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San Diego to Chicago drive

2 travelers   /   driving   /   5 days



San Diego to Chicago road trip planner

Here's a sample itinerary for a drive from San Diego to Chicago. If you're planning a road trip to Chicago, you can research locations to stop along the way. Find the best restaurants, hotels, and attractions based on the most talked about places recommended by Trippy members.

customize this trip
 Day 1

10:00 am  start in San Diego
drive for about 5 hours

3:48 pm  Las Vegas
stay overnight at Bellagio Hotel
leave the next day around 10:00 am

day 1 driving ≈ 5 hours
find more stops

 Day 2

10:00 am  leave from Bellagio Hotel
drive for about 2.5 hours

12:39 pm  Zion National Park
stay for about 1.5 hours and leave at 2:09 pm
drive for about 5.5 hours

7:38 pm  Arches National Park
stay overnight and leave the next day around 11:00 am

day 2 driving ≈ 8 hours
find more stops

 Day 3

11:00 am  leave from Arches National Park
drive for about 4.5 hours

3:25 pm  Vail
stay overnight at Vail Ski Resort
leave the next day around 9:00 am

day 3 driving ≈ 4.5 hours
find more stops

 Day 4

9:00 am  leave from Vail Ski Resort
drive for about 7.5 hours

4:17 pm  Hastings (Nebraska)
stay for about 1 hour and leave at 5:17 pm
drive for about 2.5 hours

7:48 pm  Omaha
stay overnight and leave the next day around 10:00 am

day 4 driving ≈ 10 hours
find more stops

 Day 5

10:00 am  leave from Omaha
drive for about 2 hours

11:58 am  Des Moines
stay for about 1 hour and leave at 12:58 pm
drive for about 5 hours

6:01 pm  arrive in Chicago
eat at Lou Malnati's Pizzeria
stay at The James Chicago Hotel

day 5 driving ≈ 7 hours
find more stops

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Enter a city to drive through on the way from San Diego to Chicago.
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Where does my trip begin?

Your starting point is San Diego, California.

You can enter an exact street address if you want to get precise directions, but this is optional.




How many cars do we need?

Since there are only 2 travelers, we assume you're driving 1 car. You can adjust the number of people traveling at the top. We assume a maximum of 4 passengers per car, but you can change the number of cars to fit your situation.




Where should I stop along the way?

Las Vegas  (262 answers)
    Downtown Container Park  (15 mentions)
    Fremont Street Experience  (15 mentions)
    High Roller  (10 mentions)
    The Mob Museum  (8 mentions)
    Neon Museum  (8 mentions)
    restaurants around Las Vegas:
        Giada
        Mon Ami Gabi
        Wicked Spoon
        Golden Nugget Hotel & Casino
        Lotus of Siam
    hotels around Las Vegas:
        Bellagio Hotel
        MGM Grand Las Vegas
        Wynn Hotel Las Vegas
        Mandalay Bay Resort and Casino
        The Cosmopolitan
    questions about Las Vegas:
        Best new restaurants in Vegas?
        What time of year is the best for scoring a cheap deals in Las Vegas
        Best tips and casinos for first time gambler?
        Is it better to stay on or off the Las Vegas strip?
        Top things to do in Las Vegas that don't include gambling?
Zion National Park  (70 mentions)
    questions about Zion National Park:
        When is the best time to visit/hike Zion national park?
        Canyoneer boots, Keen sandals, or old tennis shoes for Narrows hike?
        What's the best time of year to hike in Zion?
        Poisonous plants/ Venomous animals in Zion Canyon
        Are hiking boots necessary now if I hike Angels Landing
Arches National Park  (32 mentions)
Vail  (52 answers)
    restaurants around Vail:
        Minturn Saloon
    hotels around Vail:
        Vail Ski Resort
    questions about Vail:
        Outlet for ski clothing?
        Summer Restaurants in Vail
Hastings (Nebraska)  (2 answers)
    questions about Hastings (Nebraska):
        Places to go
Omaha  (16 answers)
    Henry Doorly Zoo  (8 mentions)
    Joslyn Art Museum  (3 mentions)
    Lauritzen Gardens  (2 mentions)
    The Durham Museum  (2 mentions)
    Omaha Children's Museum  (2 mentions)
    restaurants around Omaha:
        M's Pub
        Stokes Grill & Bar Wood Fired Foods
        801 Chophouse at The Paxton
        Lo Sole Mio Ristorante
    questions about Omaha:
        Best free things to do in Omaha?
        Low-key bachelor party activities in Omaha?
        Dog friendly hotels
Des Moines  (18 answers)
    questions about Des Moines:
        What's the best neighborhood in Des Moines for a first time visitor?
        Any good hiking spots in or near Des Moines?




