Cheap Flights from San Diego, CA to Chicago, IL from $37

Return flight: Chicago – San Diego

On Cheapflightsplus.com you will find 13 direct and 281 connecting flights from San Diego to Chicago. You can compare airfare deals from 5 airlines and multiple travel sites from $37, book and save on cheap plane tickets and last minute offers. Also check out SAN-CHI flight schedule to find best flight time, convenient departure and arrival airports.

Find One-Way and Round-Trip San Diego to Chicago Flight Deals

To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights». To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight. Cheapest flights in November: $37 (one-way), $63 (round-trip).
Direct flights
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Full flight schedule will help you in detecting at what time planes fly from San Diego to Chicago. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.
Departure Arrival Flight Details Flight Duration Price
06:15 — 12:08
06:15 — 12:08 AS4323 Alaska Airlines
San Diego — Chicago
3h 53m
Find flight
from$373
07:00 — 13:09
07:00 — 13:09 UA797 United Airlines
San Diego — Chicago
4h 9m
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from$318
07:00 — 13:04
07:00 — 13:04 UA1502 United Airlines
San Diego — Chicago
4h 4m
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from$338
11:10 — 17:10
11:10 — 17:10 UA714 United Airlines
San Diego — Chicago
4h
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from$318
12:46 — 18:55
12:46 — 18:55 UA349 United Airlines
San Diego — Chicago
4h 9m
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from$345
13:34 — 19:39
13:34 — 19:39 AS4232 Alaska Airlines
San Diego — Chicago
4h 5m
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from$373
14:14 — 20:25
14:14 — 20:25 UA1998 United Airlines
San Diego — Chicago
4h 11m
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from$334
14:23 — 20:25
14:23 — 20:25 UA1023 United Airlines
San Diego — Chicago
4h 2m
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from$318
16:40 — 22:45
16:40 — 22:45 UA2486 United Airlines
San Diego — Chicago
4h 5m
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from$345
22:25 — 04:20
+1 day
22:25 — 04:20 UA2633 United Airlines
San Diego — Chicago
3h 55m
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from$338
22:30 — 04:35
+1 day
22:30 — 04:35 UA2352 United Airlines
San Diego — Chicago
4h 5m
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from$318
22:39 — 04:34
+1 day
22:39 — 04:34 AS6037 Alaska Airlines
San Diego — Chicago
3h 55m
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from$373
22:44 — 05:00
+1 day
22:44 — 05:00 AS6893 Alaska Airlines
San Diego — Chicago
4h 16m
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from$547
06:25 — 15:50
06:25 — 09:59 F92818 Frontier Airlines
San Diego — Denver
2h 29m stop
12:28 — 15:50 F91228 Frontier Airlines
Denver — Chicago
7h 25m
including layover
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from$59
06:25 — 17:30
06:25 — 09:59 F92818 Frontier Airlines
San Diego — Denver
3h 55m stop
13:54 — 17:30 F93426 Frontier Airlines
Denver — Chicago
9h 5m
including layover
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from$65
07:24 — 01:03
+1 day
06:25 — 09:56 F92818 Frontier Airlines
San Diego — Denver
10h 26m stop
20:59 — 00:35 F93172 Frontier Airlines
Denver — Chicago
15h 39m
including layover
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from$163
08:42 — 19:45
08:42 — 10:59 F91572 Frontier Airlines
San Diego — Phoenix
4h 18m stop
15:17 — 19:45 F91830 Frontier Airlines
Phoenix — Chicago
9h 3m
including layover
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from$83
08:42 — 20:14
08:56 — 11:22 F91572 Frontier Airlines
San Diego — Phoenix
4h 56m stop
17:38 — 21:58 F91736 Frontier Airlines
Phoenix — Chicago
9h 32m
including layover
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from$85
10:35 — 19:30
13:31 — 14:57 F91326 Frontier Airlines
San Diego — Las Vegas
1h 38m stop
18:18 — 23:59 F92146 Frontier Airlines
Las Vegas — Chicago
6h 55m
including layover
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from$103
10:53 — 22:15
