Cheap Flights from San Diego, CA to Chicago, IL from $287
On Cheapflightsplus.com you will find 22 direct and 979 connecting flights from San Diego to Chicago. You can compare airfare deals from 9 airlines and multiple travel sites from $287, 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 $567 | 06:30 San Diego San Diego | 12:44 Chicago O'Hare International | 4h 14m | United Airlines | UA2182 |
from $567 | 16:51 San Diego San Diego | 23:02 Chicago O'Hare International | 4h 11m | United Airlines | UA1822 |
from $567 | 22:29 San Diego San Diego | 04:31+1 день Chicago O'Hare International | 4h 2m | United Airlines | UA2478 |
from $594 | 10:40 San Diego San Diego | 21:25 Chicago O'Hare International | 8h 45m | United Airlines | UA2627 |
from $610 | 22:46 San Diego San Diego | 05:01+1 день Chicago O'Hare International | 4h 15m | American Airlines | AA1244 |
from $670 | 10:51 San Diego San Diego | 17:05 Chicago O'Hare International | 4h 14m | United Airlines | UA2419 |
from $837 | 15:25 San Diego San Diego | 21:25 Chicago Midway | 4h 0m | Southwest Airlines | WN4326 |
from $837 | 19:15 San Diego San Diego | 01:10+1 день Chicago Midway | 3h 55m | Southwest Airlines | WN3581 |
from $856 | 06:55 San Diego San Diego | 15:00 Chicago Midway | 6h 5m | Southwest Airlines | WN2925 |
from $874 | 11:15 San Diego San Diego | 20:15 Chicago Midway | 7h 0m | Southwest Airlines | WN658 |
from $287 | 19:05 San Diego San Diego | 12:02+1 день Chicago O'Hare International | 14h 57m layover 9h 50m - Las Vegas | Spirit Airlines | NK744 NK1800 |
from $319 | 11:53 San Diego San Diego | 23:39 Chicago Midway | 9h 46m layover 3h 10m - Atlanta | Frontier Airlines | F92828 F91354 |
from $319 | 21:11 San Diego San Diego | 09:27+1 день Chicago Midway | 10h 16m layover 2h 31m - Orlando | Frontier Airlines | F91194 F91022 |
Flight Schedule San Diego (California) to Chicago (Illinois)
Departure | Arrival | Flight Details | Flight Duration | Price |
---|---|---|---|---|
06:15 — 12:31
|
06:15 — 12:31
AA518
American Airlines
San Diego — Chicago
|
4h 16m |
Find flight
from$1343 |
|
06:15 — 12:31
|
06:15 — 12:31
AS6050
Alaska Airlines
San Diego — Chicago
|
4h 16m |
Find flight
from$1343 |
|
06:30 — 12:44
|
06:30 — 12:44
UA2182
United Airlines
San Diego — Chicago
|
4h 14m |
Find flight
from$567 |
|
06:35 — 12:40
|
06:35 — 12:40
WN3279
Southwest Airlines
San Diego — Chicago
|
4h 5m |
Find flight
from$1173 |
|
06:55 — 15:00
|
06:55 — 15:00
WN2925
Southwest Airlines
San Diego — Chicago
|
6h 5m |
Find flight
from$856 |
|
09:00 — 17:30
|
09:00 — 17:30
WN2564
Southwest Airlines
San Diego — Chicago
|
6h 30m |
Find flight
from$998 |
|
10:25 — 16:25
|
10:25 — 16:25
WN1544
Southwest Airlines
San Diego — Chicago
|
4h |
Find flight
from$2488 |
|
10:40 — 21:25
|
10:40 — 21:25
UA2627
United Airlines
San Diego — Chicago
|
8h 45m |
Find flight
from$594 |
|
10:45 — 16:40
|
10:45 — 16:40
WN967
Southwest Airlines
San Diego — Chicago
|
3h 55m |
Find flight
from$1109 |
|
10:51 — 17:05
|
10:51 — 17:05
UA2419
United Airlines
San Diego — Chicago
|
4h 14m |
Find flight
from$670 |
|
11:15 — 20:15
|
11:15 — 20:15
WN658
Southwest Airlines
San Diego — Chicago
|
7h |
Find flight
from$874 |
|
11:31 — 17:45
|
11:31 — 17:45
AS6057
Alaska Airlines
San Diego — Chicago
|
4h 14m |
Find flight
from$973 |
|
11:31 — 17:45
|
11:31 — 17:45
AA2343
American Airlines
San Diego — Chicago
|
4h 14m |
Find flight
from$1290 |
|
14:10 — 20:23
|
14:10 — 20:23
UA2370
United Airlines
San Diego — Chicago
|
4h 13m |
Find flight
from$1048 |
|
15:20 — 23:05
|
15:20 — 23:05
WN3208
Southwest Airlines
San Diego — Chicago
|
5h 45m |
Find flight
from$1509 |
|
15:25 — 21:25
|
15:25 — 21:25
WN4326
Southwest Airlines
San Diego — Chicago
