A 2 Day Chicago Itinerary – The Ultimate Guide (2025)
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Are you wondering how to see the best of Chicago in 2 days?
You know I love me a good city visit, and Chicago is at the top of my favorites list!
Chicago is a perfect town for a romantic long weekned, a fun girlfriends’ trip, or a holiday or summer family vacay.
You can easily spend two days in Chicago and see a ton, but I know it will leave you wanting more. So, go back again and again! I have many times!
Follow this perfect 2 day Chicago Itinerary for a great trip that will give you all the highlights.
Is visiting Chicago worth it?
Oh Ya!
Chicago is a city rich in history, culture, incredible architecture, and amazing food! There is so much to see that I highly recommend you spend at least two days in Chicago.
This midwestern marvel offers a buzz that’s different from other American cities. The exquisite skyline along the lakefront and river, makes for a spectacular combination of beautiful nature and superb human engineering.
Here are the top 9 activities to fill your
2 Day Chicago Itinerary
#1 Visit the Chicago Art Institute
I often tell people that this is one of my most favorite museums in the world, becasue it’s a beautiful building and the layout is not overwhelming.
My first visit was with my parents at a very young age and I make sure to return every time I’m in Chicago.
Don’t miss Wood’s American Gothic, Seurat’s A Sunday on Le Grand Jatte, and Hopper’s Nighthawks. And go to the miniature wing!!! They are tiny little rooms, but they are mighty!
Get Tickets in advance!
Go online, book your tickets, and decide if you want to see the special exhibits or not. There’s an infinite amount of art to see in the permanent collection, so don’t feel like you have to spend extra on a special exhibit unless it speaks to you and your crowd!
Tickets are $19 for teens, students, and seniors and $25 for adults. Illinois residents can visit for free on Thursdays.
#2 Walk the Lakefront Trail
The iconic and scenic Lakefront Trail along the east edge of Lake Michigan is the prize of Chicago’s Park District.
The entire trail is 18 miles and begins 9.5 miles south of downtown and continues to the north end at 71st Street.
The trail is populated by runners, walkers, bikes, strollers, rollers, dogs, you name it!
You’ll pass beaches, art, architecture, and incredible views.
I’m always amazed at the size of the lake!
#3 Take a Chicago River
Architecture Tour
This is my biggest must do of Chicago. I really don’t want you to miss it! I’ve done the tour twice and will make sure it’s a habit when visiting Chicago.
The river boat tours offer an insight into the 130 year old history of Chicago, its culture, and its architecture. You’ve never seen such remarkable buildings, old and new, while relaxing in an open air boat and sipping a beverage.
Get Tickets in advance!
I highly recommend Wendella Tours and Cruises 90 minute tour, adults $40, children $18.
Be sure to plan ahead and get tickets online so you’re guaranteed a spot at a time you want.
#4 Hang out at The Chicago Bean
(The Cloud Gate Sculpture)
Artist Anish Kapoor won a design competition in the early 2000’s and his sculpture remains one of Chicago’s most popular sites.
It’s officially named Cloud Gate and was inspired by liquid mercury. However, it’s nicknamed The Bean for obvious reasons.
Made from 168 stainless steel plates, welded together, the seamless Bean offers super fun reflections and distortions and photo ops!
And, it’s right in the middle of AT&T Plaza in Millennium Park along the famous Chicago Loop.
#5 Visit Millennium Park
Millennium Park offers a lot to see and do as you stroll through its 24.5 acres along Lake Michigan. This park is a top midwestern tourist attraction.
You can play in the Splash Fountain, see the Bean, go to the Art Institute, hear a concert at the Pritzer Pavillion, dine at a number of restaurants, rock climb, see gorgeous gardens, and walk on a very cool pedestrian bridge all in one visit!
#6 Enjoy the Chicago Riverwalk
On the south bank of the river, running from Lakeshore Drive to Lake Street, is the 1.25 mile walkway. Like much of Chicago, it offers great views of the river. You can dine, rent kayaks, and take water taxis!
One of my favorite spots are the steps made famous in Ferris Beuller’s Day Off during the Twist and Shout sequence!
#7 Shop on the Magnificent Mile
Yes, it is actually one square mile! Plan a little window shopping.
The luxury shops, hotels, and restaurants along North Michigan Avenue make this area one of the most famous in the world for its old world elegance combined with modern design.
Which are the most famous buildings to see on the Magnificent Mile?
Chicago Water Tower, one of the only buildings to survive the great fire.
