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San Diego, CA, USA to Chicago, IL, USA from $78: 5 ways by bus, train, flight or car

Compare Travel Options and Prices

from
San Diego, United States of America
to
Chicago, United States of America

How to Get from San Diego to Chicago: Cheapest, Fastest and Best Way

1Map provides directions to cities, towns, landmarks, attractions, and addresses worldwide, offering thousands of multi-modal routes to easily get you from point A to point B.

$78 - PlaneBest price
3362 kmDistance
5h 42m Fastest

Compare Train, Bus, Flight, and Driving Options

Get detailed, step-by-step directions below for your trip from San Diego to Chicago with 1Map travel planner. Easily compare ticket prices, explore various transport options, and find the best routes for a seamless and cost-effective travel experience.

Company
Various
Plane
Average Duration
5h  42m
Estimated price
$78-610
Recommended
route map
Distance: 3362 km
Duration: 5h 42m

See more options

Company
Various
Bus
Average Duration
48h  2m
Estimated price
$0-0
Company
Various
Plane
Average Duration
5h  53m
Estimated price
$78-480
Company
Amtrak
Train
Average Duration
49h  17m
Estimated price
$115-834
Company
Various
Drive
Average Duration
32h  19m
Estimated price
$370-550

Traveling From San Diego to Chicago

Traveling from San Diego to Chicago offers a striking contrast between San Diego's laid-back coastal lifestyle and Chicago's vibrant urban energy.

Best Neighbourhoods in Chicago

Chicago’s neighborhoods each offer distinct charm and character for visitors.

Wicker Park
• Known for its trendy shops and cafes.
• Vibrant art scene and music venues.
Lincoln Park
• Home to beautiful parks and the zoo.
• Great dining options and boutiques.
The Loop
• Chicago’s central business district and skyline views.
• Iconic architecture and cultural attractions.

Best Times To Visit Chicago's Attractions

Timing your visits to Chicago's attractions can elevate your experience.

Millennium Park
Visit early morning on weekdays for fewer crowds and stunning views.
The Art Institute of Chicago
Seek afternoons or late evenings, especially during free admission days.
Navy Pier
Go on weekdays or in the early hours for a relaxing stroll.

Chicago Weather: What to Expect Year-Round

Chicago experiences a diverse climate with hot summers and cold winters, making spring and fall the best times to explore the city. Weather can greatly influence your travel plans, so being prepared for sudden changes ensures you enjoy everything from outdoor festivals to indoor attractions.

Dining Recommendation

Indulge in Chicago's iconic deep-dish pizza at Lou Malnati's, where the rich, buttery crust and hearty layers of cheese and toppings create a comforting experience distinct from San Diego's fresh seafood and tacos. The bustling atmosphere and dedication to local ingredients make every bite a flavorful reminder of Chicago's vibrant culinary scene.

San Diego - Chicago operators

Explore transport companies operating between San Diego and Chicago, with prices starting at . These companies offer competitive pricing, flexible schedules, and comfortable travel experiences.

Plane
Website
southwest.com

Plane from San Diego (SAN) to Chicago Midway (MDW)

Average Duration
5h 42m
Estimated price
$78-610

Plane from San Diego (SAN) to Chicago O'Hare (ORD)

Average Duration
5h 53m
Estimated price
$78-480
Website
united.com

Plane from San Diego (SAN) to Chicago O'Hare (ORD)

Average Duration
4h 1m
Estimated price
$785-786
Website
aa.com

Plane from San Diego (SAN) to Chicago O'Hare (ORD)

Average Duration
4h 7m
Estimated price
$785-781
Bus
Contact phone
+1 800-872-7245
Website
amtrak.com

Bus from Santa Fe Depot, CA to Chicago Bus Station

Average Duration
48h 2m
Estimated price
0-0
Contact phone
+1 214-849-8100
Website
greyhound.com

Bus from Santa Ana Bus Stop to Las Vegas S Strip Transit Terminal

Average Duration
5h 45m
Estimated price
$4805-75

Bus from Las Vegas S Strip Transit Terminal to St Louis Bus Station

Average Duration
33h 15m
Estimated price
$61000-6108

Bus from St Louis Bus Station to Chicago Bus Station

Average Duration
6h 39m
Estimated price
$6104-788
Train Show train routes
Contact phone
+1 800-872-7245
Website
amtrak.com

Train from San Diego to Los Angeles

Average Duration
2h 56m
Estimated price
$787-788

Train from Los Angeles to Chicago Union Station

Average Duration
49h 13m
Estimated price
$780-750

San Diego to Chicago: Overview of Bus, Train, Flight, and Car Trips

Traveling between San Diego and Chicago offers a variety of convenient options to suit your preferences, schedule, and budget. Whether you prioritize affordability, speed, or comfort, you’re sure to find the perfect way to travel without compromising on quality or convenience.

