Cheap Flights from San Diego to Chicago (SAN to ORD)

Discover more affordable routes and cheaper dates from San Diego to Chicago (SAN to ORD) within a date range.

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US$444

6:23pm - 7:11pm
Sun Jul 6th 2025

22h 48m
San Diego (SAN) → Chicago (ORD)

1 Stop

8:10pm - 5:19pm
Sun Jul 13th 2025

23h 9m
Chicago (ORD) → San Diego (SAN)

1 Stop

Sun Jul 6th 2025 Sun Country Airlines · SY 408 Depart at 6:23pm from San Diego (SAN) Fly for 3h 36m Arrive at 11:59pm in Minneapolis (MSP)

Layover in Minneapolis for 17h 31m

Mon Jul 7th 2025 Sun Country Airlines · SY 261 Depart at 5:30pm from Minneapolis (MSP) Fly for 1h 41m Arrive at 7:11pm in Chicago (ORD)

Stay in Chicago for 6 nights — find accommodations with Kayak and Booking

Sun Jul 13th 2025 Sun Country Airlines · SY 262 Depart at 8:10pm from Chicago (ORD) Fly for 1h 40m Arrive at 9:50pm in Minneapolis (MSP)

Layover in Minneapolis for 17h 46m

Mon Jul 14th 2025 Sun Country Airlines · SY 407 Depart at 3:36pm from Minneapolis (MSP) Fly for 3h 43m Arrive at 5:19pm in San Diego (SAN)

Book Flight
US$466

9:00am - 7:11pm
Sun Jul 6th 2025

8h 11m
San Diego (SAN) → Chicago (ORD)

1 Stop

8:10pm - 5:19pm
Sun Jul 13th 2025

23h 9m
Chicago (ORD) → San Diego (SAN)

1 Stop

Sun Jul 6th 2025 Sun Country Airlines · SY 406 Depart at 9:00am from San Diego (SAN) Fly for 3h 36m Arrive at 2:36pm in Minneapolis (MSP)

Layover in Minneapolis for 2h 54m

Sun Jul 6th 2025 Sun Country Airlines · SY 261 Depart at 5:30pm from Minneapolis (MSP) Fly for 1h 41m Arrive at 7:11pm in Chicago (ORD)

Stay in Chicago for 7 nights — find accommodations with Kayak and Booking

Sun Jul 13th 2025 Sun Country Airlines · SY 262 Depart at 8:10pm from Chicago (ORD) Fly for 1h 40m Arrive at 9:50pm in Minneapolis (MSP)

Layover in Minneapolis for 17h 46m

Mon Jul 14th 2025 Sun Country Airlines · SY 407 Depart at 3:36pm from Minneapolis (MSP) Fly for 3h 43m Arrive at 5:19pm in San Diego (SAN)

Book Flight
US$598

10:30pm - 4:40am
Sun Jul 6th 2025

4h 10m
San Diego (SAN) → Chicago (ORD)

Direct

9:00am - 11:28am
Sun Jul 13th 2025

4h 28m
Chicago (ORD) → San Diego (SAN)

Direct

Sun Jul 6th 2025 United Airlines · UA 2352 Depart at 10:30pm from San Diego (SAN) Fly for 4h 10m Arrive at 4:40am in Chicago (ORD)

Stay in Chicago for 6 nights — find accommodations with Kayak and Booking

Sun Jul 13th 2025 United Airlines · UA 660 Depart at 9:00am from Chicago (ORD) Fly for 4h 28m Arrive at 11:28am in San Diego (SAN)

Book Flight
US$598

5:20pm - 11:35pm
Sun Jul 6th 2025

4h 15m
San Diego (SAN) → Chicago (ORD)

Direct

9:00am - 11:28am
Sun Jul 13th 2025

4h 28m
Chicago (ORD) → San Diego (SAN)

Direct

Sun Jul 6th 2025 United Airlines · UA 2486 Depart at 5:20pm from San Diego (SAN) Fly for 4h 15m Arrive at 11:35pm in Chicago (ORD)

Stay in Chicago for 6 nights — find accommodations with Kayak and Booking

Sun Jul 13th 2025 United Airlines · UA 660 Depart at 9:00am from Chicago (ORD) Fly for 4h 28m Arrive at 11:28am in San Diego (SAN)

Book Flight
US$608

10:30pm - 4:40am
Sun Jul 6th 2025

4h 10m
San Diego (SAN) → Chicago (ORD)

Direct

7:40pm - 11:41pm
Sun Jul 13th 2025

6h 1m
Chicago (ORD) → San Diego (SAN)