The Tribune Tower is the very cool, neo-gothic building which was rebuilt in 1925 after the 1871 fire and is now being made into luxury apartments,
The Wrigley Building (yes, of the chewing gum) is an icon of Chicago for its 1920 construction, made from glazed terra-cotta, combining Spanish and French design unusual angles, a clock that faces many sides, and walkways between its buildings,
The John Hancock is the super tower of Chicago.
#8 Visit the John Hancock Tower –
360 Chicago
A key stop along the Magnificent Mile is the John Hancock Tower, a 100 story skyscraper, which is the fourth highest building in the world.
It’s known for the rooftop bar and observation deck, the 360 Chicago, which offers, yup, you guessed it, 360 degrees of views!
For $8, you can ride The Tilt, a thrill ride which tilts you over the edge of the building from 100 feet above the ground. Not my thing, but go for it and let me know what you think! And you can even take yoga classes up there!
#9 Visit the Willis Tower Skydeck
The Willis Tower formerly known as Sears, is a 108 story building, 110 if you count the penthouse and roof.
Sears held the title of tallest building until 2013. Can you guess which building surpassed it? (a hint, it’s in NYC at One World Trade Center)
The Skydeck Experience at the Willis is a super fun and easy way to get a little history and see 360 degrees of views.
I really recommend this as a great fun-for-the-whole-family kind of activity.
The Ledge glass boxes allow you to step out into the sky of Chicago at 1353 feet above the ground!
The Best Places To Stay In Chicago
→ Best Luxury Hotel – The Penninsula Chicago is considered the best high end hotel. It’s near the beach and all the top sites. Prices start at $825 per night.
→ Best Mid Range Hotel – The London House is my top choice when visiting Chicago becasue of the location, the rooms, and the price. Prices start as low as $343 per night.
→ Best Bargain Hotel – Staypineapple is an iconic hotel on the Loop with free breakfast options and is near all the spots. Prices start at $123 per night.
Chicago Fun Facts
Chicago is the third largest city in the US.
One third of the city was destroyed in the Great Chicago Fire of 1871.
In 1900, engineers figured out how to reverse the flow of the river so it would empty into the Mississippi instead of Lake Michigan!
They actually do dye the river green on St. Patrick’s Day.
Chicago is the site of many a scene from everyone’s favorite movie, Ferris Bueller’s Day Off.
You can see 4 states from the top of the Willis Tower.
Chicago is the home of the Twinkie!
And the site of the first televised presidential debate.
When is the best time to go to Chicago?
Late Spring and early Fall are ideal for the best weather.
Summer can be very hot and humid, and since it is a big walking city, be prepared with lots of water and sunscreen.
Winter and the holiday time are great, if you don’t mind some below freezing temps and extreme wind chill! Chicago has gorgeous holiday displays, plenty of wonter activities, and the lake is always beautiful.
What are the best restaurants in Chicago?
I can’t say enough about how great the food is in Chicago! Chicago is famous for its deep dish pizza and Italian food.
Our personal favorites:
→ Duo Lou Malnati’s Maggiano’s Little Italy
410 N Michigan Ave
Lou Malnati’s Pizzeria is one of THE renowned spots for Chicago deep-dish pizza. The family has a secret recipe for their crust and the restaurant has a cozy atmosphere.
→ Avli River North
702 N Wells St.
Avli River North is one of my most favorite and memorable restaurtants in Chicago. It’s a very classy Greek Restaurant with amazing food and atmosphere. This should be one of your meals, for sure!
→ Quartino
626 N State St.
Quartino’s is a really fun choice for Italian food becasue it is a bustling, family style place where shared plates and a busy atmosphere give you a real taste of Chicago.
Planning Tips for Chicago
~ You won’t need a car in Chicago. Chicago is a great, fly in, fly out city for a long weekend or quick getaway.
~ Walking is the best way to get a feel for the city and ride apps, such as Uber, work great there!
~ Chicago is renowned for its amazing theaters and comedy clubs. keep that in mind when making your plans.
You’re all set to plan a trip to see
the best of Chicago on a 2 day itinerary!
In a nutshell…
This 2 day Chicago itinerary promises to give you a great time. We were able to do all these things, and more on our 2 day trip.
From the architectural marvels along the river to the artistic treasures of the Art Institute, Chicago has a little of something for everyone.
Whether it’s your first visit or a return trip, this guide will help you capture the essence of why Chicago is an excellent choice for a getaway. Enjoy!
You might also like to visit these cities for fun getaways: New York City, San Francisco, New Orleans
xx,
Carrie
