The Best of Chicago In 2 Days

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This is my guide for seeing 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! Plan a trip to see the best of Chicago in 2 days and I guarantee you will not be disappointed.

You can easily spend two days in Chicago and see a lot, but I know it will leave you wanting more. So, go back again and again! I have!

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See The Best Of Chicago In 2 Days
See The Best Of Chicago In 2 Days
See The Best Of Chicago In 2 Days

Some fun facts about Chicago:

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.

See The Best Of Chicago In 2 days


Chicago is the home of the Twinkie!

And the site of the first televised presidential debate.


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, and I think you’ll agree that the exquisite skyline along the lakefront and river, makes for a spectacular combination of beautiful nature and superb human engineering.

Know before you go

Best Time To Go

The best times, if you can get away, are late Spring, Summer, and early Fall.

Summer can be very hot and humid, and since it is a big walking city, be prepared with lots of water and sunscreen.

If you enjoy below freezing temps, extreme wind chill, then go in the winter. Chicago has gorgeous holiday displays and the lake is always beautiful.

Where To Stay

I highly recommend the London House on East Wacker Dr. It was affordable on Expedia, very pleasant,  accommodating, and in the absolute best location!

There’s a restaurant on the street level that is perfect for breakfast, but if you want a drink or dinner on the rooftop, make reservations very far in advance!

There are also many vacation rentals in Chicago. Check out VRBO.


I can’t say enough about how great the food is in Chicago! Chicago is famous for its deep dish pizza, and has many excellent restaurants. Some favorites:

Pizzeria Uno
Duo Lou Malnati’s Maggiano’s Little Italy
Avli River North


No need for 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.

See The Best Of Chicago In 2 Days
See The Best Of Chicago In 2 Days
See The Best Of Chicago In 2 Days

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!


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.

See The Best Of Chicago In 2 Days
See The Best Of Chicago In 2 Days

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! 

How To Spend 2 Days In Chicago
See The Best of Chicago In 2 days
See The Best Of Chicago In 2 Days

Chicago River Architecture Tour

This is my biggest must do of Chicago, so 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 have never seen such remarkable buildings, old and new, while relaxing in an open air boat and sipping a beverage.

Get Tickets

 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.

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.

Millennium Park

Millennium Park offers a lot to see and do as you stroll through its 24.5 acres along Lake Michigan. This park has become the top midwestern tourist attraction becasue 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.
See The Best Of Chicago In 2 Days
See The Best Of Chicago In 2 Days
The Chicago Riverwalk


On the south bank of the river, running from Lakeshore Drive to Lake Street, is the 1.25 mile walkway. Again, like much of Chicago, it offers great views of the river and activities, restaurants, chances to rent kayaks on the river (yes, its a thing!) and take water taxis.

One of my favorite spots are the steps made famous in Ferris Beuller during the Twist and Shout sequence!

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.

Beautiful Buildings

Chicago Water Tower, one of the only buildings to survive the great fire,

The very cool, neo-gothic Tribune Tower, 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) 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,

And, of course, the John Hancock super tower.

Maybe you will find that special souvenir along the Magnificent Mile?

See The Best of Chicago in 2 Days
See The Best of Chicago in 2 Days
See The Best of Chicago in 2 Days
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!

And, 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!

Willis Tower Skydeck


The 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 is 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! 

See The Best Of Chicago In 2 Days
See The Best Of Chicago In 2 Days
See The Best Of Chicago In 2 Days
See The Best Of Chicago In 2 Days
See The Best Of Chicago In 2 Days
See The Best Of Chicago In 2 Days


Hi There! I’m Carrie.

Carrie Green-Zinn Bio Page

I’m a native New Englander, turned New Yorker, turned California girl! Following a dance career, working as a dance therapist, and being a school psychologist, I’m now ready to share my passion for photography and travel with you! I absolutely love seeing the world with my family and friends. I know you feel the same! Let’s go! 

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