Next departures for San Diego to Chicago on November 15
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 for San Diego to Chicago on November 16
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 for San Diego to Chicago on November 17
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
Downtown Greyhound Station
CheapestFastest
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
Bus
Greyhound Bus Stop
537-517 W. Jackson Blvd
No tags
Next departures for San Diego to Chicago on November 18
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 for San Diego to Chicago on November 19
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Bus
Greyhound Bus Stop
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
537-517 W. Jackson Blvd
No tags
FlixBus + Greyhound Lines, Inc.
Bus
San Diego (Old Town-FlixBus)
Downtown Greyhound Station
No tags
Next departures for San Diego to Chicago on November 20
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 for San Diego to Chicago on November 21
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
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 8:29 PM PST.
Compare 2 ways to go from San Diego to Chicago
We recommend taking the bus
Among the sustainable travel choices, the bus stands out as the good way to reach Chicago. The journey takes about 2 days, 6 hours 35 minutes and with fares starting at just $120, it presents an excellent value for a comfortable ride.
Greyhound Lines offers the most comprehensive intercity bus services in the United States. They operate a modern, environmentally friendly fleet that serves more than 2400 destinations and carries nearly 16 million passengers annually. When traveling with them, you can expect free WiFi, onboard entertainment, bathrooms, power outlets and decent legroom. One of the great perks of Greyhound is that they connect big cities and smaller towns in the US, where you usually can't get to by train or plane. If you're looking for safe and affordable transportation, Greyhound is a great choice.
Based on 5584 reviews, the company was rated 4.1 stars on Busbud. Travelers were especially satisfied with the seats and the ticket access but often complained with the wifi. Amtrak ticket prices on this trip start at $312
Flixbus is a European bus operator that offers intercity and bus travel in over 38 countries. Known for their easy-to-spot lime green buses and for offering affordable transportation between cities in Europe and the Americas, Flixbus is a good option for those looking for an affordable, reliable bus company. In their buses, you'll find free WiFi, bathrooms, and power outlets. You can also pay extra to choose your seat and get extra legroom, or even buy a snack or drink onboard directly from the driver. You can reschedule your ticket for a small fee, which varies from $1 to $5, depending on how close you are to the departure date.
Frequently asked questions about traveling from San Diego, CA, US to Chicago by bus
How far is San Diego from Chicago?
San Diego and Chicago are 1729 miles (2788 km) apart.
What are the departure and arrival stations when taking the bus from San Diego to Chicago?
Most of the buses traveling from San Diego to Chicago leave from Mission Valley Sheraton and arrive at Downtown Greyhound Station. These are the primary departure and arrival locations on this route, but you can find others that could fit better into your travel plans.
What are the best sights and things to do in Chicago?
Once in Chicago, you can start exploring the city and discover its surroundings. The top sights and things to do are Museum of Science and Industry, Lincoln Park Conservatory, Architectural River Cruise, Willis Tower (Sears Tower) and Shedd Aquarium.
Find cheapest prices for buses
Price is for a one-way ticket for one passenger and based on past searches.
Best price found
11/12
$388
11/13
$446
Today
$498
11/15
$440
11/16
$260
11/17
$386
11/18
$316
11/19
$280
The cheapest trip from San Diego, CA, US to Chicago was searched and found on Nov 16, 2025 with a price of $260
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 $260 to $574 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 $260 which is on 2025-11-16.
What's the cheapest way to go from San Diego, CA, US to Chicago?
The bus is the cheapest travel choice for this destination