Cheap Flights from San Diego, CA to Chicago, IL from $37
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
Best Flights from San Diego to Chicago Today
Price | Departure | Arrival | Flight Duration | Airline | Flight |
---|---|---|---|---|---|
from $318 | 11:10 San Diego San Diego | 17:10 Chicago O'Hare International | 4h 0m | United Airlines | UA714 |
from $373 | 06:15 San Diego San Diego | 12:08 Chicago O'Hare International | 3h 53m | Alaska Airlines | AS4323 |
from $547 | 22:44 San Diego San Diego | 05:00+1 день Chicago O'Hare International | 4h 16m | Alaska Airlines | AS6893 |
from $37 | 15:10 San Diego San Diego | 04:45+1 день Chicago O'Hare International | 11h 35m layover 6h 47m - Las Vegas | Spirit Airlines | NK3792 NK182 |
from $59 | 06:25 San Diego San Diego | 15:50 Chicago Midway | 7h 25m layover 2h 29m - Denver | Frontier Airlines | F92818 F91228 |
from $67 | 11:09 San Diego San Diego | 06:33+1 день Chicago Midway | 17h 24m layover 12h 20m - Las Vegas | Frontier Airlines | F91326 F92330 |
from $71 | 12:41 San Diego San Diego | 12:15+1 день Chicago O'Hare International | 21h 34m layover 16h 27m - Denver | Frontier Airlines | F94990 F93174 |
from $76 | 18:57 San Diego San Diego | 04:45+1 день Chicago O'Hare International | 7h 48m layover 3h 1m - Las Vegas | Spirit Airlines | NK2908 NK182 |
from $76 | 18:57 San Diego San Diego | 11:52+1 день Chicago O'Hare International | 14h 55m layover 9h 59m - Las Vegas | Spirit Airlines | NK2908 NK187 |
from $78 | 12:12 San Diego San Diego | 23:16 Chicago O'Hare International | 9h 4m layover 3h 58m - Denver | Frontier Airlines | F94928 F93174 |
from $79 | 20:41 San Diego San Diego | 04:47+1 день Chicago O'Hare International | 6h 6m layover 0h 44m - Las Vegas | Frontier Airlines | F91470 F92146 |
from $79 | 20:41 San Diego San Diego | 06:33+1 день Chicago Midway | 7h 52m layover 2h 44m - Las Vegas | Frontier Airlines | F91470 F92330 |
from $83 | 08:42 San Diego San Diego | 19:45 Chicago O'Hare International | 9h 3m layover 4h 18m - Phoenix | Frontier Airlines | F91572 F91830 |
from $84 | 10:53 San Diego San Diego | 22:15 Chicago Midway | 9h 22m layover 4h 23m - Denver | Frontier Airlines | F94928 F91228 |
from $84 | 12:12 San Diego San Diego | 17:30+1 день Chicago O'Hare International | 27h 18m layover 22h 10m - Denver | Frontier Airlines | F94928 F92048 |
from $85 | 21:25 San Diego San Diego | 06:10+1 день Chicago O'Hare International | 6h 45m layover 1h 47m - Las Vegas | Spirit Airlines | NK1480 NK182 |
Flight Schedule San Diego (California) to Chicago (Illinois)
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 |
Find flight
from$318 |
|
07:00 — 13:04
|
07:00 — 13:04
UA1502
United Airlines
San Diego — Chicago
|
4h 4m |
Find flight
from$338 |
|
11:10 — 17:10
|
11:10 — 17:10
UA714
United Airlines
San Diego — Chicago
|
4h |
Find flight
from$318 |
|
12:46 — 18:55
|
12:46 — 18:55
UA349
United Airlines
San Diego — Chicago
|
4h 9m |
Find flight
from$345 |
|
13:34 — 19:39
|
13:34 — 19:39
AS4232
Alaska Airlines
San Diego — Chicago
|
4h 5m |
Find flight
from$373 |
|
14:14 — 20:25
|
14:14 — 20:25
UA1998
United Airlines
San Diego — Chicago
|
4h 11m |
Find flight
from$334 |
|
14:23 — 20:25
|
14:23 — 20:25
UA1023
United Airlines
San Diego — Chicago
|
4h 2m |
Find flight
from$318 |
|
16:40 — 22:45
|
16:40 — 22:45
UA2486
United Airlines
San Diego — Chicago
|
4h 5m |
Find flight
from$345 |
|
22:25 — 04:20
+1 day
|
22:25 — 04:20
UA2633
United Airlines
San Diego — Chicago
|
3h 55m |
Find flight
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 |
Find flight
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 |
Find flight
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 |
Find flight
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 |
Find flight
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 |
Find flight
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 |
Find flight
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 |
Find flight
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 |
Find flight
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 |
Find flight
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 |
Find flight
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 |
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.
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.
- from $318Find
- AS - Alaska Airlinesfrom $373Find
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 $226Find
- AS - Alaska Airlinesfrom $187Find
- F9 - Frontier Airlinesfrom $59Find
- SY - Sun Country Airlinesfrom $128Find
- NK - Spirit Airlinesfrom $37Find
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-SANfrom $37Find
- San Diego Regional-USAFind
- Gillespie Field-SEEFind
- Golden Triangle Reg.-GTRFind
- El Cajon-CJNFind
- Lowndes County-UBSFind
- Miramar NAS-NKXFind
- Montgomery Field-MYFFind
- North Island NAS-NZYFind
- Brown Field Municipal-SDMFind
- AFB-CBMFind
Chicago airports
- O'Hare International-ORDFind
- Midway-MDWFind
- Dupage County-DPAFind
- Chicago FSS-CHIFind
- Merrill C Meigs (closed)-CGXFind
- Pal-Waukee-PWKFind
- Chicago NAS-NOHFind
Airplanes
There are flights to Chicago from San Diego by 5 airlines that use 1 aircraft brands. They range from huge modern airplanes to small-sized.
- Airbus A320from $382Find
Top Domestic Destinations from San Diego
You may also consider searching for discounted plane tickets to some other popular places from San Diego within United States.
- from $67Find
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- from $68Find
- from $54Find
- from $64Find
- from $71Find
- from $57Find
- from $76Find
- from $70Find
- from $76Find
Top International Destinations from San Diego
Our state-of-the art metasearch will definitely provide you with the best airfare on international flights. We’re proud to partner with many reliable travel suppliers located outside the US what gives us an opportunity to offer the most competitive prices on far destinations.
- from $65Find
- from $66Find
- from $79Find
- from $72Find
- from $72Find
- from $79Find
- from $68Find
- from $54Find
- from $65Find
- from $60Find
How to book a plane 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.