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There are 7 ways to get from San Diego to Chicago by plane, train, bus or car

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  •  5h 34m

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

$174 - $556

Cheapest option

Fly to Chicago O'Hare  •  5h 58m

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

$104 - $398

5 alternative options

Fly to Milwaukee, train  •  8h 9m

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

$202 - $628

Train  •  45h 30m

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

$300 - $915

Bus  •  2 days 5h

  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

Bus, train  •  2 days 13h

  1. Take the bus from San Diego to Yuma Tijuana-Ciudad Juárez 19:50 / ...
  2. Take the train from Yuma Amtrak to Chicago Union Station Texas Eagle

$345 - $963

Drive  •  32h 37m

  1. Drive from San Diego to Chicago 2106.4 miles

$200 - $300

Questions & Answers

The cheapest way to get from San Diego to Chicago is to fly which costs $100 - $400 and takes 5h 58m.

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The quickest way to get from San Diego to Chicago is to fly which costs $170 - $600 and takes 5h 34m.

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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 5h.

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No, there is no direct train from San Diego to Chicago station. However, there are services departing from San Diego Santa Fe Depot and arriving at Chicago Union Station via Fullerton Amtrak Station. The journey, including transfers, takes approximately 45h 30m.

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The distance between San Diego and Chicago is 1742 miles. The road distance is 2106.4 miles.

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The best way to get from San Diego to Chicago without a car is to train which takes 45h 30m and costs $300 - $950.

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It takes approximately 5h 34m to get from San Diego to Chicago, including transfers.

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San Diego to Chicago bus services, operated by Greyhound USA, depart from San Diego, Ca station.

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San Diego to Chicago train services, operated by Amtrak, depart from San Diego Santa Fe Depot station.

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The best way to get from San Diego to Chicago is to fly which takes 5h 34m and costs $170 - $600. Alternatively, you can train, which costs $300 - $950 and takes 45h 30m, you could also bus, which costs $200 - $550 and takes 2 days 5h.

Mode details

Map of how to get from San Diego to Chicago.
Launch map view
  • Distance: 1741.8 miles
  • Duration: 5h 34m

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 Amtrak Station in around 45h 30m.

Airlines
Southwest Airlines
Website
southwest.com
Flights from San Diego to Chicago Midway
Ave. Duration
3h 56m
When
Every day
Estimated price
$270 - $1,100
Flights from San Diego to Chicago Midway via Phoenix
Ave. Duration
5h 35m
When
Every day
Estimated price
$270 - $1,100
Flights from San Diego to Chicago Midway via Denver
Ave. Duration
5h 40m
When
Saturday and Sunday
Estimated price
$270 - $1,100
Flights from San Diego to Chicago Midway via Las Vegas
Ave. Duration
5h 35m
When
Monday to Friday
Estimated price
$270 - $1,100
Flights from San Diego to Chicago Midway via St. Louis
Ave. Duration
5h 40m
When
Sunday
Estimated price
$270 - $1,100
Flights from San Diego to Milwaukee
Ave. Duration
3h 55m
When
Saturday
Estimated price
$390 - $1,200
Flights from San Diego to Milwaukee via Denver
Ave. Duration
5h 35m
When
Every day
Estimated price
$390 - $1,200
Flights from San Diego to Milwaukee via Phoenix
Ave. Duration
5h 37m
When
Every day
Estimated price
$390 - $1,200
Flights from San Diego to Milwaukee via St. Louis
Ave. Duration
5h 37m
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$390 - $1,200
Flights from San Diego to Milwaukee via Las Vegas
Ave. Duration
5h 46m
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$390 - $1,200
United Airlines
Website
united.com
Flights from San Diego to Chicago O'Hare
Ave. Duration
4h 1m
When
Every day
Estimated price
$220 - $1,000
Flights from San Diego to Chicago O'Hare via Denver
Ave. Duration
5h 57m
When
Every day
Estimated price
$220 - $1,000
Flights from San Diego to Milwaukee via Denver
Ave. Duration
5h 45m
When
Every day
Estimated price
$330 - $1,100
American Airlines
Website
aa.com
Flights from San Diego to Chicago O'Hare
Ave. Duration
4h 10m
When
Every day
Estimated price
$230 - $900
Flights from San Diego to Chicago O'Hare via Phoenix
Ave. Duration
5h 54m
When
Every day
Estimated price
$230 - $900
Flights from San Diego to Chicago O'Hare via Los Angeles
Ave. Duration
5h 58m
When
Every day
Estimated price
$230 - $900
Frontier Airlines
Website
flyfrontier.com
Flights from San Diego to Chicago O'Hare via Denver
Ave. Duration
6h 14m
When
Tuesday, Thursday and Sunday
Estimated price
$230 - $800
Flights from San Diego to Milwaukee
Ave. Duration
3h 55m
When
Tuesday, Thursday and Sunday
Estimated price
$300 - $700
Spirit Airlines
Website
spirit.com
Flights from San Diego to Chicago O'Hare
Ave. Duration
4h 8m
When
Monday, Thursday, Friday, Saturday and Sunday
Estimated price
$140 - $750
Delta
Website
delta.com
Flights from San Diego to Milwaukee via Salt Lake City
Ave. Duration
5h 53m
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$290 - $1,100
Train operators
Amtrak

