstop
$359American Airlines
Find Deal
Tue, Dec 24 - Tue, Dec 31
10:39 pm - 4:42 amSAN-ORD
4h 03mnonstop
9:07 pm - 11:40 pmORD-SAN
4h 33mnonstop
$401American Airlines
Find Deal
Tue, Dec 24 - Tue, Dec 31
4:50 pm - 10:40 pmSAN-MDW
3h 50mnonstop
5:35 am - 8:05 amMDW-SAN
4h 30mnonstop
$412Southwest
Find Deal
Wed, Dec 25 - Fri, Jan 3
10:30 pm - 4:35 amSAN-ORD
4h 05mnonstop
2:09 pm - 4:42 pmORD-SAN
4h 33mnonstop
$431United Airlines
Find Deal
Sat, Dec 28 - Tue, Dec 31
10:30 pm - 4:35 amSAN-ORD
4h 05mnonstop
2:00 pm - 4:33 pmORD-SAN
4h 33mnonstop
$442United Airlines
Find Deal
Mon, Dec 23 - Wed, Jan 1
6:55 pm - 12:50 amSAN-MDW
3h 55mnonstop
7:40 pm - 10:00 pmMDW-SAN
4h 20mnonstop
$467Southwest
Find Deal
Sun, Dec 22 - Wed, Jan 1
6:35 am - 12:51 pmSAN-ORD
4h 16mnonstop
5:30 pm - 7:51 pmORD-SAN
4h 21mnonstop
$653Alaska Airlines
Find Deal
Sun, Dec 22 - Fri, Jan 3
8:00 am - 2:14 pmSAN-ORD
4h 14mnonstop
10:05 am - 12:26 pmORD-SAN
4h 21mnonstop
$735Alaska Airlines
Find Deal
Mon, Dec 9 - Wed, Dec 11

Spirit Airlines flights from San Diego to Chicago

Our best Spirit Airlines deals on San Diego to Chicago flight tickets
Spirit Airlines
Dec 18
SAN6:06 pmSan Diego
9h 24m
1 stop
ORD5:30 amChicago O'Hare Intl
Jan 9
ORD10:47 pmChicago O'Hare Intl
12h 11m
1 stop
SAN8:58 amSan Diego
Spirit Airlines
Dec 13
SAN5:58 pmSan Diego
9h 32m
1 stop
ORD5:30 amChicago O'Hare Intl
Dec 16
ORD9:53 pmChicago O'Hare Intl
13h 22m
1 stop
SAN9:15 amSan Diego
Spirit Airlines
Jan 16
SAN5:01 pmSan Diego
10h 30m
1 stop
ORD5:31 amChicago O'Hare Intl
Jan 21
ORD1:39 pmChicago O'Hare Intl
12h 13m
1 stop
SAN11:52 pmSan Diego

Frontier flights from San Diego to Chicago

Our best Frontier deals on San Diego to Chicago flight tickets
Frontier
Feb 6
SAN1:47 pmSan Diego
7h 57m
1 stop
ORD11:44 pmChicago O'Hare Intl
Feb 8
ORD6:20 amChicago O'Hare Intl
13h 13m
1 stop
SAN5:33 pmSan Diego
Frontier
Jan 9
SAN1:47 pmSan Diego
8h 02m
1 stop
ORD11:49 pmChicago O'Hare Intl
Jan 30
ORD6:36 pmChicago O'Hare Intl
26h 22m
1 stop
SAN6:58 pmSan Diego
Frontier
Jan 15
SAN2:32 pmSan Diego
7h 41m
1 stop
MDW12:13 amChicago Midway
Jan 21
MDW8:15 amChicago Midway
7h 17m
1 stop
SAN1:32 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 $389. 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 $355. 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 54 days out, which is when prices tend to be around $394. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $246.

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 69% 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 November 2024, prices for San Diego to Chicago flights are approximately 14% 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

$53

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 $53. The best round-trip flight deal from San Diego to Chicago found on momondo in the last 72 hours is $98.
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
3,523 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $99Free CancellationRating
6.3
8,172 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $217Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $243Free CancellationRating
7.4
9,146 reviews
Search United Airlines flights
DeltaPriceFrom $251Free CancellationRating
8.0
8,730 reviews
Search Delta flights
SouthwestPriceFrom $252Free CancellationRating
8.1
4,979 reviews
Search Southwest flights
Alaska AirlinesPriceFrom $391Free CancellationRating
8.0
9,481 reviews
Search Alaska Airlines flights
  • Southwest Flights From San Diego to Chicago

    Southwest flight deals from San Diego to Chicago start from $252 round-trip. Over the 6 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 9,481 reviews) operates around 13 flights from San Diego to Chicago in any given week. The average Alaska Airlines airfare for this route is around $751, 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