If you’re planning to spend a weekend in Chicago, then you’ve come to the right place!
Chicago is the biggest city in Illinois and it’s easily one of the most vibrant cities in the Midwest too!
Planning your trip to Chicago last minute?
Make sure to book ahead. Hotels and tours often sell out the closer you get to your trip. Here are our top pics for Chicago!
Top Experiences And Tours In Chicago:
- Chicago River Architecture Cruise (Skip the Ticket Office!)
- Willis TowerSkydeck & The Ledge Ticket (Elevator express entry!)
- Navy Pier Centennial Wheel Ticket (Panoramic views of Chicago!)
- Big Bus Hop on Hop Off Sightseeing Tours (24, 48, or 72-hour options available.)
Hop Hotels In Chicago:
You can explore Chicago in a few days, but I suggest planning a fun weekend trip to Chicago if you have the time!
On this Chicago itinerary, I’ve made sure to include all of the top sites in Chicago as well as a few more unique activities.
Each of these 3 days in Chicago is packed with fun things to do in Chicago that you won’t want to miss.
Plan to spend all day, into the night, exploring! Chicago, like New York City, is a city that never really sleeps.
That means you’ll find things to do well into the night in Chicago, and they’re definitely worth the late bedtime.
I’ve also made sure to include my favorite tips on how to plan a trip to Chicago, like the CityPass.
If you plan to visit a lot of the museums or popular attractions in Chicago that require tickets, you may want to consider getting a Chicago City Pass!
At the end of this Chicago itinerary, you’ll feel prepared to plan the ultimate weekend in Chicago.
So, let’s take a look at my Chicago tips and itinerary for Chicago to help you have a fun weekend trip to Chicago!
Getting To Chicago
It’s really easy to get to Chicago from pretty much anywhere.
If you’re planning to fly into the city, you’ll want to use Chicago Midway International Airport.
Because it’s an international airport, there are direct flights from all over the country.
You can also fly right into the city if you’re traveling from around the world too.
For those who are planning to drive to Chicago, you can do that too.
This is an especially good option if you are planning to extend your trip to explore some of the best day trips from Chicago.
Chicago is easily reached from several highways, so you’ll be able to get there by car or bus.
The city also has several train stations if you prefer to travel by rail.
Getting Around During Your Chicago Weekend Getaway
Chicago’s streets are organized by a grid system, similar to New York City.
So, it’s really easy to get around the city and not get lost.
It’s also a very walkable city, and on this itinerary for Chicago, you’ll be able to walk to just about every stop. However, if you don’t want to walk the enter weekend in Chicago, don’t worry.
Chicago has a great public transit system that includes buses, the subway, and taxis. In fact, it’s the second largest public transportation system in the US.
You can also use ride-share programs or rent bikes to ride around the city. Or you can get tickets for the Hop-On Hop-Off Bus in Chicago.
There’s even a water taxi that you can ride to get around the city!
No matter how you choose to travel around, you’ll find it’s very easy to explore Chicago.
Book Your Hop-On Hop-Off Bus Tickets Here: Getyourguide.com
The Ultimate 3-Day Weekend In Chicago Itinerary
Day 1: Iconic Chicago
For the first day of your 3 days in Chicago, I suggest seeing some of the most iconic sites in Chicago.
You’ll see some of the oldest buildings and areas in the city along with some newer Chicago icons.
This first day is very walkable although most of the walks are about 20-minutes long.
But, you’ll only need to drive or get public transportation towards the very end of the day.
Stop 1: Window Shop At Chicago’s Magnificent Mile
Start your day with a walk around the Magnificent Mile.
The Magnificent Mile is the nickname that’s been given to the northern end of Michigan Avenue.
That’s because it’s full to the brim with luxury shops, restaurants, and boutiques.
Even if you can’t afford to purchase anything from some of these stores, it’s still a really cool thing to do during your Chicago weekend trip.
The area is pretty iconic and it’s one of the things most people want to at least experience during their first time in Chicago.
But even if it’s your twentieth time in Chicago, it’s still fun to walk along the Magnificent Mile.
The front of the shops and restaurants are always elaborately decorated, especially if you’re visiting Chicago during Christmas!
It’s also where you’ll find some of the tallest skyscrapers in the city.
Book Your Chicago Loop Tour Here: Magnificent Mile.