Amtrak is a rail service that connects the US and three Canadian provinces. Covering 21,000 route miles (34,000km) Amtrak operates more than 300 trains daily. These medium and long distance intercity services operate at speeds of up to 240km/h, to more than 500 destinations. Founded in 1971, it is based in Washington, D.C. and offers four classes of travel: First Class, Sleeper, Business and Coach. Ticket fares are divided into five subclasses: Saver, Value, Flexible, Business and Premium. Amtrak trains are known for their wide seats, plug-in power, big windows and storage capabilities.

Rome2rio's guide to Amtrak
Contact Details
Phone
+1 215-856-7924
Website
amtrak.com
Train from Milwaukee Intermodal Station to Chicago Union Station
Ave. Duration
1h 29m
Frequency
Every 4 hours
Estimated price
$28 - $60
Website
amtrak.com
Coach Seat
$28 - $45
Flexi Coach Seat
$50 - $75
Business Coach Seat
$40 - $60
Room
$150 - $220
Train from San Diego Santa Fe Depot to Fullerton Amtrak Station
Ave. Duration
2h 15m
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 Amtrak Station to Chicago Union Station
Ave. Duration
42h 15m
Frequency
Once 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
Train from Yuma Amtrak to Chicago Union Station
Ave. Duration
2 days 9h
Frequency
3 times a week
Estimated price
$300 - $900
Website
amtrak.com
Coach Seat
$300 - $450
Flexi Coach Seat
$500 - $800
Business Coach Seat
$650 - $900
Room
$1,100 - $1,600
Bus operators
Greyhound USA

Greyhound is a leading bus company based in Dallas, Texas, serving over 3800 destinations across North America, Mexico and Canada. Greyhound carries around 18 million passengers a year who travel 5.4 billion miles (8.6 billion km) a year on their fleet of around 1700 vehicles. For travel flexibility, you can board or get off a Greyhound bus at official Greyhound stations, partner stations and curbside stops. There are around 230 Greyhound stations across the US where you can both catch your bus and buy tickets, that are also available on the official website and via the mobile app.

Rome2rio's guide to Greyhound USA
Contact Details
Phone
+1 214-849-8100/1-800-231-2222
Email
ifsr@greyhound.com
Website
greyhound.com
Bus from San Diego, Ca to San Bernardino, Ca
Ave. Duration
2h 30m
Frequency
Twice daily
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 2h
Frequency
3 times a day
Estimated price
$190 - $500
Website
greyhound.com
Economy
$190 - $320
Flexible
$380 - $500
Greyhound Mexico
Phone
01-800 890 6821
Website
greyhound.com.mx
Bus from San Diego to Yuma
Ave. Duration
3h 40m
Frequency
Every 4 hours
Estimated price
$45 - $65
Schedules at
greyhound.com.mx

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.

More Questions & Answers

The quickest flight from San Diego Airport to Chicago Midway Airport is the direct flight which takes 3h 50m.

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San Diego to Chicago bus services, operated by Greyhound USA, arrive at Chicago, Il station.

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Chicago is 2h ahead of San Diego. It is currently 2:33 AM in San Diego and 4:33 AM in Chicago.

San Diego to Chicago train services, operated by Amtrak, arrive at Chicago Union Station.

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Yes, the driving distance between San Diego to Chicago is 2106 miles. It takes approximately 32h 37m to drive from San Diego to Chicago.

Get driving directions

Southwest Airlines offers flights from San Diego Airport to Chicago Midway Airport.

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Book your San Diego to Chicago train tickets online with Rome2rio.

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Book your San Diego to Chicago bus tickets online with Greyhound and Greyhound.

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There are 763+ hotels available in Chicago. Prices start at $75 USD per night.

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The best way to get from San Diego to San Diego Airport is to line 992 bus which takes 9m and costs $2 - $3.

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