1 Stop

Sun Jul 6th 2025 United Airlines · UA 2352 Depart at 10:30pm from San Diego (SAN) Fly for 4h 10m Arrive at 4:40am in Chicago (ORD)

Stay in Chicago for 6 nights — find accommodations with Kayak and Booking

Sun Jul 13th 2025 United Airlines · UA 2155 Depart at 7:40pm from Chicago (ORD) Fly for 4h 30m Arrive at 10:10pm in Los Angeles (LAX)

Layover in Los Angeles for 0h 30m

Sun Jul 13th 2025 United Airlines · UA 5612 Depart at 10:40pm from Los Angeles (LAX) Fly for 1h 1m Arrive at 11:41pm in San Diego (SAN)

Book Flight
US$608

5:20pm - 11:35pm
Sun Jul 6th 2025

4h 15m
San Diego (SAN) → Chicago (ORD)

Direct

7:40pm - 11:41pm
Sun Jul 13th 2025

6h 1m
Chicago (ORD) → San Diego (SAN)

1 Stop

Sun Jul 6th 2025 United Airlines · UA 2486 Depart at 5:20pm from San Diego (SAN) Fly for 4h 15m Arrive at 11:35pm in Chicago (ORD)

Stay in Chicago for 6 nights — find accommodations with Kayak and Booking

Sun Jul 13th 2025 United Airlines · UA 2155 Depart at 7:40pm from Chicago (ORD) Fly for 4h 30m Arrive at 10:10pm in Los Angeles (LAX)

Layover in Los Angeles for 0h 30m

Sun Jul 13th 2025 United Airlines · UA 5612 Depart at 10:40pm from Los Angeles (LAX) Fly for 1h 1m Arrive at 11:41pm in San Diego (SAN)

Book Flight
US$608

10:30pm - 4:40am
Sun Jul 6th 2025

4h 10m
San Diego (SAN) → Chicago (ORD)

Direct

5:00am - 9:11am
Sun Jul 13th 2025

6h 11m
Chicago (ORD) → San Diego (SAN)

1 Stop

Sun Jul 6th 2025 United Airlines · UA 2352 Depart at 10:30pm from San Diego (SAN) Fly for 4h 10m Arrive at 4:40am in Chicago (ORD)

Stay in Chicago for 6 nights — find accommodations with Kayak and Booking

Sun Jul 13th 2025 United Airlines · UA 2666 Depart at 5:00am from Chicago (ORD) Fly for 2h 43m Arrive at 6:43am in Denver (DEN)

Layover in Denver for 1h 4m

Sun Jul 13th 2025 United Airlines · UA 2309 Depart at 7:47am from Denver (DEN) Fly for 2h 24m Arrive at 9:11am in San Diego (SAN)

Book Flight
US$608

5:20pm - 11:35pm
Sun Jul 6th 2025

4h 15m
San Diego (SAN) → Chicago (ORD)

Direct

5:00am - 9:11am
Sun Jul 13th 2025

6h 11m
Chicago (ORD) → San Diego (SAN)

1 Stop

Sun Jul 6th 2025 United Airlines · UA 2486 Depart at 5:20pm from San Diego (SAN) Fly for 4h 15m Arrive at 11:35pm in Chicago (ORD)

Stay in Chicago for 6 nights — find accommodations with Kayak and Booking

Sun Jul 13th 2025 United Airlines · UA 2666 Depart at 5:00am from Chicago (ORD) Fly for 2h 43m Arrive at 6:43am in Denver (DEN)

Layover in Denver for 1h 4m

Sun Jul 13th 2025 United Airlines · UA 2309 Depart at 7:47am from Denver (DEN) Fly for 2h 24m Arrive at 9:11am in San Diego (SAN)

Book Flight
US$676

10:30pm - 4:40am
Sun Jul 6th 2025

4h 10m
San Diego (SAN) → Chicago (ORD)

Direct

7:19am - 9:42am
Sun Jul 13th 2025

4h 23m
Chicago (ORD) → San Diego (SAN)

Direct

Sun Jul 6th 2025 United Airlines · UA 2352 Depart at 10:30pm from San Diego (SAN) Fly for 4h 10m Arrive at 4:40am in Chicago (ORD)

Stay in Chicago for 6 nights — find accommodations with Kayak and Booking

Sun Jul 13th 2025 United Airlines · UA 542 Depart at 7:19am from Chicago (ORD) Fly for 4h 23m Arrive at 9:42am in San Diego (SAN)