🚗 Embark on an epic road trip from sunny San Diego to vibrant Chicago spanning over 2089 miles. The journey offers a blend of breathtaking landscapes and diverse cities along the way. 💸 Travel costs to reach Chicago from San Diego by car can range from $370 to $550, giving flexibility to choose accommodations and dining options to suit your budget. Enjoy the freedom of the open road as you make your way through scenic routes and charming towns. 🌆 Arrive in Chicago after approximately 32 hours and 19 minutes of driving, ready to explore the iconic architecture, world-class museums, and deep-dish pizza that the Windy City has to offer. Your cross-country adventure promises unforgettable memories and the thrill of discovering new destinations.
Average price
$370 - $550
🚆 Starting your journey from sunny San Diego to the bustling city of Chicago by train will be an exciting adventure with a total travel time of approximately 2 days and 17 hours. Despite the absence of a direct route, the trip will take you through picturesque landscapes and vibrant cityscapes. 🚆 The Amtrak services will first take you from San Diego to Los Angeles before connecting you to the train bound for Chicago Union Station. With a distance of 2,845 miles, you'll have the opportunity to relax and enjoy the scenic views throughout your journey. Be prepared for the transfer process, but rest assured that the friendly Amtrak staff will assist you every step of the way. 🚆 While the prices for a ticket on this route can range from $115 to $834, the experience of traveling by train from the West Coast to the Midwest is undoubtedly worth it. Embrace the slower pace of train travel, unwind in your comfortable seat, and anticipate the moment when you'll arrive at the iconic Chicago Union Station, ready to explore all that the Windy City has to offer.
Departure Point
San Diego station
Arrival Point
Chicago Union Station
Useful tips for train travellers
• On your train journey from San Diego to Chicago, you’ll likely be traveling with Amtrak, which offers a variety of onboard services. Amtrak provides a café car with limited catering options, including sandwiches, snacks, and beverages. Additionally, if you book a sleeper car, meals are generally included and served in your room or in the dining car.
• For seating options on Amtrak trains, you have several classes to choose from: Economy Class features spacious seating but no additional amenities. Business Class offers more comfort and may include complimentary non-alcoholic beverages. First Class seats in the sleeper cars offer the most luxury along with private accommodations. Check Amtrak's website for more details on seating arrangements: amtrak.com
• Upon arriving in Chicago, you will likely disembark at Union Station, the city’s main train station. It's essential to note that Union Station does not provide a luggage storage service, so plan to carry your bags with you. The restrooms are available in the station, but showers are not. For the fastest route to the city center, board the ‘L’ train Blue Line from the adjacent station. It’s a direct route to downtown Chicago, with a travel time of about 30 minutes.
🛫 Embark on an efficient journey from San Diego to Chicago by taking the convenient direct flight offered by Southwest Airlines. In just 3 hours and 50 minutes, you'll arrive at Chicago Midway Airport, ready to explore the Windy City. 🌆 Enjoy a smooth and comfortable flight experience as you traverse approximately 1,731 miles from the sunny West Coast to the bustling Midwest. With a flight duration of 5 hours and 42 minutes, sit back, relax, and anticipate the diverse adventures awaiting you in Chicago. 💸 Explore various pricing options for your flight between San Diego and Chicago, ranging from $78 to $610. Whether you're seeking budget-friendly fares or prefer added amenities, there's a flight option tailored to your preferences for this exciting transcontinental journey.
Departure Point
San Diego Airport
Arrival Point
Chicago Midway Airport
🚌 Starting from San Diego your bus journey to Chicago USA will encompass multiple transfers, taking approximately 2 days and 2 hours. The route involves stops at Santa Ana, Las Vegas, and St Louis before reaching your destination at the Chicago Bus Station.
Departure Point
Santa Fe Depot, CA station
Arrival Point
Chicago Bus Station

Frequently asked questions

Find out more about the route from San Diego to Chicago.

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The distance between San Diego and Chicago is approximately 1742 miles by air. The typical travel time by plane is around 5 hours and 39 minutes. If you prefer to travel by car, the road distance is longer at 2089 miles and it normally takes approximately 32 hours and 19 minutes to reach Chicago from San Diego. There is no information provided for train or bus travel times.
The most cost-effective and time-efficient transportation option for traveling from San Diego to Chicago is by flying. It takes approximately 5 hours and 39 minutes and the cost ranges from $70 to $460. Flying not only provides the fastest travel time but also offers competitive pricing, making it the best choice for those looking for convenience and affordability.
The prices for a train journey between San Diego and Chicago range from $115 to $834. Alternatively, taking a bus from Chicago to San Diego has prices that vary between $247 and $516. These prices can fluctuate depending on factors such as time of travel, class of service, and availability. It is advisable to check with the specific train or bus operator for the most accurate and up-to-date prices.
To travel from San Diego to Chicago without using public transportation, your best option would be to drive. The driving distance between the two cities is approximately 2089 miles, and it would take approximately 32 hours and 19 minutes to complete the journey. The prices for a car trip from San Diego to Chicago can vary from $370 to $550, depending on factors such as gas prices and any additional fees or accommodations along the way.
The best way to travel from San Diego to Chicago without a car is by bus, which takes approximately 2 days and 3 hours. This option is cost-effective, with fares ranging from $240 to $550. Another option is to fly, which takes about 5 hours and 39 minutes with fares ranging from $70 to $460. If you prefer a longer and more scenic journey, you can take a train, which takes approximately 2 days and 17 hours and costs between $110 and $850.
Yes, there are indirect transportation options available between San Diego and Chicago. If traveling by train, you would need to take a train from San Diego to Los Angeles, and then transfer to a train that goes from Los Angeles to Chicago Union Station, with a total travel time of approximately 2 days and 17 hours. If traveling by bus, you would need to take a bus from San Diego to Los Angeles, then transfer to another bus that goes from Los Angeles to St Louis, and finally transfer to a bus that goes from St Louis to Chicago, with a total travel time of approximately 2 days and 3 hours.
The flight from San Diego to Chicago typically takes around 3 hours and 50 minutes. However, the exact duration may vary depending on factors such as weather conditions and air traffic. As for the cost, prices for flights between Chicago and San Diego can range from $73 to $460, depending on variables such as the airline, time of booking, and availability. It is always advisable to check with different airlines and compare prices to get the best deal.
There are numerous options for accommodation in Chicago with over 1116 hotels available. Prices for hotels in the area start at $58 per night. From luxury hotels to budget-friendly options, travelers can find a wide range of choices to suit their preferences and budgets. It is recommended to research and compare different hotels based on location, amenities, and customer reviews to find the best option for your stay in Chicago.

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