Cheap flights from San Diego to Chicago from $58

Round-trip
1 adult
Economy
From?
To?
Tue 6/28
Tue 7/5

Deals available from 900+ travel sites.

Flight information for San Diego to Chicago
(SAN to CHI)

Find info about flight duration, direct flights, and airports for your flight from San Diego to Chicago

Best Price Found

$58

Fastest flight time

4h 09m

Direct flights

Mon, Tue, Wed, Fri, Sat and Sun

Airports in Chicago

3 airports
The best one-way flight to Chicago from San Diego in the past 72 hours is $58. The best round-trip flight deal from San Diego to Chicago found on momondo in the last 72 hours is $125.
The fastest flight from San Diego to Chicago takes 4h 09m
Direct flights go from San Diego to Chicago on Monday, Tuesday, Wednesday, Friday, Saturday and Sunday. Airlines offering direct flights are: LOT, Air Canada and Aer Lingus.
There are 3 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Chicago Greater Rockford (RFD)

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 from San Diego to Chicago?

October

The cheapest time of year to fly to Chicago from San Diego is October. Most expensive is May

What is the cheapest day to depart San Diego for Chicago?

Friday

The cheapest day of the week is typically Friday. The most expensive is typically Sunday

When is the cheapest time to fly from San Diego to Chicago?

in the evening

San Diego to Chicago flights are approximately 32% more expensive at noon than in the evening

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

Juneyao Airlines

American Airlines, Delta, and Frontier are the most popular carriers operating from San Diego to Chicago

What is the cheapest San Diego to Chicago flight route?

San Diego - Chicago O'Hare Intl

Fly from San Diego to Chicago O'Hare Intl for the best San Diego - Chicago flight prices

How far in advance should you book San Diego to Chicago flights?

31 days before

The cheapest time to buy a flight from San Diego to Chicago is approximately 31 days to departure

When traveling from San Diego to Chicago, the most popular airport to fly into is Chicago O'Hare Intl Airport. The majority of travelers flying into Chicago O'Hare Intl Airport from San Diego are departing from San Diego Airport. You may be looking for an airport near San Diego Airport to depart from when traveling to Chicago and luckily, there are options! You can try Santa Ana J. Wayne/Orange Cnty Airport which is located in Santa Ana, Ontario Airport which is located in Ontario, or Long Beach Municipal Airport which is located in Long Beach. If you are looking for alternate airports to fly into when traveling from San Diego, you can try Chicago Midway Airport or Chicago Greater Rockford Airport which are located in Chicago and Chicago respectively. The least expensive flight option from San Diego to Chicago will typically be SAN — ORD during the month of June with an average price of $125 RT.

Santa Ana J. Wayne/Orange Cnty Airport (SNA) to Chicago O'Hare Intl Airport (ORD)$208
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Ontario Airport (ONT) to Chicago O'Hare Intl Airport (ORD)$273
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San Diego Airport (SAN) to Chicago O'Hare Intl Airport (ORD)$125
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San Diego Airport (SAN) to Chicago Midway Airport (MDW)$261
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Ontario Airport (ONT) to Chicago Midway Airport (MDW)$228
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Long Beach Municipal Airport (LGB) to Chicago O'Hare Intl Airport (ORD)$296
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Easily compare round-trip flights from San Diego to Chicago

Below you can see the best fares for your round-trip flight route over the next three months. All fares were found on momondo this week. Browse the quickest and cheapest flights from San Diego to Chicago by changing tabs
Spirit Airlines
Oct 13
SAN5:26 amSan Diego
3h 58m
ORD9:24 amChicago O'Hare Intl
Oct 14
ORD2:15 amChicago O'Hare Intl
4h 21m
SAN6:36 amSan Diego
Multiple Airlines
Oct 8
SAN6:29 pmSan Diego
3h 55m
ORD10:24 pmChicago O'Hare Intl
Oct 14
ORD2:15 amChicago O'Hare Intl
4h 21m
SAN6:36 amSan Diego
Frontier
Jul 20
SAN12:26 pmSan Diego
11h 36m
1 stop
MDW12:02 amChicago Midway
Jul 30
MDW7:00 amChicago Midway
6h 41m
1 stop
SAN1:41 pmSan Diego
Spirit Airlines
Oct 13
SAN5:26 amSan Diego
3h 58m
ORD9:24 amChicago O'Hare Intl
Oct 16
ORD2:15 amChicago O'Hare Intl
4h 21m
SAN6:36 amSan Diego
Spirit Airlines
Oct 14
SAN5:26 amSan Diego
3h 58m
ORD9:24 amChicago O'Hare Intl
Oct 17
ORD2:15 amChicago O'Hare Intl
4h 21m
SAN6:36 amSan Diego
Spirit Airlines
Oct 18
SAN5:26 amSan Diego
3h 58m
ORD9:24 amChicago O'Hare Intl
Oct 26
ORD2:15 amChicago O'Hare Intl
4h 21m
SAN6:36 amSan Diego