|
4h |
Find flight
from$837 |
|
16:51 — 23:02
|
16:51 — 23:02
UA1822
United Airlines
San Diego — Chicago
|
4h 11m |
Find flight
from$567 |
|
19:15 — 01:10
+1 day
|
19:15 — 01:10
WN3581
Southwest Airlines
San Diego — Chicago
|
3h 55m |
Find flight
from$837 |
|
19:55 — 01:55
+1 day
|
19:55 — 01:55
WN270
Southwest Airlines
San Diego — Chicago
|
4h |
Find flight
from$1488 |
|
22:29 — 04:31
+1 day
|
22:29 — 04:31
UA2478
United Airlines
San Diego — Chicago
|
4h 2m |
Find flight
from$567 |
|
22:46 — 05:01
+1 day
|
22:46 — 05:01
AA1244
American Airlines
San Diego — Chicago
|
4h 15m |
Find flight
from$610 |
|
22:46 — 05:01
+1 day
|
22:46 — 05:01
AS4093
Alaska Airlines
San Diego — Chicago
|
4h 15m |
Find flight
from$973 |
|
06:50 — 22:44
|
06:50 — 08:07
NK260
Spirit Airlines
San Diego — Las Vegas
8h 53m stop
17:00 — 22:44
NK182
Spirit Airlines
Las Vegas — Chicago
|
13h 54m including layover |
Find flight
from$486 |
|
11:53 — 23:39
|
11:53 — 19:23
F92828
Frontier Airlines
San Diego — Atlanta
3h 10m stop
22:33 — 23:39
F91354
Frontier Airlines
Atlanta — Chicago
|
9h 46m including layover |
Find flight
from$319 |
|
11:53 — 06:51
+1 day
|
22:15 — 05:45
F92828
Frontier Airlines
San Diego — Atlanta
10h 17m stop
05:40 — 06:51
NK1306
Spirit Airlines
Atlanta — Chicago
|
16h 58m including layover |
Find flight
from$379 |
|
12:01 — 07:29
+1 day
|
22:15 — 05:45
F92828
Frontier Airlines
San Diego — Atlanta
10h 34m stop
06:20 — 07:44
F91574
Frontier Airlines
Atlanta — Chicago
|
17h 28m including layover |
Find flight
from$376 |
|
12:51 — 00:44
+1 day
|
12:51 — 16:28
F9552
Frontier Airlines
San Diego — Denver
4h 51m stop
21:19 — 00:44
F9878
Frontier Airlines
Denver — Chicago
|
9h 53m including layover |
Find flight
from$338 |
|
13:15 — 21:34
|
20:07 — 21:41
F92946
Frontier Airlines
San Diego — Phoenix
1h 23m stop
17:23 — 22:48
F91376
Frontier Airlines
Phoenix — Chicago
|
6h 19m including layover |
Find flight
from$357 |
|
14:47 — 12:02
+1 day
|
14:47 — 16:21
F92120
Frontier Airlines
San Diego — Las Vegas
13h 59m stop
06:20 — 12:02
NK1800
Spirit Airlines
Las Vegas — Chicago
|
19h 15m including layover |
Find flight
from$346 |
|
17:15 — 12:02
+1 day
|
17:01 — 18:25
NK788
Spirit Airlines
San Diego — Las Vegas
11h 41m stop
06:20 — 12:02
NK1800
Spirit Airlines
Las Vegas — Chicago
|
16h 47m including layover |
Find flight
from$351 |
|
17:15 — 22:44
+1 day
|
17:15 — 18:39
NK788
Spirit Airlines
San Diego — Las Vegas
22h 21m stop
17:00 — 22:44
NK182
Spirit Airlines
Las Vegas — Chicago
|
27h 29m including layover |
Find flight
from$372 |
|
19:05 — 12:02
+1 day
|
19:05 — 20:30
NK744
Spirit Airlines
San Diego — Las Vegas
9h 50m stop
06:20 — 12:02
NK1800
Spirit Airlines
Las Vegas — Chicago
|
14h 57m including layover |
Find flight
from$287 |
|
19:49 — 09:39
+1 day
|
20:02 — 23:43
F9554
Frontier Airlines
San Diego — Denver
6h 49m stop
21:19 — 00:44
F9876
Frontier Airlines
Denver — Chicago
|
11h 50m including layover |
Find flight
from$357 |
|
20:02 — 19:21
+1 day
|
20:02 — 23:43
F9554
Frontier Airlines
San Diego — Denver
16h 15m stop
15:58 — 19:21
F9934
Frontier Airlines
Denver — Chicago
|
21h 19m including layover |
Find flight
from$357 |
|
20:35 — 16:40
+2 days
|
20:35 — 21:58
NK2754
Spirit Airlines
San Diego — Las Vegas
37h 4m stop
11:02 — 16:40
F91202
Frontier Airlines
Las Vegas — Chicago
|
42h 5m including layover |
Find flight
from$456 |
|
21:11 — 09:27
+1 day
|
21:11 — 05:09
F91194
Frontier Airlines
San Diego — Orlando
2h 31m stop
07:40 — 09:27
F91022
Frontier Airlines
Orlando — Chicago
|
10h 16m including layover |
Find flight
from$319 |
|
21:11 — 14:48
+1 day
|
21:11 — 05:09
F91194
Frontier Airlines
San Diego — Orlando
7h 16m stop
12:25 — 14:48
F91544