Stop 2: The Navy Pier Is A Must-See Attraction During A Weekend In Chicago
After exploring the Magnificent Mile, you’ll walk about 20-minutes to your next destination, which is the Navy Pier.
The Navy Pier is a huge pier located on the shoreline of Lake Michigan.
There, you’ll find even more things to do in Chicago in a weekend.
The pier has shops, restaurants, and amusement park-style rides.
You can see the city and the lake from the top of the Centennial Ferris Wheel, or spend some time playing games in the pier’s arcade.
During summer nights in Chicago, the Navy Pier has a fireworks show every Wednesday night.
The Navy Pier is a ton of fun during the day, but if you want to see it at night, it’s great too.
Book Here: Centennial Ferris Wheel
Stop 3: Enjoy Beautiful Views Of The City On The Chicago Riverwalk
Next, you’ll head to the Chicago Riverwalk for a walk.
The general starting point of the Chicago Riverwalk is about a 20-minute walk away from the Navy Pier.
However, there are several different entrances to the Riverwalk along the path that you can use to access it.
The Chicago Riverwalk is a pedestrian path that is right alongside the Chicago River.
While you walk, you’ll be able to get some incredible views of the city.
There are also restaurants, small shops, and areas where you can just sit and enjoy the view.
So, if you need a break from walking, you’ll find plenty of spots to rest at this stop on this Chicago itinerary.
Book Your Tickets: Self-Guided Riverwalk Tour
Stop 4: Learn More About Chicago’s History At The Chicago Cultural Center
After spending some time on the Chicago Riverwalk, head to the next stop on this itinerary for Chicago in a weekend.
Your next stop is The Chicago Cultural Center and it’s just over 15-minutes away from parts of the Riverwalk.
The Chicago Cultural Center originally opened in 1897 as the central library building.
Today, it’s where the Mayor of Chicago welcomes visitors like the President of the United States and foreign dignitaries.
When the Mayor isn’t greeting guests, the space is used to house a revolving schedule of unique exhibits.
You can also take tours to learn more about the history of the building itself and its incredible architecture.
It’s open daily from 10 am to 5 pm, so it’s the perfect last stop before you find somewhere to have dinner.
Book Your Tickets: Gilded Age Architecture Walking Tour
Stop 5: Take A Break From Walking While You Enjoy The Open-Top Panoramic Bus Night Tour
After dinner, you’re probably going to want to take a break from all the walking you’ve done on your first of 3 days in Chicago.
However, there are still tons of fun things to do in Chicago in a weekend.
So, I suggest taking one of the Open-top Panoramic Bus night tours.
These buses are completely open on the top level, so on a beautiful night, it’s a great activity.
As you ride around on the bus, you’ll have an expert guide telling you about the different historic buildings you’ll pass.
It’s also a great way to see the city all lit up at night.
While you rest your feet, you’ll get a great tour of the city, and even learn something new.
Book Your Tickets: Panoramic Night Bus Tour
Stop 6: End The Night With Drinks And Live Music At The Green Mill During Your First Of 3 Days In Chicago
Now that you’re rested up a bit, head to your last stop of the night.
For this last stop, you’ll most likely need to take public transportation or get a ride to reach it.
However, it’s totally worth it.
The Green Mill is an iconic jazz bar in Chicago and it’s one of the best things to do in Chicago at night.
If it’s your first time in Chicago, you’ll definitely want to make a trip out to The Green Mill.
They play live music daily, and they also have a full bar.
One thing to keep in mind though is that The Green Mill is strictly cash only. So make sure you stop by the ATM before you get there.
Book Tickets Here: Chicago Food Tour
Day 2: Explore The Heart Of Chicago
For day 2 of your 3 days in Chicago, you’ll be staying in the heart of the city.
Everything on this day of the itinerary for Chicago is really close to each other.
In fact, some of the stops are less than a 10-minute walk away.
You won’t need a car or public transportation at all to enjoy your second day during your weekend in Chicago.
There are so many things to do in Chicago, so let’s get going!!
Stop 1: Explore Millennium Park
Start your second day during your weekend in Chicago exploring Millennium Park.
Millennium Park is probably one of the most popular, if not the most popular, attractions in Chicago.
Each year, the park sees an average of 25 million visitors.
Part of that is because the park is beautiful and because most of the things to do within the massive park are free.
