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Cheap Flights from San Diego to Chicago

  • San Diego Chicago

    Thu, Feb 6 - Sat, Feb 8

    From US$133.57
  • San Diego Chicago

    Thu, Feb 6 - Sat, Feb 8

    From US$141.16
  • San Diego Chicago

    Thu, Jan 9 - Sun, Jan 12

    From US$148.74
  • San Diego Chicago

    Sat, Feb 8 - Sun, Feb 9

    From US$239.22
  • San Diego Chicago

    Fri, Feb 7 - Sun, Feb 9

    From US$254.40
  • San Diego Chicago

    Thu, Feb 13 - Sun, Feb 16

    From US$232.78

Prices shown are for 1 adult ticket including taxes & fees.(As ticket fares can change frequently, these advertised prices are for reference only. The actual prices will be shown at time of booking.)

San Diego to Chicago Flight Information

Below are some common questions asked about this flight route:

Best time to book San Diego to Chicago flights

Generally the best time to book San Diego to Chicago flights is two months in advance. And the cheapest days to fly are Tuesdays, Wednesdays, and Saturdays. Sunday is the most expensive.

How many direct flights from San Diego to Chicago?

There are 70 direct flights from San Diego to Chicago.

What is the most popular airline for non-stop flights from San Diego to Chicago?

American Airlines provides 50 of the non-stop flights between San Diego and Chicago.

Airlines flying this route:
Airports in San Diego:
Airports in Chicago:
Average duration of direct flights: 4h6m

San Diego to Chicago Flight Schedule

Flight info. Departure
Arrival
Route Weekly Schedule
07:14 SAN 13:19 ORD
San Diego to Chicago SMTWTFS Search
22:30 SAN 04:12 ORD
San Diego to Chicago SMTWTFS Search
11:38 SAN 17:48 ORD
San Diego to Chicago ----T-- Search
IB4450
07:45 SAN 13:52 ORD
San Diego to Chicago SMTWTFS Search
SK8824
Sas
10:55 SAN 17:00 ORD
San Diego to Chicago SMTWTFS Search
22:40 SAN 04:50 ORD
San Diego to Chicago -MTWTFS Search
07:45 SAN 13:52 ORD
San Diego to Chicago SMTWTFS Search
SK8818
Sas
14:15 SAN 20:11 ORD
San Diego to Chicago SMTWTFS Search
11:00 SAN 17:14 ORD
San Diego to Chicago SMTWTFS Search
07:45 SAN 13:55 ORD
San Diego to Chicago SMTWTFS Search
11:38 SAN 17:48 ORD
San Diego to Chicago SMTWTFS Search
AC5106
08:20 SAN 14:24 ORD
San Diego to Chicago SMTWTFS Search
LH9147
07:00 SAN 13:05 ORD
San Diego to Chicago SMTWTFS Search
LX3263
10:55 SAN 17:00 ORD
San Diego to Chicago SMTWTFS Search
07:00 SAN 13:05 ORD
San Diego to Chicago SMTWTFS Search
AC5544
22:30 SAN 04:26 ORD
San Diego to Chicago SMTWTFS Search
07:45 SAN 13:52 ORD
San Diego to Chicago S-T-TFS Search
LH9149
14:15 SAN 20:11 ORD
San Diego to Chicago SMTWTFS Search
08:30 SAN 14:31 ORD
San Diego to Chicago SMTWTFS Search
14:15 SAN 20:11 ORD
San Diego to Chicago SMTWTF- Search

San Diego to O'Hare International Airport (ORD)

12:51, Feb 6 - 19:52, Feb 8
UA | United Airlines
10h 21m
SAN - ORD
Nonstop
US$132
Round-trip from
Search
09:30, Feb 6 - 13:28, Feb 8
AA | American Airlines
4h 9m
SAN - ORD
Nonstop
US$140
Round-trip from
Search
14:50, Jan 9 - 11:20, Jan 12
NK | Spirit Airlines
4h 2m
SAN - ORD
Nonstop
US$148
Round-trip from
Search
11:33, Mar 6 - 13:30, Mar 11
AS | Alaska Airlines
4h 15m
SAN - ORD
Nonstop
US$531
Round-trip from
Search
07:00, Dec 18 - 07:20, Dec 23
DL | Delta Air Lines
9h 21m
SAN - ORD
1 stop
US$311
Round-trip from
Search

San Diego to Midway International Airport (MDW)

22:25, Dec 23 - 20:20, Dec 30
DL | Delta Air Lines
8h 43m
SAN - MDW
1 stop
US$424
Round-trip from
Search
22:30, Feb 7 - 07:45, Feb 9
DL | Delta Air Lines
9h 29m
SAN - MDW
2 stop
US$239
Round-trip from
Search

Prices shown are for 1 adult ticket including taxes & fees.(As ticket fares can change frequently, these advertised prices are for reference only. The actual prices will be shown at time of booking.)

Roundtrip vs One-Way Flights from San Diego to Chicago

There is usually no major price difference between buying a roundtrip flight versus a one-way flight. Increased flexibility is the main benefit when it comes to buying a one-way flight from San Diego to Chicago. However, booking a roundtrip flight is a simpler process. You can compare roundtrip and one-way flights by using our flight comparison tool.

Travel from San Diego to Chicago

Chicago attracts thousands of visitors every year for both business and pleasure. Planning a trip from San Diego to Chicago is easy when you use Trip.com to help you make travel arrangements. With Trip.com, you can search for available flights and hotel rooms, and then make your booking quickly and easily online.

A Trip to Remember

Make your journey from San Diego to Chicago a trip to remember when you use Trip.com to review city attractions before you arrive. With a preview of what's available at your destination, you can make any necessary reservations in advance for the best travel experience possible.