Find the cheapest one-way flights from San Diego to Chicago

If you're looking for one-way flights from San Diego to Chicago, view some of our deals below provided by Frontier, Spirit Airlines and United Airlines
Spirit Airlines
Oct 13
SAN5:26 amSan Diego
3h 58m
ORD9:24 amChicago O'Hare Intl
Frontier
Aug 30
SAN12:24 pmSan Diego
11h 38m
1 stop
MDW12:02 amChicago Midway
Multiple Airlines
Aug 17
SAN6:18 pmSan Diego
24h 02m
1 stop
ORD6:20 pmChicago O'Hare Intl

Search last-minute flights to Chicago from San Diego

Find and compare round-trip flight prices for your last-minute flight from San Diego to Chicago
Frontier
Jun 28
SAN2:25 amSan Diego
9h 29m
1 stop
MDW11:54 amChicago Midway
Jul 8
MDW6:55 amChicago Midway
6h 44m
1 stop
SAN1:39 pmSan Diego
Spirit Airlines
Jul 3
SAN5:25 amSan Diego
9h 13m
1 stop
ORD2:38 pmChicago O'Hare Intl
Jul 11
ORD5:29 pmChicago O'Hare Intl
14h 49m
1 stop
SAN8:18 amSan Diego
Multiple Airlines
Jul 2
SAN6:18 pmSan Diego
23h 40m
1 stop
ORD5:58 pmChicago O'Hare Intl
Jul 9
ORD5:29 pmChicago O'Hare Intl
12h 10m
1 stop
SAN5:39 amSan Diego
Frontier
Jun 28
SAN2:25 amSan Diego
9h 29m
1 stop
MDW11:54 amChicago Midway
Jul 7
MDW10:36 amChicago Midway
10h 51m
1 stop
SAN9:27 pmSan Diego
Spirit Airlines
Jul 3
SAN3:44 pmSan Diego
22h 54m
1 stop
ORD2:38 pmChicago O'Hare Intl
Jul 8
ORD5:29 pmChicago O'Hare Intl
12h 54m
1 stop
SAN6:23 amSan Diego
Frontier
Jul 3
SAN2:25 amSan Diego
9h 29m
1 stop
MDW11:54 amChicago Midway
Jul 11
MDW3:50 pmChicago Midway
13h 27m
1 stop
SAN5:17 amSan Diego

Best airlines flying from San Diego to Chicago

Compare and see reviews for airlines that fly from San Diego to Chicago with momondo
AirlineRatingFree CancellationPrice
Juneyao AirlinesPriceFrom $12Free CancellationRating
0.0
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Spirit AirlinesPriceFrom $30Free CancellationRating
6.2
6.4

Boarding

5.9

Comfort

7.0

Crew

4.8

Entertainment

5.1

Food

Reviews

For once, Spirit was only 30 minutes late which is a miracle for them.

1 / 10
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FrontierPriceFrom $85Free CancellationRating
6.2
6.4

Boarding

5.8

Comfort

7.0

Crew

4.7

Entertainment

5.0

Food

Reviews

Even though I paid for a seat I had to move twice to cheaper seats that were not what I paid for.

1 / 10
Search Frontier flights
American AirlinesPriceFrom $94Free CancellationRating
7.1
7.4

Boarding

7.1

Comfort

8.0

Crew

6.8

Entertainment

6.4

Food

Reviews

A lady who wouldn’t shut up next to me. And the baggage crew ( probably not American ) out my bag on with everyone else’s and it was to go to the security

1 / 10
Search American Airlines flights
United AirlinesPriceFrom $97Free CancellationRating
7.2
7.5

Boarding

7.1

Comfort

8.0

Crew

6.9

Entertainment

6.6

Food

Reviews

Fast boarding… did not like the temperature to cold .

1 / 10
Search United Airlines flights
Alaska AirlinesPriceFrom $191Free CancellationRating
8.0
8.2

Boarding

7.9

Comfort

8.5

Crew

7.2

Entertainment

7.2

Food

Reviews

Nothing

1 / 10
Search Alaska Airlines flights
DeltaPriceFrom $191Free CancellationRating
7.8
7.9

Boarding

8.0

Comfort

8.3

Crew

7.7

Entertainment

7.3

Food

Reviews

This is another disease as if you have the Internet, you are ordinary deceivers!