It’s an absolutely massive park that is over 24 acres total and it’s full of a variety of attractions.
In fact, you’ll spend most of day 2 just exploring the different attractions in Millennium Park and the attached Grant Park.
So, that’s where you’ll start the day, to give yourself plenty of time to explore.
Most of the heart of downtown Chicago is situated around Millennium Park.
This makes it easy to exit the park and find a great restaurant or shop and then go back in to explore again.
Book Your Tickets: Millenium Park Self-Guided Tour
Stop 2: See Cloud Gate, Or ‘The Bean’
You probably know about ‘The Bean’, a pretty popular sculpture in Millennium Park.
While it’s known as ‘The Bean’, the sculpture’s actual name is Cloud Gate.
When you get to Millennium Park, after exploring the entrance area of the beautiful park, I suggest heading to Cloud Gate.
Cloud Gate can be found just 400 feet away from the entrance to Millennium Park.
So, you really can’t miss it and if it’s your first time in Chicago, you’ll definitely want to stop by for a picture.
After you get your pictures and admire Cloud Gate, head to your next stop on this itinerary in Chicago.
Book Tickets: Self-Guided Millennium Park Tour
Stop 3: Admire The Artwork At The The Art Institute Of Chicago
Just a short walk away from Cloud Gate, and just outside of Millennium Park is the Art Institute of Chicago.
The Art Institute of Chicago is one of the best things to do during a weekend getaway in Chicago, especially if you’re an art lover.
It’s been voted ‘Downtown Chicago’s #1 Museum’ for a reason!
The museum is open Friday through Monday, from 11 am to 5 pm, and on Thursdays from 11 am to 8 pm.
You’ll need to purchase entrance tickets in advance, and for non-Chicago residents, they are $25 per adult.
Inside the museum, you’ll find artworks by famous artists like Cezzane, van Gogh, Joan Mitchell, Picasso, Monet, Renoir, and de Kooning.
The bulk of their collection is art pieces from Impressionist, Modernist, and Post-Modernist art movements.
However, they also have an extensive collection of historic world art from Mexico, Japan, Egypt, and India.
Make sure to plan to spend plenty of time exploring this amazing Chicago itinerary stop.
Book Tickets Here: Art Institute of Chicago
Stop 4: See The Light Show At The Buckingham Fountain
From the Art Institute, take a short 10-minute walk to Grant Park and the Buckingham Fountain.
The Buckingham Fountain puts on a water show daily, from 9 am to 11 pm, from May to October.
You can catch the show every hour, and it lasts about 20 minutes.
At dusk, the water show turns into a water and light show.
You can see the light show all throughout the night. The last light show starts at 10:35 pm.
That means you have plenty of time to make it to this stop.
You can head to the Buckingham Fountain before dinner, but it also makes for a great after-dinner activity.
Especially if you want to catch the light show too.
Book Tickets: Chicago Night Tour
Stop 5: Go On A Walking Gangsters And Ghosts Tour During Your Weekend In Chicago
A great way to end the second day of your 3 days in Chicago is with a gangsters and ghost tour.
Chicago has a unique history, thanks to the gangsters and bootleggers that called the city home in the early 20th century.
If you want to learn more about this history and look for ghosts at the same time, then this is a super fun weekend trip to Chicago activity.
There are a variety of companies that offer ghost tours throughout the city.
Most of them are walking tours, but there are a few companies that have bus tours as well.
You’ll walk the historic city loop, and based on historical details, learn all about the seedy Chicago underbelly and the ghosts that now haunt the city.
It’s a fun way to end the day and you’ll learn some really cool historical facts too!
Book Tickets: Gangsters and Ghosts Tour
Day 3: Explore The Chicago Skies And The City’s Science Museums
For your last day in Chicago, you’ll be exploring the Chicago skies and some of the best science attractions in the city.
While you can walk to most of these attractions, I suggest using Chicago’s massive public transit system to get around for your last day of 3 days in Chicago.
Plus, your feet are probably pretty tired from your first two days!
Stop 1: See The Views From The Skydeck Chicago And The Willis Tower
Start the last day of your weekend getaway in Chicago at the Skydeck Chicago and Willis Tower.
The Willis Tower was originally known as the Sears Tower, until 2009 when it was renamed.
What makes the Willis Tower so cool is that it’s one of the tallest buildings in the world and it’s the second-tallest building in the US.
