Next departures from San Diego to Chicago on 21 November
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
FlixBus + Greyhound Lines, Inc.
Bus
Downtown SD (Seaport)
Chicago 95Th & Dan Ryan
Cheapest
FlixBus + Greyhound Lines, Inc.
Bus
UCSD Health La Jolla Station
Downtown Greyhound Station
Fastest
FlixBus + Greyhound Lines, Inc.
Bus
San Diego (Old Town-FlixBus)
Downtown Greyhound Station
No tags
Bus
Greyhound Bus Stop
Downtown Greyhound Station
No tags
FlixBus + Greyhound Lines, Inc.
Bus
San Diego (Old Town-FlixBus)
Downtown Greyhound Station
No tags
Next departures from San Diego to Chicago on 22 November
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
FlixBus + Greyhound Lines, Inc.
Bus
San Diego (Old Town-FlixBus)
Chicago 95Th & Dan Ryan
Cheapest
FlixBus + Greyhound Lines, Inc.
Bus
UCSD Health La Jolla Station
Downtown Greyhound Station
Fastest
FlixBus + Greyhound Lines, Inc.
Bus
San Diego (Old Town-FlixBus)
Downtown Greyhound Station
No tags
Bus
Greyhound Bus Stop
Downtown Greyhound Station
No tags
FlixBus + Greyhound Lines, Inc.
Bus
San Diego (Old Town-FlixBus)
Downtown Greyhound Station
No tags
Next departures from San Diego to Chicago on 23 November
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
FlixBus + Greyhound Lines, Inc.
Bus
UCSD Health La Jolla Station
Chicago 95Th & Dan Ryan
Cheapest
FlixBus + Greyhound Lines, Inc.
Bus
UCSD Health La Jolla Station
Downtown Greyhound Station
Fastest
FlixBus + Greyhound Lines, Inc.
Bus
San Diego (Old Town-FlixBus)
Downtown Greyhound Station
No tags
Bus
Greyhound Bus Stop
Downtown Greyhound Station
No tags
FlixBus + Greyhound Lines, Inc.
Bus
San Diego (Old Town-FlixBus)
Downtown Greyhound Station
No tags
Next departures from San Diego to Chicago on 24 November
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
FlixBus + Greyhound Lines, Inc.
Bus
Downtown SD (Seaport)
537-517 W. Jackson Blvd
Cheapest
FlixBus + Greyhound Lines, Inc.
Bus
UCSD Health La Jolla Station
Downtown Greyhound Station
Fastest
FlixBus + Greyhound Lines, Inc.
Bus
San Diego (Old Town-FlixBus)
Downtown Greyhound Station
No tags
Bus
Greyhound Bus Stop
Downtown Greyhound Station
No tags
FlixBus + Greyhound Lines, Inc.
Bus
San Diego (Old Town-FlixBus)
Downtown Greyhound Station
No tags
Next departures from San Diego to Chicago on 25 November
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
FlixBus + Greyhound Lines, Inc.
Bus
San Diego (Old Town-FlixBus)
Downtown Greyhound Station
Cheapest
FlixBus + Greyhound Lines, Inc.
Bus
UCSD Health La Jolla Station
Downtown Greyhound Station
Fastest
FlixBus + Greyhound Lines, Inc.
Bus
San Diego (Old Town-FlixBus)
Downtown Greyhound Station
No tags
Bus
Greyhound Bus Stop
Downtown Greyhound Station
No tags
FlixBus + Greyhound Lines, Inc.
Bus
San Diego (Old Town-FlixBus)
537-517 W. Jackson Blvd
No tags
Next departures from San Diego to Chicago on 26 November
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Greyhound Lines, Inc. + FlixBus
Bus
Greyhound Bus Stop
Chicago 95Th & Dan Ryan
Cheapest
FlixBus + Greyhound Lines, Inc.
Bus
UCSD Health La Jolla Station
Downtown Greyhound Station
Fastest
FlixBus + Greyhound Lines, Inc.
