Planning a trip to Chicago? Find out how to spend the perfect 3 days in Chicago with this weekend itinerary.
With nearly 55 million visitors in 2017, it’s easy to see why Chicago is becoming a hot spot for domestic and international tourists alike. If you’re visiting for the first time, this Chicago itinerary will show you how to spend the perfect 3 days in Chicago.
Whether you’re celebrating a birthday trip or a romantic trip, there is something for everyone in this Chicago weekend itinerary.
Top 10 things to do in Chicago
According to GetYourGuide, here are the top 10 things to do in Chicago. This can help give you some ideas of what to see and do during your 3 days in Chicago.
- Willis Tower – This is where you’ll find one of Chicago’s most popular attractions, SkyDeck Chicago. Visit for FREE with the Chicago CityPASS.
- Navy Pier – Such a fun place to hang out during the summer months.
- 360 Chicago – One of my favorite places to visit at nighttime to see Chicago from above. Visit for FREE with the Chicago CityPASS.
- Chicago River – Walk along the river or take this popular Architecture Boat Tour.
- Art Institute of Chicago
- Aqua at Lakeshore East
- Lake Michigan
- Field Museum of Natural History – Visit this popular museum for FREE with the Chicago CityPASS.
- Centennial Wheel – Soar to heights of nearly 200 feet over Navy Pier with views of Chicago and Lake Michigan.
- Lincoln Park
Save money with the Chicago CityPASS
Visiting Chicago for the first time can be stressful. It’s a big city and there’s lots of fun things to do in Chicago. This can make it challenging to plan an itinerary and determine which attractions to spend your money on.
They’re also recommended by Expedia and Chicago CityPASS currently has a TrustScore rating of 4.8/5 on Trust Pilot. Many people have already used the Chicago CityPASS (including me) for their Chicago trip and posted happy reviews.
With the Chicago CityPASS, you can save time, money, and enjoy stress-free sightseeing. But don’t just take my word for it. Check out these recent Google reviews.
PRO TIP: Buy the pass online to save time and hassle. To buy the Chicago CityPASS, click here.
What’s included in the Chicago CityPASS?
✓ Visit Chicago’s 5 top attractions
✓ Valid for up to 9 days
✓ Save 48% on regular ticket prices
✓ Mobile or printable pass option
Chicago CityPASS is a multi-attraction sightseeing card where you can choose to visit 5 top attractions all for ONE low price.
This includes free entry to:
- Field Museum (VIP Entry and All-Access Pass)
- Skydeck Chicago (Expedited Entry)
- Shedd Aquarium (Priority Entry)
You’ll also get your choice of the following 2 attractions:
- Art Institute of Chicago (Fast Pass)
- Museum of Science & Industry
- 360 Chicago Observation Deck
- Adler Planetarium
The Chicago CityPASS was SO helpful for our weekend trip. This is the best way to visit Chicago. I didn’t have to worry about dealing with money and waiting in long ticket lines.
Simply show your mobile pass at each attraction to skip the long ticket lines and start your sightseeing adventure. We found the pass was an excellent value for our Chicago itinerary and made visiting attractions stress-free.
How to get your Chicago CityPASS:
Step 1: Head to Chicago CityPASS to purchase your tickets.
When you purchase through GetYourGuide, you can cancel up to 24 hours in advance to receive a full refund. This can give you peace of mind just in case your plans change.
Step 2: You can use your mobile phone or print your voucher. With email, you’ll get instant access to your mobile tickets. Simply present your mobile tickets at each attraction. You can also print your tickets if you prefer a paper copy.
Step 3: Now you have FREE access to any of the top 5 Chicago attractions included in the Chicago CityPASS. You can activate your pass anytime within 12 months from the date of purchase.
Once activated, your pass is valid for 9 consecutive days, so there’s no need to rush through each attraction.
Read Next: The cheapest way to see Chicago attractions
Plan ahead to avoid disappointment
Chicago can be busy during the summer months. If you have your heart set on visiting a certain attraction, seeing a particular show, or eating at a specific restaurant, you should book in advance.