12:12 — 15:44 F94928 Frontier Airlines
San Diego — Denver
4h 23m stop
12:28 — 15:50 F91228 Frontier Airlines
Denver — Chicago
9h 22m
including layover
Find flight
from$84
11:09 — 06:33
+1 day
10:35 — 12:01 F91326 Frontier Airlines
San Diego — Las Vegas
12h 20m stop
06:11 — 11:48 F92330 Frontier Airlines
Las Vegas — Chicago
17h 24m
including layover
Find flight
from$67
12:41 — 09:47
+1 day
12:41 — 16:13 F94990 Frontier Airlines
San Diego — Denver
13h 57m stop
06:10 — 09:47 F91484 Frontier Airlines
Denver — Chicago
19h 6m
including layover
Find flight
from$65
12:41 — 12:15
+1 day
12:41 — 16:13 F94990 Frontier Airlines
San Diego — Denver
16h 27m stop
08:40 — 12:15 F93174 Frontier Airlines
Denver — Chicago
21h 34m
including layover
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from$71
15:10 — 04:45
+1 day
15:10 — 16:30 NK3792 Spirit Airlines
San Diego — Las Vegas
6h 47m stop
23:17 — 04:45 NK182 Spirit Airlines
Las Vegas — Chicago
11h 35m
including layover
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from$37
15:38 — 00:13
+1 day
12:41 — 16:13 F94990 Frontier Airlines
San Diego — Denver
1h 51m stop
08:50 — 12:13 F92210 Frontier Airlines
Denver — Chicago
6h 35m
including layover
Find flight
from$65
16:24 — 06:10
+1 day
16:24 — 17:46 NK1767 Spirit Airlines
San Diego — Las Vegas
6h 44m stop
00:30 — 06:10 NK153 Spirit Airlines
Las Vegas — Chicago
11h 46m
including layover
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from$147
18:57 — 04:45
+1 day
18:57 — 20:16 NK2908 Spirit Airlines
San Diego — Las Vegas
3h 1m stop
23:17 — 04:45 NK182 Spirit Airlines
Las Vegas — Chicago
7h 48m
including layover
Find flight
from$76
18:57 — 11:52
+1 day
18:57 — 20:16 NK2908 Spirit Airlines
San Diego — Las Vegas
9h 59m stop
06:15 — 11:52 NK187 Spirit Airlines
Las Vegas — Chicago
14h 55m
including layover
Find flight
from$76
19:01 — 14:11
+1 day
19:01 — 22:34 F92712 Frontier Airlines
San Diego — Denver
12h 1m stop
10:35 — 14:11 F93172 Frontier Airlines
Denver — Chicago
17h 10m
including layover
Find flight
from$85
19:01 — 00:17
+2 days
19:01 — 22:34 F92712 Frontier Airlines
San Diego — Denver
22h 21m stop
20:55 — 00:17 F92210 Frontier Airlines
Denver — Chicago
27h 16m
including layover
Find flight
from$86
20:41 — 04:47
+1 day
20:41 — 22:15 F91470 Frontier Airlines
San Diego — Las Vegas
44m stop
22:59 — 04:47 F92146 Frontier Airlines
Las Vegas — Chicago
6h 6m
including layover
Find flight
from$79
20:41 — 06:33
+1 day
20:41 — 22:15 F91470 Frontier Airlines
San Diego — Las Vegas
2h 44m stop
00:59 — 06:33 F92330 Frontier Airlines
Las Vegas — Chicago
7h 52m
including layover
Find flight
from$79
21:25 — 06:10
+1 day
13:45 — 15:05 NK1480 Spirit Airlines
San Diego — Las Vegas
1h 47m stop
23:17 — 04:45 NK182 Spirit Airlines
Las Vegas — Chicago
6h 45m
including layover
Find flight
from$85
21:30 — 10:42
+1 day
21:30 — 00:04 F92888 Frontier Airlines
San Diego — Phoenix
6h 16m stop
06:20 — 10:42 F91736 Frontier Airlines
Phoenix — Chicago
11h 12m
including layover
Find flight
from$120
09:08 — 00:24
+1 day
09:08 — 10:30 NK376 Spirit Airlines
San Diego — Las Vegas
1h 34m stop
12:04 — 17:05 NK3727 Spirit Airlines
Las Vegas — Houston
4h 42m stop
21:47 — 00:24 NK962 Spirit Airlines
Houston — Chicago
13h 16m
including layover
Find flight
from$145
13:45 — 06:25
+1 day
13:45 — 15:05 NK1480 Spirit Airlines
San Diego — Las Vegas
3h 25m stop
18:30 — 19:48 NK465 Spirit Airlines
Las Vegas — Los Angeles
4h 35m stop
00:23 — 06:25 NK486 Spirit Airlines
Los Angeles — Chicago
14h 40m
including layover
Find flight
from$135
13:45 — 09:25
+1 day
13:45 — 15:05 NK1480 Spirit Airlines
San Diego — Las Vegas
6h 15m stop
21:20 — 04:55 NK954 Spirit Airlines
Las Vegas — Miami
2h 10m stop
07:15 — 09:35 NK2 Spirit Airlines
Miami — Chicago
17h 40m
including layover
Find flight
from$135
17:58 — 10:55
+1 day
17:58 — 19:18 NK1480 Spirit Airlines
San Diego — Las Vegas
4h 41m stop
23:59 — 05:05 SY778 Sun Country Airlines
Las Vegas — Minneapolis
4h 2m stop
09:47 — 11:35 SY259 Sun Country Airlines
Minneapolis — Chicago
14h 57m
including layover
Find flight
from$163
*Departure and arrival times - local. Updated on April 4, 2025

