Results for Chicago, IL, USA
Complete guide about Chicago.
Main attractions, where to eat, and even where to sleep.
How many days you want to explore this city is up to you.
50+ • Accessibility • Business • Car-free • Couples • Digital Nomads • Family • Gluten-free / Celiac • Groups • LGBTQ+ • Plus Size • Female Solo • Vegan • Vegetarian • Adventure • Architecture • Art • Boutique • Coffee • Design • Foodie • History • Luxury • Outdoors • People & Culture • Photography • Relaxation • Romantic • Shopping • Slow Travel • Wellness
$35.00
0
What are your top 3 dream travel destinations? Do they seem like just dreams to you? What if you could make them happen with a little bit of help?
Hi, I'm Alyssa, and I am one of those weird people who's favorite activity is planning trips. After many years of traveling the world, I love sharing what I've gleaned from my travels with my clients to help them plan their dream trip.
With 15 different countries traveled, I can offer you expertise to plan your trip according to your budget, travel style, personal preferences, and timeline. I have four different packages, depending on how much you'd like me to do and how much you'd like to do yourself.
Places I specialize in...
- Turkey
- Germany
- Switzerland
- Israel
- Montenegro
- Cyprus
- Greece
- Budapest, Hungary
- Prague, Czech Republic
- Chicago, Illinois, USA
- London, UK
- Amsterdam, Netherlands
(P.S. This list does not mean you're limited to these destinations! I would love to explore different places with you.)
Want to make your travel dreams come true? Keep scrolling to see how it works and what option might best fit your travel needs.
Adventure • Foodie • Faith • History • Shopping • Budget • Nature • People & Culture • Romantic • Photography • Road Trip • Wine • Coffee • Beach • Mountain • Relaxation
Free
0
Our quick take on every restaurant/cafe/bar/bakery we visit in NYC, updated as we go (plus a score for El Prez).
Tips/tricks/suggestions provided for all types of situations (e.g., reservation requirements, best order options, pics, pricing, etc.). Newest reviews at the top of the list.
This is a combination of some well-known spots, holes in the wall, late night bites, and neighborhood gems across the city (predominantly Manhattan & Brooklyn).
PRO TIP: If you want to search for the best spots according to us, just 'CMND/CTRL + F' for "8." or "9."
Foodie • Coffee • Wine
$5.00
5
The windy city, known for great food and incredible architecture, has so much to offer any visitor. This itinerary is completely walkable, with beautiful views all along the way.
Family • Car-free • Couples • LGBTQ+ • Female Solo • 50+ • Adventure • Architecture • Photography • Romantic • Foodie
Free
4
Chicago is a great city with awe-inspiring architecture, delicious food, and famous attractions to fill any trip. This first-timer's guide is here to help you navigate the city's must-see sights, ensuring you make the most of your Windy City adventure.
Couples • Family • Groups • Adventure • Architecture • Art • Foodie • People & Culture
Free
3
Ani Danelz | National Park Guide
Available for hire
How to Visit: Cuyahoga Valley and Indiana Dunes National Parks
This guide is for travelers looking to visit Cuyahoga Valley and/or Indiana Dunes National Parks.
These parks are about four and a half hours apart, so while it could be done in a long weekend, it might be better suited for individual trips or part of a longer road-trip.
Total trip time: 1 day (Cuyahoga Valley) + 1 day (Indiana Dunes)
Nearest major cities to start from:
- Ohio: Akron, Cleveland
- Indiana: Fort Wayne
- Illinois: Chicago
Accessibility • Family • Groups • Couples • Female Solo • Adventure • Budget • Camping • Outdoors • Relaxation • Road Trip • Van Life
Free
3
Ever contemplated a new method of travel? A way to break up all of the traffic-filled roadtrips or miserable treks to the airport, only to wait 2-3 hours for a flight? Fed up with the same old highway views (or lack of views from the plane)?
If so, this guide is for you! From the very first time I boarded an Amtrak Long Distance (LD) train in 2016 in Oakland, CA, I was immediately overcome with excitement, which quickly morphed into a passion. I have yet to go on a trip and not catch myself in a trance staring out the window on multiple occasions, failing to read/watch all of the books/shows I thought I would need or having a deep conversation with a complete stranger in the observation car. These experiences are the reason why I write this guide, to share and hopefully inform prospective travelers.
