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. Traveling with a dog or cat? View pet-friendly stops between San Diego and Chicago. Find the best hotels, restaurants, and attractions based on the most talked about places recommended by Trippy members.
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.
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.
Las Vegas (275 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
hotels around Las Vegas:
MGM Grand Las Vegas
Wynn Hotel Las Vegas
Mandalay Bay Resort and Casino
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 (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
Moab (33 answers)
Arches National Park (27 mentions)
Canyonlands National Park (17 mentions)
questions about Moab:
Seeking Dog Friendly Adventures in Moab?
Vail (52 answers)
restaurants around Vail:
hotels around Vail:
Vail Ski Resort
questions about Vail:
Outlet for ski clothing?
Summer Restaurants in Vail
North Platte (2 answers)
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
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?
Your final destination is Chicago, Illinois.
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 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:
Want to research more popular hotels in Chicago? Click the blue button below.
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:
Want to research more popular restaurants in Chicago? 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 Chicago.
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 San Diego well, please help your fellow travelers and answer their questions about San Diego!