1 / 10
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  • Alaska Airlines Flights From San Diego to Chicago

    Alaska Airlines flight deals from San Diego to Chicago start from $191 round-trip. Over the 21 Alaska Airlines flights for this route in a normal week, average airfare is usually $496 round-trip - but some users have found much cheaper deals with momondo.

  • United Airlines Flights From San Diego to Chicago

    United Airlines (7.2/10 from 864 reviews) operates around 19 flights from San Diego to Chicago in any given week. The average United Airlines airfare for this route is around $411, with deals from around $97 rare but found on momondo. Referenced prices are for round-trip San Diego to Chicago flight searches in the last 72 hours.


Spirit Airlines flights from San Diego to Chicago

Our best Spirit Airlines deals on San Diego to Chicago flight tickets
Spirit Airlines
Oct 13
SAN5:26 amSan Diego
3h 58m
ORD9:24 amChicago O'Hare Intl
Oct 14
ORD2:15 amChicago O'Hare Intl
4h 21m
SAN6:36 amSan Diego
Spirit Airlines
Oct 13
SAN5:26 amSan Diego
3h 58m
ORD9:24 amChicago O'Hare Intl
Oct 16
ORD2:15 amChicago O'Hare Intl
4h 21m
SAN6:36 amSan Diego
Spirit Airlines
Oct 14
SAN5:26 amSan Diego
3h 58m
ORD9:24 amChicago O'Hare Intl
Oct 17
ORD2:15 amChicago O'Hare Intl
4h 21m
SAN6:36 amSan Diego

Frontier flights from San Diego to Chicago

Our best Frontier deals on San Diego to Chicago flight tickets
Frontier
Jul 20
SAN12:26 pmSan Diego
11h 36m
1 stop
MDW12:02 amChicago Midway
Jul 30
MDW7:00 amChicago Midway
6h 41m
1 stop
SAN1:41 pmSan Diego
Frontier
Jul 12
SAN3:29 pmSan Diego
8h 33m
1 stop
MDW12:02 amChicago Midway
Jul 23
MDW3:22 pmChicago Midway
13h 55m
1 stop
SAN5:17 amSan Diego
Frontier
Aug 18
SAN4:23 pmSan Diego
7h 39m
1 stop
MDW12:02 amChicago Midway
Aug 22
MDW6:55 amChicago Midway
6h 46m
1 stop
SAN1:41 pmSan Diego

  • Are airlines flying from San Diego to Chicago offering flexible cancellation due to COVID-19?

    Due to the global impact of COVID-19, some of our airline partners operating flights from San Diego to Chicago, such as United Airlines, American Airlines, and Spirit Airlines may have put in place flexible cancellation policies. Use our site to search for all of the airlines offering this flexibility to you.

  • 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.



Alternative routes for San Diego to Chicago

Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times
Los Angeles to Chicago Flights
Fastest flight time3h 44m
Cheapest price$194
San Francisco to Chicago Flights
Fastest flight time6h 43m
Cheapest price$261
Oakland, California to Chicago Flights
Fastest flight time4h 04m
Cheapest price$168
Santa Ana to Chicago Flights
Fastest flight time3h 55m
Cheapest price$208
Burbank to Chicago Flights
Fastest flight time6h 14m
Cheapest price$202
San Jose to Chicago Flights
Fastest flight time4h 14m
Cheapest price$231
Los Angeles to St. Louis Flights
Fastest flight time3h 26m
Cheapest price$203
Ontario to Chicago Flights
Fastest flight time3h 56m
Cheapest price$233
Sacramento to Chicago Flights
Fastest flight time3h 53m
Cheapest price$202
Long Beach to Chicago Flights
Fastest flight time5h 26m
Cheapest price$296
San Francisco to St. Louis Flights
Fastest flight time5h 26m
Cheapest price$194
Ontario to St. Louis Flights
Fastest flight time4h 57m
Cheapest price$258

Similar San Diego to Chicago flights

Flexible with your destination? Broaden your search and find flights similar to your San Diego to Chicago route

Why use momondo?

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.

All flight searches from San Diego to Chicago on momondo can be filtered to show those which offer flexible booking policies.

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.

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.


Here's why travelers choose to use momondo
Flexible Travel
momondo understands the need for flexibility and we have a filter specifically for flights with no change fees.
Expert Insights
Data driven insights designed to help you find a great flight deal. From the cheapest time to depart to how far in advance to book.
Price Alerts
Track the price of your preferred flight route and be notified when it changes.