There are 6 ways to get from San Diego to Chicago by plane, train (Amtrak), bus (Flixbus, Greyhound), car, or train
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Fly to Chicago Midway International Airport
best- Fly from San Diego International Airport (SAN) to Chicago Midway International Airport (MDW)plane SAN - MDW
4h 31m$101–439Fly to Chicago O'Hare International Airport
cheapest- Fly from San Diego International Airport (SAN) to Chicago O'Hare International Airport (ORD)plane SAN - ORD
4h 50m$80–348Train (Amtrak)
- Take the train from San Diego to Fullerton Amtrak Stationtrain Pacific Surfliner
- Take the train from Fullerton Amtrak Station to Chicago Union Stationtrain Southwest Chief
46h 6m$576–1,359Bus
- Take the bus from San Diego to Los Angeles Union Stationbus
- Take the bus from Los Angeles Union Station to St Louis Bus Stationbus
- Take the bus from St Louis Bus Station to Chicago Bus Stationbus
2d 2h$354–573Drive 2,073.9 mi
- Drive from San Diego to Chicagocar 2,073.9 mi
32h 39m$379–547Fly to General Mitchell International Airport, train
- Fly from San Diego International Airport (SAN) to General Mitchell International Airport (MKE)plane SAN - MKE
- Take the train from Milwaukee to Chicago Union Stationtrain
7h$167–694
San Diego to Chicago by train (Amtrak)
Comparing Your Travel Options
The cheapest way to get from San Diego to Chicago is to fly which costs $80 - $350 and takes 4h 50m.
The fastest way to get from San Diego to Chicago is to fly which takes 4h 31m and costs $100 - $440.
No, there is no direct bus from San Diego to Chicago station. However, there are services departing from San Diego and arriving at Chicago Bus Station via Los Angeles Union Station and St Louis Bus Station. The journey, including transfers, takes approximately 2 days 2h.
No, there is no direct train from San Diego to Chicago station. However, there are services departing from San Diego and arriving at Chicago Union Station via Fullerton Amtrak Station. The journey, including transfers, takes approximately 46h 6m.
The distance between San Diego and Chicago is 1747 miles. The road distance is 2086 miles.
The best way to get from San Diego to Chicago without a car is to train which takes 46h 6m and costs $550 - $1,400.
It takes approximately 4h 31m to get from San Diego to Chicago, including transfers.
San Diego to Chicago bus services, operated by Flixbus USA, depart from San Diego station.
San Diego to Chicago train services, operated by Amtrak, depart from San Diego station.
The best way to get from San Diego to Chicago is to fly which takes 4h 31m and costs $100 - $440. Alternatively, you can train, which costs $550 - $1,400 and takes 46h 6m, you could also bus, which costs $350 - $600 and takes 2 days 2h.
What companies run services between San Diego, CA, USA and Chicago, IL, USA?
Southwest Airlines flies from San Diego International Airport (SAN) to Chicago Midway International Airport (MDW) every 4 hours. Alternatively, you can take a train from San Diego to Chicago Union Station via Fullerton Amtrak Station in around 46h 6m.
- Website
- southwest.com
Flights from San Diego International Airport to Chicago Midway International Airport
- Ave. Duration
- 3h 56m
- When
- Every day
- Estimated price
- $95–440
Flights from San Diego International Airport to Chicago Midway International Airport via Denver
- Ave. Duration
- 6h
- When
- Every day
- Estimated price
- $95–440
Flights from San Diego International Airport to Chicago Midway International Airport via St. Louis
- Ave. Duration
- 6h 20m
- When
- Monday, Thursday, and Friday
- Estimated price
- $100–450
Flights from San Diego International Airport to General Mitchell International Airport
- Ave. Duration
- 3h 55m
- When
- Monday, Thursday, Friday, and Sunday
- Estimated price
- $140–650
Flights from San Diego International Airport to General Mitchell International Airport via Denver
- Ave. Duration
- 6h
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $140–650
Flights from San Diego International Airport to General Mitchell International Airport via St. Louis
- Ave. Duration
- 6h 15m
- When
- Monday, Thursday, and Friday
- Estimated price
- $150–700
Flights from San Diego International Airport to General Mitchell International Airport via Chicago Midway International Airport
- Ave. Duration
- 7h 5m
- When
- Saturday
- Estimated price
- $140–650
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from San Diego to Fullerton Amtrak Station
- Ave. Duration
- 2h 19m
- Frequency
- Hourly
- Estimated price
- $25–60
- Website
- Amtrak
Train from Fullerton Amtrak Station to Chicago Union Station
- Ave. Duration
- 42h 47m
- Frequency
- Once daily
- Estimated price
- $550–1,300
- Website
- Amtrak
Train from Milwaukee to Chicago Union Station
- Ave. Duration
- 1h 29m
- Frequency
- Every 4 hours
- Estimated price
- $21–50
- Website
- Amtrak
.jpg "Pacific Surfliner interior")
- Phone
- +1 (855) 626-8585
- Website
- Flixbus USA
Bus from San Diego to Los Angeles Union Station
- Ave. Duration
- 2h 35m
- Frequency
- Twice daily
- Estimated price
- $18–28
- Schedules at
- Flixbus USA
Bus from St Louis Bus Station to Chicago Bus Station
- Ave. Duration
- 6h 5m
- Frequency
- Twice daily
- Estimated price
- $45–75
- Schedules at
- Flixbus USA
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.
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Booking & Getting There
San Diego to Chicago bus services, operated by Flixbus USA, arrive at Los Angeles Union Station.
Chicago is 2h ahead of San Diego. It is currently 4:59 PM in San Diego and 6:59 PM in Chicago.
San Diego to Chicago train services, operated by Amtrak, arrive at Fullerton Amtrak Station.
Yes, the driving distance between San Diego to Chicago is 2086 miles. It takes approximately 32h 39m to drive from San Diego to Chicago.
Book your San Diego to Chicago train tickets online with Omio.
Book your San Diego to Chicago bus tickets online with Omio and FlixBus.
There are 1280+ hotels available in Chicago.