Directions from San Diego to Chicago

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2rio's travel planner.

Recommended option

Fly to Chicago Midway  •  5 h 38 min

  1. Fly from San Diego (SAN) to Chicago Midway (MDW) SAN - MDW

$174 - $556

Cheapest option

Fly to Chicago O'Hare  •  5 h 52 min

  1. Fly from San Diego (SAN) to Chicago O'Hare (ORD) SAN - ORD

$104 - $398

4 alternative options

Fly to Milwaukee, train  •  8 h 15 min

  1. Fly from San Diego (SAN) to Milwaukee (MKE) SAN - MKE
  2. Take the train from Milwaukee Intermodal Station Amtrak to Chicago Union Station Amtrak

$199 - $594

Train  •  45 h 44 min

  1. Take the train from San Diego Santa Fe Depot Amtrak to Fullerton Transportation Center Pacific Surfliner
  2. Take the train from Fullerton Transportation Center to Chicago Union Station Amtrak Southwest Chief

$300 - $915

Bus  •  2 days 5 h

  1. Take the bus from San Diego, Ca to San Bernardino, Ca 7000 / ...
  2. Take the bus from San Bernardino, Ca to Chicago, Il 1364

$207 - $538

Drive  •  32 h 37 min

  1. Drive from San Diego to Chicago 2106.4 miles

$200 - $300

What companies run services between San Diego, CA, USA and Chicago, IL, USA?

Southwest Airlines flies from San Diego to Chicago hourly. Alternatively, you can take a train from San Diego to Chicago via Fullerton Transportation Center in around 45 h 44 min.

Airlines
Southwest Airlines
Website
southwest.com
Flights from San Diego to Chicago Midway
Ave. Duration
3 h 51 min
When
Every day
Estimated price
$270 - $1,100
Flights from San Diego to Chicago Midway via Denver
Ave. Duration
5 h 30 min
When
Monday to Saturday
Estimated price
$270 - $1,100
Flights from San Diego to Chicago Midway via Phoenix
Ave. Duration
5 h 26 min
When
Every day
Estimated price
$270 - $1,100
Flights from San Diego to Chicago Midway via Las Vegas
Ave. Duration
5 h 31 min
When
Monday to Saturday
Estimated price
$270 - $1,100
Flights from San Diego to Chicago Midway via St. Louis
Ave. Duration
5 h 37 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$270 - $1,100
Flights from San Diego to Chicago Midway via Dallas
Ave. Duration
5 h 50 min
When
Saturday
Estimated price
$270 - $1,100
Flights from San Diego to Milwaukee
Ave. Duration
3 h 50 min
When
Monday to Friday
Estimated price
$390 - $1,200
Flights from San Diego to Milwaukee via Phoenix
Ave. Duration
5 h 45 min
When
Every day
Estimated price
$390 - $1,200
Flights from San Diego to Milwaukee via Denver
Ave. Duration
5 h 25 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$390 - $1,200
Flights from San Diego to Milwaukee via St. Louis
Ave. Duration
5 h 32 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$390 - $1,200
Flights from San Diego to Milwaukee via Las Vegas
Ave. Duration
5 h 45 min
When
Saturday
Estimated price
$390 - $1,200
American Airlines
Website
aa.com
Flights from San Diego to Chicago O'Hare
Ave. Duration
4 h 7 min
When
Every day
Estimated price
$230 - $900
Flights from San Diego to Chicago O'Hare via Phoenix
Ave. Duration
5 h 56 min
When
Every day
Estimated price
$230 - $900
Flights from San Diego to Milwaukee via Chicago O'Hare
Ave. Duration
6 h 4 min
When
Every day
Estimated price
$390 - $1,300
United Airlines
Website
united.com
Flights from San Diego to Chicago O'Hare
Ave. Duration
4 h 1 min
When
Every day
Estimated price
$220 - $1,000
Flights from San Diego to Chicago O'Hare via Denver
Ave. Duration
5 h 53 min
When
Every day
Estimated price
$220 - $1,000
Flights from San Diego to Milwaukee via Denver
Ave. Duration
5 h 44 min
When
Every day
Estimated price
$330 - $1,100
Delta
Website
delta.com
Flights from San Diego to Chicago O'Hare via Salt Lake City
Ave. Duration
5 h 58 min
When
Every day
Estimated price
$240 - $1,100
Flights from San Diego to Milwaukee via Minneapolis
Ave. Duration
5 h 47 min
When
Monday to Friday
Estimated price
$290 - $1,100
Flights from San Diego to Milwaukee via Salt Lake City
Ave. Duration
6 h 5 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$290 - $1,100
Spirit Airlines
Website
spirit.com
Flights from San Diego to Chicago O'Hare
Ave. Duration
4 h 11 min
When
Every day
Estimated price
$140 - $750
Flights from San Diego to Chicago O'Hare via Las Vegas
Ave. Duration
5 h 58 min
When
Every day
Estimated price
$140 - $750
Train operators
Amtrak
Phone
+1 1-800-872-7245
Website
amtrak.com
Train from Milwaukee Intermodal Station Amtrak to Chicago Union Station Amtrak
Ave. Duration
1 h 29 min
Frequency
Every 4 hours
Estimated price
$25
Website
amtrak.com
Coach Seat
$25
Train from San Diego Santa Fe Depot Amtrak to Fullerton Transportation Center
Ave. Duration
2 h 14 min
Frequency
Every 2 hours
Estimated price
$30 - $65
Website
amtrak.com
Coach Seat
$30 - $45
Flexi Coach Seat
$50 - $80
Business Coach Seat
$45 - $65
Room
$160 - $220
Train from Fullerton Transportation Center to Chicago Union Station Amtrak
Ave. Duration
42 h 30 min
Frequency
Twice daily
Estimated price
$270 - $850
Website
amtrak.com
Coach Seat
$270 - $400
Flexi Coach Seat
$480 - $700
Business Coach Seat
$550 - $850
Room
$1,000 - $1,400
Bus operators
Greyhound USA
Phone
+1 214-849-8100
Email
ifsr@greyhound.com
Website
greyhound.com
Bus from San Diego, Ca to San Bernardino, Ca
Ave. Duration
2 h 30 min
Frequency
Hourly
Estimated price
$16 - $40
Website
greyhound.com
Economy
$16 - $25
Flexible
$30 - $40
Bus from San Bernardino, Ca to Chicago, Il
Ave. Duration
2 days 2 h
Frequency
Hourly
Estimated price
$190 - $500
Website
greyhound.com
Economy
$190 - $320
Flexible
$380 - $500

Want to know more about travelling around United States

Rome2rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Questions & Answers

The distance between San Diego and Chicago is 2787 km. The road distance is 3370 km.

The cheapest way to get from San Diego to Chicago is to fly which costs $100 - $400 and takes 5 h 52 min.

The quickest way to get from San Diego to Chicago is to fly which takes 5 h 38 min and costs $170 - $600.

No, there is no direct train from San Diego to Chicago. However, there are services departing from San Diego Santa Fe Depot Amtrak and arriving at Chicago Union Station Amtrak via Fullerton Transportation Center. The journey, including transfers, takes approximately 45 h 44 min.

No, there is no direct bus from San Diego to Chicago. However, there are services departing from San Diego, Ca and arriving at Chicago, Il via San Bernardino, Ca. The journey, including transfers, takes approximately 2 days 5 h.

It takes approximately 5 h 38 min to get from San Diego to Chicago, including transfers.