Results for Chicago
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
Welcome to the after-hours world of Chicago! 🪩
Where the city truly comes alive under the dazzling lights of the night sky and cityscape. Whether you're in the mood for sultry jazz bars, thumping dance floors, speakeasies, or rooftop lounges with breathtaking views, Chicago's nightlife scene has something to enthrall everyone. Get ready to experience the pulse of the city after dark! 🍾
This guide includes:
25+ rooftop bars🍹
15+ nightclubs 🥂
10+ jazz bars 🎷
15+ speakeasies🍷
15+ dive bars 🍻
With this guide, you have the freedom to curate your ideal night out, choosing the experiences that captivate you the most. Craft your own unforgettable and tailor-made journey through Chicago's electrifying nightlife!! 📸
Don’t hesitate to send me an email with any questions, recommendations, and/or feedback. Enjoy your night out on the town!! 🪄
$6.00
0
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
When I first moved to Chicago, 5 years ago, I created a list of every restaurant I wanted to try. I'd add restaurants as they popped up around the city or friends recommended them, and check them off after I went.
I've always loved food, trying various restaurants, and documenting my meal with photographs and videos but when I started planning events for work I got vastly more into keeping up with new restaurants and sharing recommendations. My knowledge of the Chicago restaurant scene increased tenfold.
Here's my tried and true list of favorite restaurants all over Chicago broken down by cuisine: American, Asian, Breakfast/ Brunch, Dessert, Italian, Latin/Spanish/Mediterranean, Markets, Pizza, Rooftops, Seafood & Steak.
Foodie
Free
9
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
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