Bus
San Diego (Old Town-FlixBus)
Downtown Greyhound Station
No tags
Bus
Greyhound Bus Stop
Downtown Greyhound Station
No tags
FlixBus + Greyhound Lines, Inc.
Bus
San Diego (Old Town-FlixBus)
Downtown Greyhound Station
No tags
Next departures from San Diego to Chicago on 27 November
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
FlixBus + Greyhound Lines, Inc.
Bus
UCSD Health La Jolla Station
Chicago 95Th & Dan Ryan
Cheapest
FlixBus + Greyhound Lines, Inc.
Bus
UCSD Health La Jolla Station
Downtown Greyhound Station
Fastest
FlixBus + Greyhound Lines, Inc.
Bus
San Diego (Old Town-FlixBus)
Downtown Greyhound Station
No tags
Bus
Greyhound Bus Stop
Downtown Greyhound Station
No tags
FlixBus + Greyhound Lines, Inc.
Bus
San Diego (Old Town-FlixBus)
Downtown Greyhound Station
No tags
Next departures from San Diego to Chicago on 28 November
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
FlixBus + Greyhound Lines, Inc.
Bus
San Diego (Old Town-FlixBus)
Downtown Greyhound Station
Cheapest
FlixBus + Greyhound Lines, Inc.
Bus
UCSD Health La Jolla Station
Downtown Greyhound Station
Fastest
FlixBus + Greyhound Lines, Inc.
Bus
San Diego (Old Town-FlixBus)
Downtown Greyhound Station
No tags
Bus
Greyhound Bus Stop
Downtown Greyhound Station
No tags
FlixBus + Greyhound Lines, Inc.
Bus
San Diego (Old Town-FlixBus)
Downtown Greyhound Station
No tags
Last refresh of the prices: Yesterday at 19:17 PST.
Compare 2 ways to travel from San Diego to Chicago
We recommend taking the train
Among the sustainable travel choices, the train stands out as a good way to reach Chicago. The journey takes about 1 day, 22 hours 41 minutes and with fares starting at just £146, it presents an excellent value for a comfortable ride.
Based on 87387 reviews, the company was rated 3.5 stars on Busbud. Travellers were especially satisfied with the ticket access and the temperature but often complained with the Wi-Fi. Greyhound ticket prices on this trip start at £89
Based on 5597 reviews, the company was rated 4.1 stars on Busbud. Travellers were especially satisfied with the seats and the ticket access but often complained with the Wi-Fi. Amtrak ticket prices on this trip start at £245
Based on 11388 reviews, the company was rated 3.5 stars on Busbud. Travellers were especially satisfied with the ticket access and the staff but often complained with the Wi-Fi. FlixBus ticket prices on this trip start at £97
Frequently asked questions about travelling by bus from San Diego, CA, US to Chicago
What's the distance between San Diego and Chicago by coach?
The journey from San Diego to Chicago by coach covers an approximate distance of 1729 miles (2788 km).
How can I travel from San Diego to Chicago avoiding air travel?
To travel from San Diego to Chicago without flying, you can take the coaches. The coach provides a comfortable and sustainable journey and allows you to enjoy the sights while reaching your destination. You might also find carpooling options to travel between the two cities.
Find cheapest prices for buses
Price is for a one-way ticket for one passenger and based on past searches.
Best price found
19/11
£357
20/11
£451
Today
£447
22/11
£370
23/11
£285
24/11
£304
25/11
£291
26/11
£285
The cheapest trip from San Diego, CA, US to Chicago was searched and found on 23 Nov 2025 with a price of £285
To save money and be sure you have the best seat, it's a good idea to buy your bus tickets from San Diego, CA, US to Chicago as early as possible.
You can expect to pay from £285 to £467 for a bus ticket from San Diego, CA, US to Chicago based on the last 2 days. You can expect to find the cheapest price for the trip at £285, which is on 2025-11-23.
What's the cheapest way to go from San Diego, CA, US to Chicago?
The bus is the cheapest travel choice for this destination
The cheapest trip from San Diego, CA, US to Chicago was searched and found on 23 Nov 2025 with a price of £285
The bus is the cheapest travel choice for this destination