It is 1,450 feet high and is 110 stories. At the top of the Willis Tower is the Skydeck Chicago.
The Skydeck Chicago has 360-degree views of the city and a clear skybox that you can walk out onto.
You’ll be able to see the ground below you through the clear floor as well as the full city skyline.
It’s a really cool activity when you’re visiting Chicago for a weekend.
Book Here: Willis Tower Skydeck & The Ledge Tickets
Stop 2: Learn About Space At The Adler Planetarium
From Willis Tower, head to the Adler Planetarium.
The Adler Planetarium is a 45-minute walk away, so you’ll probably want to use public transit to get there.
It is a public museum that is open daily from 9 am to 4 pm. However, on Wednesday, the museum is open late until 10 pm.
Entry to the museum is $19 per adult and includes a wide variety of exhibitions.
You can also choose to add planetarium shows to your ticket, for an additional fee.
Exhibits include images of the Chicago night sky, artifacts from the moon landing and the Mar’s Rover, and tons more.
You’ll want to give yourself plenty of time exploring the Adler Planetarium before you head to your next stop on this Chicago itinerary.
Book Tickets: Eastside Chicago City Exploration Game
Stop 3: Explore The Field Museum Of Natural History
The Field Museum of Natural History is just a short 10-minute walk away from the Adler Planetarium.
It’s a natural history museum, and is actually one of the biggest natural history museums in the world!
For adults, general admission to this cool Chicago museum starts at $29.
You can also add tickets to the various shows and special exhibits the museum hosts as well.
The Field Museum is open daily from 9 am to 4 pm.
Included in the general admission ticket are several unique exhibits.
You can see the Granger Hall of Gems, step inside the Pawnee Earth Lodge, or meet Sue the T-Rex!
Outside of the museum, there is also a large native plant garden that you can stroll through.
Before you head to the next Chicago itinerary stop, you may want to grab a bite to eat. There are food carts near the museum and some great restaurants nearby too.
Tickets Here: Field Museum Of Natural History
Stop 4: Visit The Chicago Museum Of Science And Industry
After you are done exploring the Field Museum, head to the Chicago Museum of Science and Industry.
You’ll want to take public transit to get to The Chicago Museum of Science and Industry from the Field Museum.
The museum is open daily from 9:30 am to 5:30 pm and tickets for adults are $21.95 each.
If you want to see some of the special exhibits, you’ll need to add a ticket to the general admission ticket. But they are always very cool and definitely worth the extra cost.
The exhibits that are included with general admission are super cool too, so you don’t have to see any of the special exhibits to enjoy the museum.
While you’re there, you can explore a German U-boat submarine, learn about tornadoes and avalanches, or step into a fairy castle.
You’ll want to give yourself plenty of time to explore this fun museum on your last of 3 days in Chicago.
Stop 5: Have A Romantic Dinner On A Chicago River Cruise
This next stop on your Chicago itinerary is a great date night in Chicago option if you’re on a couples trip to Chicago.
There are a few different companies that offer romantic sunset dinner cruises on the Chicago River.
As you sail along the river, you’ll get to enjoy a delicious dinner as well as some stunning views of the city skyline.
Some of the cruises also include live music and drinks along with dinner.
If you choose a cruise that doesn’t, don’t worry. Your last stop during your weekend in Chicago includes drinks and stunning views!
Tickets Here: Romantic Sunset Cruise
Stop 6: Drinks At A Rooftop Bar
Your weekend in Chicago is coming to an end, and what better way to end a weekend getaway in Chicago than with drinks on a rooftop bar?
There are several rooftop bars scattered around the city.
Many of them are on hotel rooftops, but there are some independently owned rooftop bars in Chicago as well.
As you enjoy a beverage and look out at the Chicago skyline all lit up at night, you’ll be able to enjoy live music or play games like cornhole.
It just depends on what kind of atmosphere you prefer.
But one thing is for certain, it’s an excellent way to wrap up your trip to Chicago in a weekend!
Where To Stay For A Weekend In Chicago
Acme Hotel Company Chicago
One of the coolest hotels in Chicago is the Acme Hotel Company Chicago.
It’s a boutique hotel located in the heart of Chicago’s River North Neighborhood.
You’ll be just two blocks away from all the excellent shopping and restaurants on the Magnificent Mile.