Book Flight
US$676

10:30pm - 4:40am
Sun Jul 6th 2025

4h 10m
San Diego (SAN) → Chicago (ORD)

Direct

8:10pm - 10:34pm
Sun Jul 13th 2025

4h 24m
Chicago (ORD) → San Diego (SAN)

Direct

Sun Jul 6th 2025 United Airlines · UA 2352 Depart at 10:30pm from San Diego (SAN) Fly for 4h 10m Arrive at 4:40am in Chicago (ORD)

Stay in Chicago for 6 nights — find accommodations with Kayak and Booking

Sun Jul 13th 2025 United Airlines · UA 734 Depart at 8:10pm from Chicago (ORD) Fly for 4h 24m Arrive at 10:34pm in San Diego (SAN)

Book Flight
US$676

5:20pm - 11:35pm
Sun Jul 6th 2025

4h 15m
San Diego (SAN) → Chicago (ORD)

Direct

7:19am - 9:42am
Sun Jul 13th 2025

4h 23m
Chicago (ORD) → San Diego (SAN)

Direct

Sun Jul 6th 2025 United Airlines · UA 2486 Depart at 5:20pm from San Diego (SAN) Fly for 4h 15m Arrive at 11:35pm in Chicago (ORD)

Stay in Chicago for 6 nights — find accommodations with Kayak and Booking

Sun Jul 13th 2025 United Airlines · UA 542 Depart at 7:19am from Chicago (ORD) Fly for 4h 23m Arrive at 9:42am in San Diego (SAN)

Book Flight
US$676

5:20pm - 11:35pm
Sun Jul 6th 2025

4h 15m
San Diego (SAN) → Chicago (ORD)

Direct

8:10pm - 10:34pm
Sun Jul 13th 2025

4h 24m
Chicago (ORD) → San Diego (SAN)

Direct

Sun Jul 6th 2025 United Airlines · UA 2486 Depart at 5:20pm from San Diego (SAN) Fly for 4h 15m Arrive at 11:35pm in Chicago (ORD)

Stay in Chicago for 6 nights — find accommodations with Kayak and Booking

Sun Jul 13th 2025 United Airlines · UA 734 Depart at 8:10pm from Chicago (ORD) Fly for 4h 24m Arrive at 10:34pm in San Diego (SAN)

Book Flight
US$676

6:30am - 12:49pm
Sun Jul 6th 2025

4h 19m
San Diego (SAN) → Chicago (ORD)

Direct

9:00am - 11:28am
Sun Jul 13th 2025

4h 28m
Chicago (ORD) → San Diego (SAN)

Direct

Sun Jul 6th 2025 United Airlines · UA 2343 Depart at 6:30am from San Diego (SAN) Fly for 4h 19m Arrive at 12:49pm in Chicago (ORD)

Stay in Chicago for 6 nights — find accommodations with Kayak and Booking

Sun Jul 13th 2025 United Airlines · UA 660 Depart at 9:00am from Chicago (ORD) Fly for 4h 28m Arrive at 11:28am in San Diego (SAN)

Book Flight
US$686

6:30am - 12:49pm
Sun Jul 6th 2025

4h 19m
San Diego (SAN) → Chicago (ORD)

Direct

7:40pm - 11:41pm
Sun Jul 13th 2025

6h 1m
Chicago (ORD) → San Diego (SAN)

1 Stop

Sun Jul 6th 2025 United Airlines · UA 2343 Depart at 6:30am from San Diego (SAN) Fly for 4h 19m Arrive at 12:49pm in Chicago (ORD)

Stay in Chicago for 7 nights — find accommodations with Kayak and Booking

Sun Jul 13th 2025 United Airlines · UA 2155 Depart at 7:40pm from Chicago (ORD) Fly for 4h 30m Arrive at 10:10pm in Los Angeles (LAX)

Layover in Los Angeles for 0h 30m

Sun Jul 13th 2025 United Airlines · UA 5612 Depart at 10:40pm from Los Angeles (LAX) Fly for 1h 1m Arrive at 11:41pm in San Diego (SAN)

Book Flight
US$686

10:30pm - 4:40am
Sun Jul 6th 2025

4h 10m
San Diego (SAN) → Chicago (ORD)

Direct

6:00am - 10:13am
Sun Jul 13th 2025

6h 13m
Chicago (ORD) → San Diego (SAN)

1 Stop

Sun Jul 6th 2025 United Airlines · UA 2352 Depart at 10:30pm from San Diego (SAN) Fly for 4h 10m Arrive at 4:40am in Chicago (ORD)

