Nonstop flights from San Diego to Chicago

4 airlines fly from San Diego (SAN) to 2 Chicago airports (ORD and MDW), with up to 17 flights a day.

SANORD

Routes

2 airport pairs

When they leave

San Diego time

6:15a10:45pFirst departure 6:15 AM, last 10:45 PM

11 in the morning, 6:15 AM to 11:10 AM, then four in the afternoon, 1:03 PM to 4:08 PM, then four in the evening, 5:45 PM to 10:45 PM.

Every flight

Earliest first

6:15 AM→12:50 PMSAN to ORDAmerican AirlinesBoeing 737 MAX 8Daily
6:18 AM→12:37 PMSAN to ORDUnited AirlinesAirbus A321neoDaily
6:20 AM→12:20 PMSAN to MDWSouthwest AirlinesBoeing 737 MAX 8Sun
6:45 AM→12:45 PMSAN to MDWSouthwest AirlinesBoeing 737 MAX 8Mon, Thu, Fri, Sun
6:55 AM→12:55 PMSAN to MDWSouthwest AirlinesBoeing 737 MAX 8Tue, Wed, Sat
7:03 AM→1:22 PMSAN to ORDAlaska AirlinesBoeing 737 MAX 9Daily
7:24 AM→1:54 PMSAN to ORDAmerican AirlinesBoeing 737Daily
9:48 AM→4:23 PMSAN to ORDAmerican AirlinesBoeing 737Daily
10:40 AM→4:59 PMSAN to ORDUnited AirlinesBoeing 737 MAX 9Daily
11:05 AM→5:00 PMSAN to MDWSouthwest AirlinesBoeing 737 MAX 8Mon, Thu, Fri
11:10 AM→5:05 PMSAN to MDWSouthwest AirlinesBoeing 737 MAX 8Tue, Wed, Sat
1:03 PM→7:21 PMSAN to ORDAlaska AirlinesBoeing 737-800Daily
1:11 PM→7:59 PMSAN to ORDAmerican AirlinesAirbus A321Mon, Tue, Wed, Fri, Sat
1:11 PM→7:59 PMSAN to ORDAmerican AirlinesAirbus A321Thu, Sun
2:15 PM→8:36 PMSAN to ORDUnited AirlinesAirbus A321neoDaily
4:08 PM→10:14 PMSAN to ORDUnited AirlinesBoeing 737Daily
5:45 PM→11:59 PMSAN to ORDAlaska AirlinesBoeing 737Mon, Thu, Fri, Sun
5:50 PM→11:45 PMSAN to MDWSouthwest AirlinesBoeing 737-700Mon, Thu, Fri
10:40 PM→4:43 AM⁺¹SAN to ORDUnited AirlinesBoeing 737 MAX 9Daily
10:40 PM→4:30 AM⁺¹SAN to MDWSouthwest AirlinesBoeing 737-700Daily
10:45 PM→5:02 AM⁺¹SAN to ORDAmerican AirlinesAirbus A321Daily

Schedules last checked Oct 7, 2026. Times are local.

Flying from San Diego to Chicago

American Airlines flies 5 times a day on the Airbus A321, Boeing 737 and Boeing 737 MAX 8. United Airlines flies 5 times a day on the Airbus A321neo, Boeing 737 MAX 9 and Boeing 737. Southwest Airlines flies 3 to 4 times a day on the Boeing 737 MAX 8 and Boeing 737-700. Alaska Airlines flies 2 to 3 times a day on the Boeing 737, Boeing 737 MAX 9 and Boeing 737-800.

Flights run every day of the week, from 15 on Tuesdays, Wednesdays and Saturdays to 17 on Mondays, Thursdays and Fridays. The first arrival in Chicago is at 12:20 PM and the last at 5:02 AM the next day.

SAN to ORD is the busiest airport pair, with 88 flights a week, then SAN to MDW with 24.

Flying back, Chicago to San Diego has 112 nonstop flights a week.

Return flights

Chicago to San DiegoView

Find the cheapest day to fly from San Diego to Chicago.

Schedules as of Oct 9, 2026.