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Cheap flights from San Diego to Chicago

44 nonstop flights a week, 5 of them today. Operated by 4 airlines, about 4h 15m in the air, 1,731 mi (2,786 km). Tickets from $133, nonstop from $154.

Flights from San Diego to Chicago

Pick a departure date to see flights and seller prices

We search agencies and airlines for your day: nonstop and connecting flights, baggage, departure and arrival times.

Filters

Best fares from San Diego to Chicago

Lowest one-way prices found by recent searches for the next 120 days; press a card to search that date

Cheapest one-way $133 18 January 2027, with a connection Cheapest nonstop $154 12 November 2026, Southwest Airlines Cheapest in the next 7 days $136 14 November, Sat Cheapest weekend departure $136 Sat, 14 November 2026 Cheapest month January 2027 tickets from $133

San Diego to Chicago at a glance

flight time, from 3h 50m to 13h 26m
4h 15m
straight-line distance
1,731 mi (2,786 km)
flights a week
44
flights today
5
first and last departure
06:15 - 10:24
lowest price, with a connection, 18 January
$133
lowest nonstop price
$154
airlines
4

San Diego to Chicago ticket prices by month

Lowest one-way fare found by recent searches

Cheapest month: January 2027, tickets from $133. Prices come from searches over the last few days; check the search for your exact date.

The most expensive month is July 2027: from $195. The average across months is $154.

San Diego to Chicago flight schedule

44 flights a week, 5 today, 50 seasonal or one-off. Departure and arrival times are local.

FlightDepartsArrivesDurationDaysAircraft
WN 1746
Southwest Airlines
06:15 San Diego International, terminal 1
12:10 Chicago Midway International
3h 55m
Sat
Boeing 737
WN 674
Southwest Airlines
06:30 San Diego International, terminal 1
12:30 Chicago Midway International
4h
Mon, Tue, Wed, Thu
Boeing 737
WN 3754
Southwest Airlines
06:35 San Diego International, terminal 1
12:35 Chicago Midway International
4h
Mon, Thu, Fri, Sun
Boeing 737-800
AA 1861
American Airlines
06:42 San Diego International, terminal 2
12:47 , terminal 3
4h 5m
Mon, Thu, Fri, Sat, Sun
Airbus A321
UA 2343
United Airlines
06:50 San Diego International, terminal 2
13:09 , terminal 1
4h 19m
Daily
Airbus A320
AS 1446
Alaska Airlines
07:00 San Diego International, terminal 2
13:18 , terminal 2
4h 18m
Mon, Fri, Sat, Sun
Boeing 737-800
AS 1446
Alaska Airlines
07:02 San Diego International, terminal 2
13:17 , terminal 2
4h 15m
Daily
Boeing 737
AA 2273
American Airlines
07:41 San Diego International, terminal 2
14:00 , terminal 3
4h 19m
Daily
Boeing 737-800
WN 1865
Southwest Airlines
08:30 San Diego International, terminal 1
15:40 Chicago Midway International
5h 10m
Sat
WN 1064
Southwest Airlines
08:35 San Diego International, terminal 1
17:45 Chicago Midway International
7h 10m
Sat
AA 2343
American Airlines
10:11 San Diego International, terminal 2
16:29 , terminal 3
4h 18m
Fri, Sat
Airbus A321
AA 2343
American Airlines
10:12 San Diego International, terminal 2
16:30 , terminal 3
4h 18m
Mon, Tue, Wed, Thu, Sun
Boeing 737-800
AA 2343
American Airlines
10:24 San Diego International, terminal 2
16:43 , terminal 3
4h 19m
Mon, Thu, Fri, Sun
Boeing 737-800

Seasonal and one-off flights

Not operating in the next two weeks. The first of them is on 24 November.