Stay in Chicago for 6 nights — find accommodations with Kayak and Booking

Sun Jul 13th 2025 United Airlines · UA 1295 Depart at 6:00am from Chicago (ORD) Fly for 4h 29m Arrive at 8:29am in Los Angeles (LAX)

Layover in Los Angeles for 0h 40m

Sun Jul 13th 2025 United Airlines · UA 4643 Depart at 9:09am from Los Angeles (LAX) Fly for 1h 4m Arrive at 10:13am in San Diego (SAN)

Book Flight
US$686

5:20pm - 11:35pm
Sun Jul 6th 2025

4h 15m
San Diego (SAN) → Chicago (ORD)

Direct

6:00am - 10:13am
Sun Jul 13th 2025

6h 13m
Chicago (ORD) → San Diego (SAN)

1 Stop

Sun Jul 6th 2025 United Airlines · UA 2486 Depart at 5:20pm from San Diego (SAN) Fly for 4h 15m Arrive at 11:35pm in Chicago (ORD)

Stay in Chicago for 6 nights — find accommodations with Kayak and Booking

Sun Jul 13th 2025 United Airlines · UA 1295 Depart at 6:00am from Chicago (ORD) Fly for 4h 29m Arrive at 8:29am in Los Angeles (LAX)

Layover in Los Angeles for 0h 40m

Sun Jul 13th 2025 United Airlines · UA 4643 Depart at 9:09am from Los Angeles (LAX) Fly for 1h 4m Arrive at 10:13am in San Diego (SAN)

Book Flight
US$686

6:30am - 12:49pm
Sun Jul 6th 2025

4h 19m
San Diego (SAN) → Chicago (ORD)

Direct

5:00am - 9:11am
Sun Jul 13th 2025

6h 11m
Chicago (ORD) → San Diego (SAN)

1 Stop

Sun Jul 6th 2025 United Airlines · UA 2343 Depart at 6:30am from San Diego (SAN) Fly for 4h 19m Arrive at 12:49pm in Chicago (ORD)

Stay in Chicago for 6 nights — find accommodations with Kayak and Booking

Sun Jul 13th 2025 United Airlines · UA 2666 Depart at 5:00am from Chicago (ORD) Fly for 2h 43m Arrive at 6:43am in Denver (DEN)

Layover in Denver for 1h 4m

Sun Jul 13th 2025 United Airlines · UA 2309 Depart at 7:47am from Denver (DEN) Fly for 2h 24m Arrive at 9:11am in San Diego (SAN)

Book Flight
US$794

7:39am - 6:18pm
Sun Jul 6th 2025

8h 39m
San Diego (SAN) → Chicago (ORD)

1 Stop

6:00am - 12:49pm
Sun Jul 13th 2025

8h 49m
Chicago (ORD) → San Diego (SAN)

1 Stop

Sun Jul 6th 2025 Hawaiian Airlines · HA 6577 Depart at 7:39am from San Diego (SAN) Fly for 1h 41m Arrive at 9:20am in San Francisco (SFO)

Layover in San Francisco for 2h 35m

Sun Jul 6th 2025 Hawaiian Airlines · HA 7000 Depart at 11:55am from San Francisco (SFO) Fly for 4h 23m Arrive at 6:18pm in Chicago (ORD)

Stay in Chicago for 6 nights — find accommodations with Kayak and Booking

Sun Jul 13th 2025 Hawaiian Airlines · HA 6301 Depart at 6:00am from Chicago (ORD) Fly for 4h 37m Arrive at 8:37am in Seattle (SEA)

Layover in Seattle for 1h 21m

Sun Jul 13th 2025 Hawaiian Airlines · HA 6883 Depart at 9:58am from Seattle (SEA) Fly for 2h 51m Arrive at 12:49pm in San Diego (SAN)

Book Flight

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@sarahbb1

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@eyupitsjohn

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Roaming Sonaa

@roamingsonaa

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Read Sonaa's 7 Amazing Skyscanner Alternatives for Booking Travel

ANDY TRAVELS

@andy_travels

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Travel With Bender

@travelwitbender

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Read Josh's Ultimate Guide To Find Cheap One Way Flights

Wesley Mergard

@travel.with.wes

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Read Wesley's My Best Cheap Flight Hacks (Why Pay More?)

Cheap Flights from San Diego to Chicago (SAN to ORD)

Sarah Belizaire

John Ford

Roaming Sonaa

ANDY TRAVELS

Travel With Bender

Wesley Mergard

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