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Hi, I'm Georgina! A coffee-loving adventure enthusiast here to share my favorite travel tips with you! My goal is to inspire others to get out and explore this wild planet by camping, hiking, or wandering around a fun new city!

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  • Georgina D'Angelo

Unlocking the Windy City: Your Ultimate Chicago Travel Planner

Updated: Jan 24

The Windy City is an incredible place to plan a city vacation. From museums to international cuisine to architecture tours, there truly is something for everyone to enjoy in Chicago.

Complete Travel Guide Chicago

Eat all the food you can as you explore the city. Go on an architecture tour and learn about some of Chicago's interesting history. Stroll through quieter neighborhoods and enjoy the bustle of downtown.

If you have never been to Chicago you have to add it to your US travel list! Alpacka My Bags is here to show you how to best plan a trip to Chicago so you can truly make the most of your time in this wonderful city.

Chicago Travel Planner

How Much Does a Chicago Trip Cost?

Traveling doesn't have to be expensive, even if your destination isn't the cheapest. Learn more about how much a trip to Chicago costs on average so you can start planning.

Figure out your budget so you can fit everything you want to do into your trip. There is so much to see and do in Chicago, but the best news? You can do a lot of things for free and still have the true Chicago experience!

When to Visit Chicago

There is something great about every season in Chicago, so the best time to visit depends on the type of weather you prefer to travel in. Read on to find out when you should visit Chicago!


Cool temps, a little rainy, and gorgeous flowers blooming everywhere. Spring is the perfect time to visit Chicago and enjoy the most of this city's nature scapes.


With warm temps, sunny days, and bustling streets, summer is the time to enjoy festivals, exploring outside, and eating all the ice cream you can in Chicago.


For cool temps, incredible fall fashion, and beautiful fall foliage, visit the great city of Chicago in fall. The weather is perfect.


With a beautiful winter wonderland scene, Chicago goes all out for the holidays making it a great Christmas or holiday travel destination.

Where to Stay in Chicago

There are tons of hotels and Airbnbs available to rent in Chicago, but we've put together a list of our favorite and the best places to stay in Chicago.

Finding the best accommodation really makes a trip come together. If you have a nice, comfortable place to call home and come back to relax in while traveling, it makes any trip more fun.

Chicago hosts a wide variety of hotels, Airbnbs, and more. Depending on your budget and travel style, browse the best places to stay and book today!

After living in the city for three years and returning as often as we can, we've found the best places to stay in Chicago. Take a look!

What to Wear in Chicago

Packing can be one of the most stressful parts of traveling, especially since it's impossible to know exactly what the weather will be like when you're there. But thankfully Chicago has some pretty predictable seasons.

What to wear in Chicago highly depends on the time of year you are visiting as summers get quite warm, and winters get very cold.

My biggest tip is always to bring a waterproof jacket or small umbrella to Chicago any time of year. It's not the rainiest city, but getting caught in the rain with no jacket or umbrella will make for a drenched explorer.

Another rule I always follow when packing is to add the destination to my weather app so I can watch the trends; is it getting colder? Warmer? Will it possibly be rainy?

Also think about layers when packing for Chicago in winter. It's better to have multiple layers to put on if it's cold and be able to take one or two off when it gets warmer, rather than only having a super thick sweater on and roasting all day in it.

We have a detailed packing guide on what to wear in Chicago. Check it out below!

Where to Eat in Chicago

Chicago has one of the best dining scenes I have ever enjoyed. They know how to do delicious food right in Chicago, and the best part is you can get cuisine from all around the world here.

A total of 1.7 million immigrants call Chicago home, and many of them run their own authentic restaurants. You'll find Colombian, Polish, Nigerian, Vietnamese cuisines, and more in Chicago.

Another staple you won't miss in Chicago is coffee! Here you will find some of the best coffee shops with cozy decor and delicious fresh drinks. Find the best coffee spots in Chicago here.

You definitely won't go hungry in Chicago. So go out of your comfort zone and try something new while exploring the great city of Chicago!

What to Do in Chicago

There is a plethora of things to do in Chicago. From museums to architecture tours, baseball games to Broadway shows. This is what makes Chicago a must-visit US travel destination!

There truly is something for everyone here. Even if you enjoy nature, I've never been to a city that makes such an effort to add so much greenery to the busy streets. There are numerous parks, botanical gardens, "beaches," and more to enjoy in Chicago.

Visiting in the winter? Check out the best holiday activities in Chicago!

Take a look at the best things to do in Chicago and have fun exploring this amazing city!

How to Get Around

Good news! You don't need a car to get around Chicago. Walking is a great option if you don't have to travel too far. But the best and cheapest way to get around quickly is by train and bus in Chicago.

Learn all about getting around Chicago like a local and make the most of your time here

With the ultimate Chicago travel planner, you can now plan an epic trip to the Windy City! When are you planning on going?

Remember to book tours and tickets in advance as they can sell out quickly during busy seasons. Make reservations for restaurants you really want to go to. Pack accordingly for the weather.

And if you have any questions about your Chicago trip, please reach out to us! We love this city so we want to make sure everyone else gets the chance to enjoy it!

You might like to read next...

Chicago Trip Planner | Alpacka My Bags Pinterest Cover


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Planning a vacation can be time-consuming and a little overwhelming. To help smooth this process for you, we've compiled our favorite travel planning resources.

From finding the best flights and hotels to the essentials you need to make the most of your trip, check out the Alpacka My Bags travel resources page.

5 Apps & a Free Planner

Join our newsletter to receive the 5 apps I use to plan a trip, my go-to travel essentials list, and a free travel planner pdf!

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Hi, I'm Georgina, adventure enthusiast and creator of Alpacka My Bags. I'm here for all of your travel and adventure planning needs! 


I've been exploring this beautiful planet since I was a child, so I decided it was time to share my travel tips with others to enjoy. After college, I knew the "traditional career path" was not for me.


I needed to travel and explore what this world has to offer. It sounds cliché but you do only live once. So I made going on adventures a priority, and soon realized that I wanted to share them with others so you can enjoy them too! 

My passion is spreading the travel bug and showing others that travel is attainable and so worth it. From itineraries to camping tips to packing lists, Alpacka My Bags has you covered!

Join me, and often my partner and my dog, as we find exciting adventures and travel recommendations for you! If you've been bit by the travel bug just as I have, I hope you find my tips useful for all of your future travels.

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