Where does my trip end?

Your final destination is Chicago, Illinois.

You can enter the exact street address of your destination, but this is optional.




Where's the best place to stay in Chicago?

Are you going straight to a hotel, or looking for a vacation rental or Airbnb?

The best resource on neighborhoods, areas, and hotels is the Trippy page on where to stay in Chicago.

You can also see most people recommend as the best amount of time to visit. Find out how many days in Chicago to stay.

If you're looking for a quick answer, you can check out The James Chicago Hotel, which was mentioned 12 times on Trippy.

Here are some more hotels people talk about:

Hotel Palomar Chicago  (9 mentions)
Virgin Hotels Chicago  (8 mentions)
Thompson Chicago  (6 mentions)

Want to research more popular hotels in Chicago? Click the blue button below.






Where's the best place to eat in Chicago?

Need some recommendations on somewhere to get food?

Trippy members suggest Lou Malnati's Pizzeria, which was mentioned 36 times.

Here are some more restaurants people talk about:

Pequod's Pizza  (26 mentions)
Girl & the Goat  (24 mentions)
Big Star  (23 mentions)
Au Cheval  (17 mentions)

Want to research more popular restaurants in Chicago? Click the blue button below.






What are some things to do in Chicago?

This section could be endless, so rather than trying to suggest every local activity or attraction, we'll leave it open-ended.

These are some of the places people talk about on Trippy:

Millennium Park  (54 mentions)
Shedd Aquarium  (46 mentions)
Willis Tower  (38 mentions)
Lincoln Park Zoo  (35 mentions)

Of course, Trippy is the perfect place to ask questions because there's an entire community of travelers talking to each other and sharing tips and advice. Trippy is where you can get answers personalized for your tastes, budgets, trip dates & more!

For example, here are some questions people have asked about Chicago. Click on any question to see answers from the community!

 Sunil Gupta from Mountain View asked:
Best Chicago pizza?  (18 answers)

 Katie Simons from Los Angeles asked:
What is your favorite restaurant in Chicago?  (15 answers)

 Blair Cabot from Halifax asked:
What to do in one weekend in Chicago?  (14 answers)

 지은 기 from asked:
airport transportation  (14 answers)

 Stacey Wall from Jackson, Mississippi asked:
What are the coolest hotels in downtown Chicago?  (12 answers)

Click the button below to explore more questions and answers related to Chicago.






Do I really have to go back home?

Yes, even this step is optional, because if you're on vacation who wants the trip to end? It's okay, you can start planning your next trip!

Want to plan the trip back? Get the reverse directions for a Chicago to San Diego drive, or go to the main page to plan a new road trip.

You can also compare the travel time if you're flying or driving by calculating the distance from San Diego to Chicago. Or get a full San Diego to Chicago flight plan.

Don't forget about exploring your own hometown with a staycation. You can also find some cool day trips or get away for a weekend. Maybe try typing in a faraway location like London, Hong Kong, or Sydney, and get inspired for your dream trip around the world.

And if you know San Diego well, please help your fellow travelers and answer their questions about San Diego!






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At a Glance
without making any stops
total driving distance is 2,077 miles
driving time of 29 hours, 23 minutes
Chicago is 2 hours ahead of San Diego
214 San Diego travel answers
262 Las Vegas travel answers
52 Vail travel answers
2 Hastings (Nebraska) travel answers
16 Omaha travel answers
18 Des Moines travel answers
260 Chicago travel answers





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