Planning a Chicago trip? As a native Chicagoan, I've got you covered here with my favorite tips for things to do, see, eat and pack in the Windy City.
Sections
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Where to Stay in Chicago
Fun Things to do in Chicago
Chicago Travel Tips
Where to Stay in Chicago
Ideas for where to stay while visiting Chicago
Visiting Chicago on a budget? Save on accommodations by staying outside of downtown
Top 10 Best Hotels Outside of Chicago Downtown for Your Trip
Find your perfect homebase
Top Hotels in Chicago, IL from $76
Find a luxe stay to call home while you're in town
Top NH Hotels in Chicago, IL - Expedia.com
Fun Things to do in Chicago
Ideas for things to do, see, eat and explore
Locals and tourists alike LOVE this, it's one of my personal favorite things to do here
Chicago River 90-Minute Architecture Tour
Choose Chicago (local tourism board) shares their top recommendations for fun things to do in Chicago
Things to Do in Chicago | Fun Attractions in Chicago
My top recommendations for how to spend a long weekend in Chicago
Chicago 4 Day Itinerary: Best Things to Do, See & Eat
A fun and convenient way to see the city - Big Bus Tours Chicago!
Big Bus Tours Chicago
Chicago is a gorgeous city to bike through, and it's a fun way to see the sights
8 Best Bike Tours in Chicago to Explore Like a Local (2025)
Chicago has one of the best Christmas markets in the country, so if you have the chance to visit take it!
Christkindlmarket Chicago 2024: 5 Tips to know before you go
Chicago is a foodie city if I ever met one, make sure you try all the local faves! A guided tour is a great way to try a little bit of everything while making new friends
THE TOP 10 Chicago Food Tours To Try in 2025
Did you know Chicago has a great farmers' market scene?
5 Best Farmers Markets in Chicago for Fresh and Local Finds
Chicago Travel Tips
What to pack, helpful travel tips and more
Visiting or moving to Chicago in the winter? Brave! Keep your feet toasty warm with these winter boots for women.
Chicago Winter Boots: Top Recommendations from A Local -
My top recommendations and mistakes to avoid for first timers in Chicago
33 BEST Chicago Travel Tips By a Local for First-Timers
What's actually worth bringing home from your Chicago adventures
10 BEST Souvenirs from Chicago to Capture the City’s Spirit
I don't necessarily recommend visiting Chicago in winter, but if you do plan to do so (it's still beautiful, just cold) here are some must know tips
23 Best Tips for How to Survive A Chicago Winter (By a Local)
