Traveling to Chicago can be one of the greatest experiences you will have, but it does require some planning. These are recs for anyone from the first time visitor to the locals.
Sections
4
Free Events
Must Try Restaurants (Local Finds Only)
Tours
Shopping and Other Entertainment
Free Events
You will be amazed at how beautiful Chicago really is. Lake Shore Drive is a very popular street and can be chaotic with traffic when nearby events are happening.
Here’s everything you need to know before you go
Lake Shore Drive (2025) - All You Need to Know BEFORE You Go (with Reviews)
A must see for anyone traveling to Chicago for the first time. Beautiful photo opportunity
Clarence F. Buckingham Memorial Fountain
If you are looking for the infamous “Bean” , heres where you can find it! Tons of activities, events throughout the yr here. If you have children it is an absolute must that you check out Maggie Daley Park
Millennium Park
The only indoor “mall” in downtown Chicago
Water Tower Place
This is the heart of tourism for Chicago… You will find boat tours here, lunch and dinner cruises, different events, shopping, restaurants and more!
Navy Pier
Awesome exhibits, free to get in every day of the year, and it is maintained very well.
Lincoln Park Zoo
Must Try Restaurants (Local Finds Only)
These are my recommendations for the local foods that you can only get in the city and must try every time!!!
If you want to try a REAL chicago hot dog... Start here!
Jim's Original: Welcome
Make sure you try the Rib Tips!!! If you have never had tips, this will blow your mind.
Lem's Bar-B-Q
I will let you be the judge but this is my spot for deep dish pizza
Lou Malnati's Pizzeria
For great soul food… highly recommend
Chicago's Home of Chicken & Waffles | Best Soul food in Illinois | Soul food ...
Keith Lee deemed this the best soul food he had in a very long time
Cleos: Home
Over 500 restaurants participate with preset menus. Meals are typically $30- $60 per person, however it often includes 3 course meals that would easily cost hundreds.
Great time to get out and try some restaurants in the city.
Currently scheduled for January 23rd- February 8th
Chicago Restaurant Week 2026 | Official Guide
There are several locations throughout the city. You can find chicago hot dogs, italian beef sandwiches and more!
It is one of my favorites. I love the chargrilled burgers and the prices are similar to any other fast food restaurant
Portillo's
The seafood does not get any fresher than this!! If you are a shrimp lover then you absolutely have to stop by
Calumet Fisheries
This isnt your average ice cream parlor… The must try item is the rainbow cone. It consists of 5 different flavors :Chocolate, Strawberry, Palmer House (vanilla with cherries/walnuts), Pistachio, and Orange Sherbet.
I promise it will blow your mind
The Original Rainbow Cone
Tours
I would absolutely recommend. There are several versions.. There is a nighttime one that includes the fireworks, there is an early morning one and then a regular throughout the day
Such a beautiful experience and opportunity to see the full skyline
Chicago Architecture River Cruise
Of course you have to visit michigan avenue!!!
Michigan Avenue, Chicago - Book Tickets & Tours
A huge portion of the city is surrounded around Black History
Highly recommend any of the listed tours
Explore Black History & Historic Sites in Chicago
If you are into True Crime.. You will enjoy this tour
Chicago Crime Tours and Experiences - Gangsters, Mobsters and Criminals
Awesome way to get a chance to try all of the chicago staples at one time
Chicago Food & City Tours
Check out the highest point and the amazing view!! Cool photo ops as well
Skydeck Chicago
If you ever wanted to take a bus tour of the city… here is your chance!! amazing and I would definitely recommend for the 1st timers
Chicago Bus Tours
An amazing way to see the city from the sky!
Downtown Chicago, IL
Immersive yourself in the southside of chicago
Learn what TV doesn’t tell you and truly understand the real heart of the city
South Side Tours
True Pizza lovers will find this probably the best ever lol
Finally answer the debate about who has the best pizza.
Hint… Its chicago
Chicago Pizza Tours
Such a beautiful option for a family reunion or just an individual experience
City Cruises – Odyssey Lake Michigan Dinner Cruises