Flight Information

Below we will explain in detail what the flights cost on the destination from San Diego to Chicago depends on and how to choose the most interesting flight option for you.

Distance between San Diego and Chicago is 2788 miles. Time difference between the cities is 2h. Airplanes depart 06:15 to 22:44 from 11 San Diego airport and arrive 06:15 to 22:44 to 7 Chicago airports. Average flight time is 4h 5m.

  • The fastest flight 3h 53m
  • Average flight time 4h 5m
  • The earliest flight 06:15
  • The latest flight 22:44
  • Distance 1733 ml

The cheapest months to travel to Chicago are november (from 37 $), january (from 67 $), december (from 79 $).

The most expensive months are february (from 79 $), december (from 79 $), january (from 67 $).

What is the lowest airfare San Diego to Chicago?

The cheapest plane ticket found by our users is $37. This airfare is for economy class on one-way NK3792 flight by Spirit Airlines for November 20, 2024 which leaves San Diego in San Diego at 15:10 am and arrives at Chicago O'Hare International at 04:45.

Economy class
$37
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Business class
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First class
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Popular Airlines on the Route

The flight San Diego — Chicago is served by 5 regular airlines and 3 low-cost airlines. Most of the flights on this route are operated by United Airlines - 102 departures per week at the price of from $ 226 . And the most expensive tickets are offered by Alaska Airlines airline - from $ 547.

Direct flights

There are 13 nonstop flights on the route. The fastest direct flight is AS4323 by Alaska Airlines takes 3h 53m and the cheapest is NK3792 by Spirit Airlines for $318.

See more direct flights

Connecting Flights

There are 281 flights with layovers on the route. The fastest connecting flight is UA264 by United Airlines takes 5h 40m and the cheapest is NK3792 by Spirit Airlines for $37.

  • from $226
    Find
  • AS - Alaska Airlines
    from $187
    Find
  • F9 - Frontier Airlines
    from $59
    Find
  • SY - Sun Country Airlines
    from $128
    Find
  • NK - Spirit Airlines
    from $37
    Find
See more connecting flights

Airports

You can fly from San Diego to Chicago from 11 airports (San Diego, San Diego Regional, Gillespie Field, Golden Triangle Reg., El Cajon, Lowndes County, Miramar NAS, Montgomery Field, North Island NAS, Brown Field Municipal, AFB).

San Diego airports

  • San Diego-SAN
    from $37
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  • San Diego Regional-USA
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  • Gillespie Field-SEE
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  • Golden Triangle Reg.-GTR
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  • El Cajon-CJN
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  • Lowndes County-UBS
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  • Miramar NAS-NKX
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  • Montgomery Field-MYF
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  • North Island NAS-NZY
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  • Brown Field Municipal-SDM
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  • AFB-CBM
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Chicago airports

  • O'Hare International-ORD
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  • Midway-MDW
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  • Dupage County-DPA
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  • Chicago FSS-CHI
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  • Merrill C Meigs (closed)-CGX
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  • Pal-Waukee-PWK
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  • Chicago NAS-NOH
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How to book a plane ticket yourself?

How to book an air ticket yourself?
  • Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
  • Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
  • Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
  • Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
  • That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.

    To find a plane ticket, please select dates.

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