Each of the rooms is uniquely decorated and many of them have views of the city.
They have a variety of room styles, including rooms with one queen-sized bed or one king-sized bed.
Their suites have two-queen-sized beds or a king-sized bed and come with views of the city and a larger floor plan.
The hotel also has a cocktail lounge, gym, and custom-brewed coffee room delivery services available.
Check Rates Here: Acme Hotel Company Chicago
Another great hotel in Chicago is the Hotel Felix.
The Hotel Felix is also in the River North neighborhood and is just a 14-minute walk from the beach.
It’s also just a quick walk away from Chicago’s Magnificent Mile.
The rooms are decorated in neutral tones, which makes it a very calming space to come back to after a day spent exploring the city.
They offer rooms with one queen-sized bed, one king-sized bed, or two queen-sized beds.
The hotel doesn’t have any dining options on-site, but it is very close to plenty of great restaurants in Chicago.
Check Rates Here: Hotel Felix
The Buckingham Hotel
You’ll find The Buckingham Hotel in the heart of Chicago’s Financial District.
In fact, it’s actually located on the 40th floor of the Chicago Stock Exchange building.
This luxurious hotel in Chicago includes access to an indoor pool, hot tub, and a fitness center within the Buckingham Athletic Club.
When you stay at The Buckingham Hotel, you’ll be just a 5-minute walk away from the Willis Tower and the luxury shops on State Street.
Plus, Grant Park and the Art Institute of Chicago are within a mile of the hotel.
They have a few different room options to choose from.
There are rooms with a king-sized bed or queen-sized bed that have views of the lake and deluxe double rooms, which have two full-sized beds.
They also have a beautiful one-bedroom suite with views of the city, a king-sized bed, a sitting area, and a small kitchenette.
Check Rates Here: The Buckingham Hotel
Where to Eat During Your 3 Days In Chicago
Enjoy Breakfast At Batter & Berries In Lincoln Park
One of the best places for breakfast in Chicago is Batter & Berries.
You’ll find Batter & Berries in Lincoln Park, which makes it a pretty convenient stop first thing in the morning.
The restaurant is probably best known for its ‘French Toast Flights’.
On the menu, you’ll find a wide variety of different French Toast concoctions for you to try.
Along with their French Toast, they also serve breakfast classics like breakfast sandwiches, omelets, and sausage biscuits and gravy.
Batter & Berries can get pretty busy, so if you plan on starting your day there, you might want to try and get there early.
Grab A Beer And A Meal At Revolution Brewing
Revolution Brewing is a really cool Chicago brewery and is actually the largest craft brewery in Illinois.
It’s independently owned and there are actually two locations in Chicago.
At the original location on Milwaukee Street, you’ll find the brewpub and restaurant.
You can stop by Wednesday through Monday for lunch and dinner.
On their menu, they have dishes like cheese curds, a large selection of burgers and sandwiches, and apple-wood smoked wings.
It’s very much a pub-style menu, but everything is delicious and perfectly pairs with the many brews they have on tap.
The Purple Pig Restaurant
One of the most highly rated restaurants in Chicago is The Purple Pig Restaurant.
With over 5,000 reviews on Google, where most of them are at least 4-stars, it’s clear this is a restaurant in Chicago you should visit.
The Purple Pig Restaurant is a fine dining experience located on Michigan Avenue.
Since opening in 2009, The Purple Pig Restaurant has been recognized for its excellence in some of the most prominent food publications. It’s even been Michelin recognized 8 years in a row.
The Purple Pig Restaurant is open daily for lunch and dinner, and reservations are highly suggested.
On their exquisite menu, you’ll find dishes like tuna tartare, salt-roasted beets, squid ink chittara, beef short ribs, and pan-seared Atlantic salmon.
The menu is pretty extensive and there is an entire section of just vegetarian dishes.
So there’s something for just about everyone to enjoy at The Purple Pig Restaurant.
Here are great tips on how to pack light on your next trip using only a carry-on!
There are so many great things to do and see during a weekend in Chicago! It makes for the perfect Midwest weekend getaway.
I hope you’ve found my Chicago tips helpful and now feel ready to plan your weekend getaway in Chicago.
Chicago is an amazing city that has something to interest everyone when you’re exploring Chicago in a weekend.
If you use this weekend guide to Chicago to plan your trip, I’d love to hear about your favorite parts in the comments!