If you are not familiar with Amtrak’s LD services, fear not! I intend to offer as much information about the train options, destinations, schedules and anything else I can think of to lead your potential adventure. If for some reason, I don’t cover something, feel free to reach out!
This is just part one of a three-part guide and will cover the intro as well as the first five long-distance trains (numerically). Be sure to check out the other two sections, the individual more in-depth route guides, as well as 20 Questions for an Amtrak LD First Timer (all coming soon!).
Car-free • Accessibility • Groups • Family • Couples • 50+ • Female Solo • Digital Nomads • Vegetarian • Adventure • Budget • People & Culture • Photography • Relaxation • Slow Travel • Road Trip • Sustainable/Eco • History • Luxury • Outdoors • Wellness
Free
1
Julianne Pineda
Available for hire
Eat, Explore, & Empower: A Journey Through Chicago's BIPOC Businesses
Chicago is filled with a vibrant energy fueled by its diverse BIPOC communities. This guide highlights Black, Indigenous, and People of Color-owned businesses, from delectable cuisine to bookstores and boutiques. Discover Chicago through a different lens that celebrates community.
Couples • LGBTQ+ • Coffee • Foodie • People & Culture • Shopping • Slow Travel
Free
0
My quick take on every restaurant/cafe/bar/bakery I visit this year, updated as I go (plus a score for El Prez). NYC and beyond.
Tip/tricks/suggestions provided for all types of situations (e.g., reservation requirements, best order options, pics of food I ordered, etc.). Newest reviews at the top of the list.
PRO TIP: If you want to search for good reviews, just cmnd/ctrl + F for "8." or "9."
Foodie
Free
0
This is part two of a three-part series regarding Amtrak’s Long Distance Trains. If you are completely new to the idea or are looking for the following trains: Sunset Limited, Southwest Chief, California Zephyr, Empire Builder or Coast Starlight, check out part one (linked below)!
Part two will include the Crescent, Texas Eagle, Capitol Limited, Lake Shore Limited and Cardinal routes.
Car-free • Accessibility • Backpacker • Family • Groups • Female Solo • Vegetarian • Adventure • Budget • History • Outdoors • Luxury • People & Culture • Photography • Relaxation • Road Trip • Slow Travel • Sustainable/Eco • Wellness
Free
0
Every detail about how I pulled off a trip around the Western United States and saw some of the country's most incredible natural wonders for less than $1,300 total. 🤯 Of course, this is the exact route that we used, but there are plenty of other options to choose from. Keep in mind, this is definitely not the itinerary to follow if you are looking to spend a significant amount of time in one specific area. We intentionally planned to see some major highlights along the trip and knew going into it that we would miss a lot of what these parks have to offer.
Adventure • Budget • Outdoors • Photography
Free
4
Nikki | Weekend Postcards
Available for hire
A Guide to Climbing Gyms across the U.S., Canada, Mexico & France
A guide to a variety of climbing gyms located across the U.S. separated by state and Canada, Mexico and France. Activities range from bouldering, top rope, lead and much more! Day passes are available at each location, often include their daily classes and access to their workout gym space. Additionally, some climbing gyms offer additional discounts for students, military members, seniors and early morning climbs. Be sure to check out each locations website to see what each gym offers to maximize your experience.
This is by no means an all extensive list of climbing gyms across the U.S., Canada, Mexico and France but ones I have personally visited while working in various states, cities and countries.
Do you have a favorite climbing gym we should put on our list to check out? Let us know!
Groups • Couples • Family • Digital Nomads • Female Solo • Adventure • Relaxation
Free
2
Welcome to my completely unorganized but oh-so-helpful map of Chicago! An absolute smorgasbord of my own travels and research, suggestions from friends and strangers, and many treasures found along the way, this is where I compile all things Chicago for my future trips and yours. Things I particularly love that you’ll find a lot of:
☕️ Coffee shops & bakeries
🌮 Local cuisine
🏛️ Museums of all kinds
🌳 Gardens & parks
🛏️ Boutique hotels
🍕 Small regional chains with good reputations
All my guides in this category are $5 per 100 places included, but since I add to these constantly, you can lock down the lowest price today and gain a lifetime access!
Family • Couples • Architecture • Art • Budget • Coffee • Foodie • History • People & Culture
$15.00
2
Try ThatchGPT