Here's a sample itinerary for a drive from Chicago to San Diego. If you're planning a road trip to San Diego, you can research locations to stop along the way. Traveling with a dog or cat? View pet-friendly stops between Chicago and San Diego. Find the best hotels, restaurants, and attractions based on the most talked about places recommended by Trippy members.
Your starting point is Chicago, Illinois.
You can enter an exact street address if you want to get precise directions, but this is optional.
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.
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?
Omaha (17 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:
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
North Platte (2 answers)
Denver (150 answers)
Denver Museum of Nature and Science (15 mentions)
Denver Botanic Gardens (12 mentions)
Denver Art Museum (11 mentions)
LoDo (11 mentions)
Red Rocks Park and Amphitheatre (11 mentions)
restaurants around Denver:
Euclid Hall Bar & Kitchen
hotels around Denver:
The Brown Palace Hotel & Spa in Denver
The Crawford Hotel
Four Seasons Hotel Denver
the Curtis Denver - a DoubleTree by Hilton Hotel
questions about Denver:
Short, scenic drives from Denver?
Best resort for advanced skier?
Activites to do with children ages 7-11
Top 5 must see attractions in Denver?
Restaurant for dinner near Coors Field?
Moab (33 answers)
Arches National Park (27 mentions)
Canyonlands National Park (17 mentions)
questions about Moab:
Seeking Dog Friendly Adventures in Moab?
Zion National Park (73 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
Las Vegas (273 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:
Mon Ami Gabi
Golden Nugget Hotel & Casino
Lotus of Siam
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?
Your final destination is San Diego, California.
You can enter the exact street address of your destination, but this is optional.
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 San Diego.
If you're looking for a quick answer, you can check out Hotel Del Coronado, which was mentioned 28 times on Trippy.
Here are some more hotels people talk about:
Want to research more popular hotels in San Diego? Click the blue button below.
Need some recommendations on somewhere to get food?
Trippy members suggest The Prado at Balboa Park, which was mentioned 10 times.
Here are some more restaurants people talk about:
Want to research more popular restaurants in San Diego? Click the blue button below.
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:
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!
Click the button below to explore more questions and answers related to San Diego.
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!
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 Chicago well, please help your fellow travelers and answer their questions about Chicago!