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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
to
Chicago, United States

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

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
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
🛫 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
Useful tips for plane travellers
• Consider booking your flight on Southwest Airlines, as they frequently offer direct flights from San Diego to Chicago Midway and allow two free checked bags, which can be a significant cost saving if you're traveling with more luggage.
• Upon landing at Chicago Midway Airport, navigate to the 'Ground Transportation' area where you'll find clear signage for taxis and rideshare services; expect to pay approximately $30 to $40 for a taxi ride to downtown Chicago, depending on traffic.
• Be aware of potential weather changes; Chicago can be chilly and windy, so pack a light jacket even in summer months, and check Southwest Airlines’ website for any updates on your flight and baggage policies: southwest.com
🚌 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 2803.5 km by air and 3362.4 km by road. The typical travel time by plane is around 5 hours and 39 minutes. By car, it takes approximately 32 hours and 19 minutes to travel between the two cities.
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 ticket prices range from $70-$460.
The prices for train tickets between San Diego and Chicago can range from $115 to $834, depending on factors such as the class of travel and how far in advance the ticket is booked. Similarly, bus prices for the route can vary between $247 and $516.
To get from San Diego to Chicago without using public transportation, you can opt to drive. The road distance is approximately 3361.9 km, and it takes roughly 32 hours and 19 minutes to complete the journey by car. However, it is important to note that the prices for the trip can vary between $370 and $550 depending on various factors such as gas prices, tolls, and overnight stays if necessary.
The best way to travel from San Diego to Chicago without a car is by bus, which takes approximately 2 days and 3 hours and costs between $240 and $550. Another option is to fly, which takes 5 hours and 39 minutes and costs between $70 and $460. If you prefer to take the train, it will take approximately 2 days and 17 hours and cost between $110 and $850.
Yes, there is a direct link between San Diego and Chicago. However, the direct link is not available through train or bus services. For train travel, you can take an Amtrak train from San Diego to Chicago with transfers in Los Angeles, and the journey takes approximately 2 days and 17 hours. For bus travel, you can take either Greyhound or Flixbus from San Diego to Chicago with transfers in Los Angeles and St. Louis, and the journey takes approximately 2 days and 3 hours.
The flight between San Diego and Chicago typically takes around 3 hours and 50 minutes. However, the duration may vary depending on the airline and the specific flight. As for the cost, it can range from $73 to $460, depending on factors such as the airline, the time of booking, and any additional services or amenities chosen.
There are plenty of options for accommodation near Chicago. With over 1116 hotels available, visitors have a wide range of choices to suit their preferences and budget. Prices start at $58 per night, but rates can vary based on the location, amenities, and season.