FlightDepartsArrivesDurationDaysAircraft
WN 3048
Southwest Airlines
06:40 San Diego International, terminal 1
12:40 Chicago Midway International
4h
Seasonal
WN 3048
Southwest Airlines
06:55 San Diego International, terminal 1
12:50 Chicago Midway International
3h 55m
Seasonal
Boeing 737
AA 1861
American Airlines
06:41 San Diego International, terminal 2
12:46 , terminal 3
4h 5m
Seasonal
Airbus A321
AA 2343
American Airlines
10:14 San Diego International, terminal 2
16:29 , terminal 3
4h 15m
Seasonal
Boeing 737-800
AA 1861
American Airlines
07:44 San Diego International, terminal 2
14:00 , terminal 3
4h 16m
Seasonal
Boeing 737-800
WN 634
Southwest Airlines
08:15 San Diego International, terminal 1
14:15 Chicago Midway International
4h
Seasonal
Boeing 737
AS 1494
Alaska Airlines
10:29 San Diego International, terminal 2
16:47 , terminal 2
4h 18m
Seasonal
Boeing 737-900
UA 1579
United Airlines
06:45 San Diego International, terminal 2
22:11 , terminal 1
13h 26m
Seasonal
Airbus A320
AA 2081
American Airlines
07:21 San Diego International, terminal 2
13:37 , terminal 3
4h 16m
Seasonal
Boeing 737-800
AA 2081
American Airlines
06:15 San Diego International, terminal 2
12:30 , terminal 3
4h 15m
Seasonal
Boeing 737-800
WN 654
Southwest Airlines
06:40 San Diego International, terminal 1
12:35 Chicago Midway International
3h 55m
Seasonal
AA 2717
American Airlines
07:36 San Diego International, terminal 2
13:52 , terminal 3
4h 16m
Seasonal
Boeing 737-800
AA 2026
American Airlines
10:13 San Diego International, terminal 2
16:29 , terminal 3
4h 16m
Seasonal
Boeing 737-800
WN 3404
Southwest Airlines
07:40 San Diego International, terminal 1
13:30 Chicago Midway International
3h 50m
Seasonal
Boeing 737
WN 2687
Southwest Airlines
08:20 San Diego International, terminal 1
16:35 Chicago Midway International
6h 15m
Seasonal
AA 1494
American Airlines
06:11 San Diego International, terminal 2
12:30 , terminal 3
4h 19m
Seasonal
Airbus A321
UA 2343
United Airlines
07:00 San Diego International, terminal 2
12:55 , terminal 1
3h 55m
Seasonal
Airbus A320
WN 1772
Southwest Airlines
07:05 San Diego International, terminal 1
12:55 Chicago Midway International
3h 50m
Seasonal
Boeing 737
AS 1446
Alaska Airlines
08:00 San Diego International, terminal 2
13:54 , terminal 2
3h 54m
Seasonal
Boeing 737-900
AA 2131
American Airlines
10:15 San Diego International, terminal 2
16:29 , terminal 3
4h 14m
Seasonal
Boeing 737-800
UA 1710
United Airlines
10:30 San Diego International, terminal 2
16:39 , terminal 1
4h 9m
Seasonal
Boeing 737
WN 1772
Southwest Airlines
06:35 San Diego International, terminal 1
12:30 Chicago Midway International
3h 55m
Seasonal
Boeing 737-800
AA 562
American Airlines
10:15 San Diego International, terminal 2
16:29 , terminal 3
4h 14m
Seasonal
Boeing 737-800
WN 2553
Southwest Airlines
06:45 San Diego International, terminal 1
12:50 Chicago Midway International
4h 5m
Seasonal
WN 2901
Southwest Airlines
07:55 San Diego International, terminal 1
17:15 Chicago Midway International
7h 20m
Seasonal
Boeing 737-800
WN 2960
Southwest Airlines
06:15 San Diego International, terminal 1
12:30 Chicago Midway International
4h 15m
Seasonal
WN 2553
Southwest Airlines
07:00 San Diego International, terminal 1
13:05 Chicago Midway International
4h 5m
Seasonal
Boeing 737-800
WN 3718
Southwest Airlines
08:55 San Diego International, terminal 1
18:10 Chicago Midway International
7h 15m
Seasonal
WN 2046
Southwest Airlines
06:15 San Diego International, terminal 1
12:30 Chicago Midway International
4h 15m
Seasonal
Boeing 737
AA 518
American Airlines
06:15 San Diego International, terminal 2
12:33 , terminal 3
4h 18m
Seasonal
Boeing 737
WN 1313
Southwest Airlines
06:15 San Diego International, terminal 1
12:30 Chicago Midway International
4h 15m
Seasonal
Boeing 737
WN 4285
Southwest Airlines
10:15 San Diego International, terminal 1
16:05 Chicago Midway International
3h 50m
Seasonal
Boeing 737
WN 4392
Southwest Airlines
06:50 San Diego International, terminal 1
12:50 Chicago Midway International
4h
Seasonal
Boeing 737-800
WN 4213
Southwest Airlines
06:15 San Diego International, terminal 1
12:30 Chicago Midway International
4h 15m
Seasonal
Boeing 737-800
WN 4762
Southwest Airlines
08:20 San Diego International, terminal 1
14:15 Chicago Midway International
3h 55m
Seasonal
Boeing 737
WN 2090
Southwest Airlines
06:30 San Diego International, terminal 1
12:30 Chicago Midway International
4h
Seasonal
Boeing 737-800
AA 1191
American Airlines
07:28 San Diego International, terminal 2
13:51 , terminal 3
4h 23m
Seasonal
Boeing 737-800
AA 2733
American Airlines
09:57 San Diego International, terminal 2
16:23 , terminal 3
4h 26m
Seasonal
Boeing 737-800
AA 1228
American Airlines
07:28 San Diego International, terminal 2
13:50 , terminal 3
4h 22m
Seasonal
Boeing 737-800
AA 2484
American Airlines
10:05 San Diego International, terminal 2
16:27 , terminal 3
4h 22m
Seasonal
Boeing 737-800
WN 4557
Southwest Airlines
06:15 San Diego International, terminal 1
12:40 Chicago Midway International
4h 25m
Seasonal
Boeing 737
WN 4557
Southwest Airlines
07:50 San Diego International, terminal 1
13:50 Chicago Midway International
4h
Seasonal
Boeing 737
WN 4557
Southwest Airlines
06:30 San Diego International, terminal 1
12:45 Chicago Midway International
4h 15m
Seasonal
WN 4544
Southwest Airlines
10:00 San Diego International, terminal 1
16:00 Chicago Midway International
4h
Seasonal
Boeing 737
WN 4557
Southwest Airlines
07:10 San Diego International, terminal 1
13:20 Chicago Midway International
4h 10m
Seasonal
Boeing 737
WN 4544
Southwest Airlines
10:25 San Diego International, terminal 1
16:25 Chicago Midway International
4h
Seasonal
Boeing 737
AA 1228
American Airlines
07:30 San Diego International, terminal 2
13:59 , terminal 3
4h 29m
Seasonal
Boeing 737-800
AA 2484
American Airlines
09:57 San Diego International, terminal 2
16:29 , terminal 3
4h 32m
Seasonal
Boeing 737-800
AA 1228
American Airlines
07:24 San Diego International, terminal 2
13:54 , terminal 3
4h 30m
Seasonal
Boeing 737-800
AA 2484
American Airlines
09:48 San Diego International, terminal 2
16:23 , terminal 3
4h 35m
Seasonal
Boeing 737-800

