✨ Thatch is moving to Mindtrip! Learn More
Chicago: The Ultimate Day Trip

Chicago: The Ultimate Day Trip

JackxJo
If you are looking to visit the city of Chicago, look no further! The third largest city in the country is worth exploring whether you only have one day or an entire week. This guide will provide you with an exact itinerary for an overnight trip as well as countless recommendations of the best things to do if the exact itinerary doesn't fit your needs. This guide also provides information on how to visit Indiana Dunes National Park, which sits just an hour away from Chicago by train.
Updated ago
1
Share

The Windy City 

Chicago is one of the best cities in the United States to visit for a weekend. While there are enough restaurants, museums, and attractions in this city to keep you occupied for a full week, you can hit all of the highlights in an overnight trip. Despite being the 3rd largest city in the country, it is extremely to easy to get around within Chicago. It has fantastic public transport that will get you to most of the cities main attractions and is otherwise very walkable. If you're looking for a quick getaway that features good food, natural beauty, and the big city, then this is the trip for you.

Best Places to Stay:

River North/Streeterville

Embassy Suites by Hilton Chicago Downtown River North
@JackxJo
Add to
Details
21c Museum Hotel Chicago
@JackxJo
Add to
Details
The Westin Chicago River North
@JackxJo
Add to
Details
The Godfrey Hotel Chicago
@JackxJo
Add to
Details

Buy to unlock full guide

Access all the local insights and recommendations from @JackxJo when you purchase this guide.
ABOUT THE AUTHOR
JackxJo
Hey! We’re Jack and Jordan, the creators of JackxJo, and we’re here to help you unlock the world of travel—even if you think you don’t have the time or the budget for it. We are both college students at the University of Texas at Austin who have been exploring the U.S. together for three years. Being in college has made us learn how to travel efficiently both with our time and finances. We believe in honest and impactful advice. We’ve juggled busy schedules and tight budgets, but we’ve figured out how to make travel work without the stress. Our guides focus on the practical tips that actually matter: where to stay, where to eat, and what to do. Between the two of us, we’ve covered a lot of ground, and we’re constantly sharing our latest discoveries. From national parks to small towns, we’re always on the lookout for the next adventure. We’re also big believers in making travel accessible for everyone, so whether you’re a college student planning your first trip or someone looking for a quick escape from the daily grind, our guides will help you travel smarter, not harder.
What's included
Digital Map
Fully interactive, digital map for finding places nearby
63 places
63 hand-picked places with notes from the creator
11 photos
Beautiful, hi-res photos from the creator
5 links
5 links from the creator to go even deeper with more info
DESTINATION(S) COVERED
Indiana Dunes National Park, Porter, IN, USA
Illinois, USA
Indiana, USA
Indiana Dunes State Park, North 25 East, Chesterton, IN, USA
Chicago, IL, USA
FOCUSES AND THEMES
50+
Accessibility
Business
Couples
Car-free
Digital Nomads
Family
Groups
Adventure
Architecture
Art
Budget
Coffee
Foodie
History
Outdoors
People & Culture
Photography
Shopping
BEST TIME OF YEAR
JAN
FEB
MAR
APR
MAY
JUN
JUL
AUG
SEP
OCT
NOV
DEC
Format
Itinerary
Itineraries typically include day-by-day plans, with food, lodging and activity recommendations for each day.
COMMON QUESTIONS
What is Thatch?
Thatch is an online marketplace that provides instant access to thousands of vetted local experts and premium travel guides - making it the easiest and most affordable way to take high quality trips with less stress. For travel creators (tastemakers, travel advisors, influencers and local experts) Thatch makes it easy to curate, publish, and sell digital travel guides, itineraries and personalized planning services.
What if I’m not satisfied with my purchase?
How do I access my purchased guides?
Can I access my guide offline?
How often are guides updated?
Can I request a personalized guide or itinerary?
Can I sell my own travel guides and itineraries?
Save for Later
Share
Powered by Thatch
The home for unique & authentic travel
Powered by Thatch: Where great trips are made.
© JackxJo 2025 Help Privacy Terms Copyright Become a Seller Seller Academy About Careers Blog Explore Places