Frontier Airlines
Orlando — Chicago
|
15h 37m including layover |
Find flight
from$358 |
|
22:00 — 11:27
+1 day
|
22:00 — 23:29
F92946
Frontier Airlines
San Diego — Phoenix
6h 31m stop
06:00 — 11:27
F91374
Frontier Airlines
Phoenix — Chicago
|
11h 27m including layover |
Find flight
from$357 |
|
06:25 — 22:03
|
06:25 — 10:00
F9550
Frontier Airlines
San Diego — Denver
1h 46m stop
11:46 — 12:47
F9777
Frontier Airlines
Denver — Las Vegas
3h 38m stop
16:25 — 22:03
F92114
Frontier Airlines
Las Vegas — Chicago
|
13h 38m including layover |
Find flight
from$466 |
|
14:59 — 00:13
+2 days
|
14:59 — 16:27
G41249
Allegiant Air
San Diego — Orlando
24h 35m stop
17:02 — 18:54
F91013
Frontier Airlines
Orlando — Atlanta
4h 15m stop
23:09 — 00:13
F91356
Frontier Airlines
Atlanta — Chicago
|
34h 14m including layover |
Find flight
from$374 |
|
22:00 — 20:18
+2 days
|
22:00 — 23:29
F92946
Frontier Airlines
San Diego — Phoenix
23h 33m stop
23:02 — 06:30
F91286
Frontier Airlines
Phoenix — Orlando
11h 23m stop
17:53 — 20:18
F91154
Frontier Airlines
Orlando — Chicago
|
44h 18m including layover |
Find flight
from$386 |
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 22:46 from 11 San Diego airport and arrive 06:15 to 22:46 to 7 Chicago airports. Average flight time is 4h 14m.
- The fastest flight 3h 55m
- Average flight time 4h 14m
- The earliest flight 06:15
- The latest flight 22:46
- Distance 1733 ml
The cheapest months to travel to Chicago are august (from 287 $).
What is the lowest airfare San Diego to Chicago?
The cheapest plane ticket found by our users is $287. This airfare is for economy class on one-way NK744 flight by Spirit Airlines for August 31, 2023 which leaves San Diego in San Diego at 19:05 am and arrives at Chicago O'Hare International at 12:02.
Popular Airlines on the Route
The flight San Diego — Chicago is served by 9 regular airlines and 5 low-cost airlines. Most of the flights on this route are operated by American Airlines - 119 departures per week at the price of from $ 557 . And the most expensive tickets are offered by Southwest Airlines airline - from $ 2488.
Direct flights
There are 22 nonstop flights on the route. The fastest direct flight is WN3581 by Southwest Airlines takes 3h 55m and the cheapest is NK744 by Spirit Airlines for $567.
- from $610Find
- from $973Find
- from $837Find
- from $567Find
Connecting Flights
There are 979 flights with layovers on the route. The fastest connecting flight is WN4045 by Southwest Airlines takes 5h 20m and the cheapest is NK744 by Spirit Airlines for $287.
- from $557Find
- from $572Find
- from $319Find
- from $1207Find
- from $873Find
- from $561Find
- from $564Find
- from $287Find
- G4 - Allegiant Airfrom $374Find
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 $287Find
- San Diego Regional-USAfrom $374Find
- 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 9 airlines that use 10 aircraft brands. They range from huge modern airplanes to small-sized.
- Airbus A321from $319Find
- Airbus A320from $357Find
- Boeing 737-100/200from $358Find
- Airbus A318/319/320/321from $537Find
- Boeing 737-900from $564Find
- Boeing 737from $564Find
- A220-300from $564Find
- Boeing 737 MAX 9from $567Find
- Boeing 737-800from $568Find
- Boeing 757-200from $568Find
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 $70Find
- from $78Find
- from $67Find
- from $63Find
- from $62Find
- from $68Find
- from $71Find
- from $68Find
- from $73Find
- 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 $66Find
- from $61Find
- from $57Find
- from $76Find
- from $75Find
- from $79Find
- from $60Find
- from $54Find
- from $65Find
- from $64Find
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.