Days of the week are taken from the schedule for the next 14 days; schedules change by season. Chicago is 2 hours ahead of San Diego. The search shows seat availability and the price for your date.

Airlines flying San Diego to Chicago

Flights a week by schedule and the cheapest nonstop fare of each airline found by recent searches

American Airlines19 a week Southwest Airlines11 a week United Airlines7 a week Alaska Airlines7 a week

Airports

Where flights from San Diego to Chicago depart and land

Departure from San Diego

San Diego International SAN

44 flights a week, terminals 1, 2, 2 mi (4 km) from the city centre

About the airport

Arrival in Chicago

Chicago Midway International MDW

11 flights a week, 9 mi (14 km) from the city centre

About the airport

When to visit Chicago

Weather by month

Best time to visit: May, June, July, August, September and October, +18° to +27° by day. In November it is +10° by day and +2° at night, with 7 rainy days.

Jan
0° −7° 10 days
Feb
+2° −6° 7 days
Mar
+9° 0° 12 days
Apr
+14° +5° 13 days
May
+19° +10° 11 days
Jun
+27° +17° 9 days
Jul
+27° +19° 12 days
Aug
+27° +19° 10 days
Sep
+24° +16° 7 days
Oct
+18° +10° 11 days
Nov
+10° +2° 7 days
Dec
+4° −3° 10 days

Daytime and night temperatures in °C, rainy days. Months with the most comfortable weather are in green. Long-term averages.

Frequently asked questions

How long is the flight from San Diego to Chicago?
A nonstop flight takes 4 hours 15 minutes on average, from 3h 50m to 13h 26m depending on the flight.
How far is Chicago from San Diego?
1,731 mi (2,786 km) in a straight line between the cities.
Which airlines fly nonstop from San Diego to Chicago?
American Airlines (19 a week), Southwest Airlines (11 a week), United Airlines (7 a week) and Alaska Airlines (7 a week).
How many flights a day are there from San Diego to Chicago?
5 flights today and 44 a week, about 6.3 a day on average.
When are the first and last flights from San Diego to Chicago?
The first departure is at 06:15 (WN1746), the last at 10:24 (AA2343). Local time.
What is the cheapest month to fly from San Diego to Chicago?
January 2027: tickets from $133. The most expensive is July 2027, from $195.
What is the cheapest upcoming date to fly from San Diego to Chicago?
18 January 2027 (Monday): from $133 one way, with a connection, by recent searches. The search shows the price for your dates.
Which airline is the cheapest from San Diego to Chicago?
Southwest Airlines: nonstop tickets from $154 on 12 November by recent searches. Prices change daily, so compare the sellers in the search.
What is the time difference between San Diego and Chicago?
Chicago is 2 hours ahead of San Diego. Schedule times on this page are local to each airport.
Which San Diego airport do flights to Chicago leave from?
San Diego International (44 a week).