Results for Chicago Couples
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
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
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
A city where iconic architecture, world-class museums, diverse neighborhoods, and a vibrant culinary scene converge to create a dynamic and unforgettable experience. From the stunning Lake Michigan shoreline to the spirited energy of its communities, Chicago invites you to explore a rich tapestry of history, art, and gastronomy in the heart of the Midwest.
You've got five days to spare? We've got just the places you need to visit!
Family • Couples • Groups • Business • Art • Design • Foodie • People & Culture
$15.00
0
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
3
Read along with me as I tell you exactly how I spent the perfect 12 (ish) hour date night in Chicago with my husband and our two best friends.
Reva, my fire wife and book bestie have recently entered our hockey romance era (didn't know that was actually a thing but here we are). After reading a couple hockey smut novels we found ourselves booking a trip to the windy city to enjoy a Chicago Blackhawks game...since it's valentines day next week we invited our hubbies to join us too ;)
It ended up being the absolute perfect evening beyond fulfilling our hearts' hockey desires. We were led to the last standing prohibition era speakeasy, in the basement of the oldest building in Chicago. We shared a second hand smoke fueled nostalgic visit to one of the mob boss locales as well. Foodie finds on this trip were a solid 10 out of 10! Our hotel was just the right amount of classy yet affordable and we plan to return in the summer to spend time exploring the area on foot here too!
If you enjoy this guide please do me a solid and save it to your faves and share with a friend and leave me a comment below :D
Follow me on instagram for all my real time travel finds www.instagram.com/jesstakethetrip/
This is a living guide - if you save it you will receive future updates including any new places and deeper insights!
Couples • Groups • Foodie • People & Culture • Romantic • Adventure • History
Free
4
Known as the “Mother Road,” this is much more than just a road: it is a symbol, an icon that embodies the adventurous and pioneering spirit of the United States. Route 66 is one of the American myths, a real dream for all those who love road trips. It is a legendary road, created to originally connect the city of Chicago with the beach of Santa Monica, California, crossing 8 states such as Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona and California.
Along the itinerary you will encounter bizarre neon signs, historic drive-in cinemas, unusual diners and motels to sleep in, kitschy petrol pumps and many other characteristic places that will make your crossing a real journey back in time.
If you are planning an on the road along Route 66 this is the guide for you!
In this guide you will find everything you need to best organize your on the road to discover Route 66!
Inside you will find:
🗓️Best Time to visit
🛣️Useful information on Route 66
🏨 Where to stay (from hotels to the most unusual motels)
🏛️What to visit (all the places not to be missed)
☕️cafés
🍽️restaurants, pubs and diner
✨unusual places
📌20 day Itinerary
🎒activities & excursions
And lots of other information and advice that will help you better plan your stay...
Happy reading!👀
50+ • Accessibility • Backpacker • Car-free • Couples • Digital Nomads • Family • Groups • Adventure • Art • Budget • Coffee • Foodie • History • Outdoors • Overlanding • Photography • Relaxation • Road Trip • Van Life
$20.00
1
Welcome to the Windy City, located along the shores of beautiful Lake Michigan. Chicago is a hustling and bustling city full of over 70 unique & charming neighborhoods, amazing food and iconic landmarks. Chicago has so much to offer, there is something for everyone to enjoy.
Fun fact: Chicago is NOT the capital of Illinois, even though it is the most well known city in Illinois (We see you Springfield).
This guide includes everything from popular tourist destinations to local stops by neighborhood and tons of restaurants to try. While this is not an all inclusive list of what to do in Chicago, but its a pretty good way to start with over 150 options and tons of personal favorites! Get ready to plan your weekend of fun in Chicago depending on what neighborhood you're located in. Get ready to put on your walking shoes, as you are sure to get plenty of steps in walking around the city. Immerse yourself in the melting pot of cultures.
If you're searching for a specific day-to-day itinerary for Chicago, set up a call and I will help craft the perfect trip based on your needs. Even if you only have a day (which only would begin to scratch the surface) it is absolutely worth it to make a trip to downtown Chicago.
Car-free • Family • Female Solo • Groups • LGBTQ+ • Couples • Digital Nomads • Business • Plus Size • Art • Coffee • Foodie • People & Culture • Shopping
$5.00
4
Esta es mi guía o intinerario de 3 días en la ciudad de los vientos o mejor conocida como Chicago en español
Espero te guste!
Solo Female • Couples • Groups • Adventure • Architecture • Art • Boutique • Budget • Luxury • Foodie • Shopping • Design • People & Culture • Photography • City • Relaxation
$10.00
0
This four day itinerary provides a unique mix of Chicago's iconic landmarks, cultural experiences, diverse neighborhoods, and culinary delights! Adjustments can be made based on personal preferences and the time of year.
Accessibility • Business • Couples • LGBTQ+ • Groups • Family • Female Solo • Architecture • Adventure • People & Culture • Photography • Foodie • Budget • Road Trip • Shopping • Van Life • Outdoors
Free
4
Welcome to an exhilarating journey through the Windy City! In this 5-day Chicago itinerary, we'll explore the best hotels, restaurants, famous landmarks, off-the-beaten-path experiences, and enchanting Christmas activities that make the city shine during the holiday season. Get ready for a memorable and magical adventure.
Female Solo • Couples • Adventure • Architecture • Art • Foodie • History • Luxury
Free
2
Chicago is a great city - regardless of the season. Yes, even in the winter, there is plenty to do...just bundle up! This guide includes a jam-packed Chicago weekend itinerary meant for the winter. With a good balance of indoor and outdoor activities and sightseeing, you're sure to have a great trip. I've sorted this guide in the order we did things - day by day - for easy use! This is not just a list of ideas, but an actual itinerary. I did the planning and research, so you don't have to! This guide is geared toward adults.
In this guide, you'll find:
-Hotel recommendation
-Restaurants we went to (and notes on whether they take reservations or not)
-Outdoor sightseeing
-Guided tour recommendation
-Interactive Shows (and how to get discounted tickets)
-A dispensary (it's legal in Chicago!)
-Cool photo opps
-Tips and tricks for a smooth experience
-And more!
Everything listed in this guide are things I personally did during a weekend trip to Chicago - so I am speaking from experience and honest reviews. We flew in on a Friday night so that we could kick our itinerary off first thing Saturday morning, and flew out on an early Monday morning flight. There was only a one-hour time difference from our home city, so we didn't really need to adjust to the time difference.
Couples • Groups • Adventure • Architecture • Foodie • History • Shopping • Design • People & Culture • Photography • Romantic • City • Winter
$12.00
0
For the past couple of years, Sarah, my best friend from college, and I have planned a girls trip in the winter months to escape the seasonal depression of Denver and Chicago. It's one of my favorite weekends of the year filled with self-care, shopping, fresh air, and copious cups of tea.
We intentionally plan this weekend to have little to no plan so we can be more present. There's no better place to unwind than along the California Coast. Everything in this guide has been tried and vetted by yours truly!
As always, I'm happy to help you plan a custom itinerary for your trip to Big Sur! Just reach out to me directly (:
Slow Travel • Road Trip • Beach • Relaxation • Nature
Free
10
Guide to the least visited National Park in the continental US (and one of the most magical!)
Total trip time: 3-7 days
Nearest major cities to start from:
- Illinois: Chicago
- Minnesota: Duluth, Minneapolis
- Wisconsin: Green Bay
- Michigan: Marquette
Backpacker • Digital Nomads • Couples • Vegan • Groups • Female Solo • Adventure • Budget • Camping • Outdoors • Road Trip • Sustainable/Eco • Van Life
Free
5
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