Booking in advance is usually cheaper and saves you the hassle of having to wait in long line-ups when you’re in Chicago. Just skip the line and head straight to the attraction.
Even if you’re using the Chicago CityPASS, you’ll need to book some attractions in advance.
When you purchase the Chicago CityPASS, you can make reservations and book the time slot you wish through their website.
Below are some of the popular attractions and tours that you may want to consider booking in advance.
- Shedd Aquarium (Advance reservations are required)
- Skydeck Chicago (Advance reservations are required)
- Museum of Science and Industry (Advance reservations are required)
- 360 Chicago Observation Deck (Advance reservations are required)
- Field Museum (Advance reservations are NOT required for CityPASS guests. Admission is on a timed-entry basis)
Where is the best part of Chicago to stay in?
After visiting Chicago several times and staying in different neighborhoods, I recommend staying in one of these 5 areas:
- Magnificent Mile – The BEST neighborhood for first-timers
- The Loop – Ideal for all travellers. See Cloud Gate and Millennium Park.
- River North – Ideal for all travellers. See Navy Pier and the Tribune Tower.
- Gold Coast – Ideal for luxury travellers.
- South Loop – Ideal for all travellers, especially museum lovers.
Best Chicago hotels for every budget:
If you’re traveling on a budget, these are the best cheap hotels in Chicago:
- La Quinta by Wyndam Chicago Downtown (Close to Willis Tower / Skydeck)
- Hampton Inn Chicago Downtown/N Loop/Michigan Ave (Close to Cloud Gate)
- Courtyard by Mariott Chicago Downtown/Magnificent Mile (Great for shopping)
If you have some more wiggle room in your budget, below are some of the best mid-range hotels in Chicago:
- Fairfield Inn & Suites Chicago Downtown/River North
- DoubleTree by Hilton Chicago Magnificent Mile
- Springhill Suites Chicago Downtown/River North
If you want to splurge on your accommodations, below are Chicago’s top luxury hotels:
Best way to get around Chicago
For this downtown Chicago itinerary, I recommend using the city’s public transit. Chicago’s public transportation is excellent and will take you to all the attractions on your itinerary.
Once you get to the station, you have 3 options for paying your fare:
- You can buy a Ventura ticket – This is good on CTA (Chicago Transit Authority). You can get a Single Ride Ticket, a 1-Day CTA Ticket (good for unlimited rides for 24 hours), or a 3-Day CTA Ticket (good for unlimited rides for 72 hours.
- You can buy a Ventura Card – This is a rechargable card with money loaded to cover fare for up to seven people. You can get your pass at any Ventura Vending machine or Ventura retailer in Chicago.
- If you have Apple Pay, Android Pay or Samsung Pay set up or have a contactless bankcard – Simply go straight into the gates and touch your card there.
Below are some more great ways to get around the city:
- Walk – Chicago is a big city, but it’s very walkable. Just make sure to wear comfortable shoes – this is a must when visiting Chicago since you’ll be walking around a lot.
- Hop-On Hop-Off bus tour – Yes, this is a bit touristy, but it’s a great way to see the city’s top attractions and learn more about local landmarks.
- Ride the “L” train – This is the elevated public transit train in Chicago. It’s safe, cheap and one of the best ways to get to all the must-see spots on your Chicago itinerary.
- Seway – Taking a seaway tour can be another fun and exciting way to explore the city.
- Cab or Uber – These are expensive, but it’s a convenient way to get around Chicago.
How to get to Chicago from the airport
Chicago has two airports you can choose to fly into: O’Hare or Midway International Airport. Both airports offer “L” trains that you can take to and from the airport to downtown.
The “L” train is a safe, cheap, and fast way to travel from the airport to your Chicago accommodations.
- From O’Hare: The Blue Line “L” train will take you from O’Hare to downtown in about 45 minutes. It costs around $5.00.
- From Midway International Airport: The Orange Line “L” train will take you from Midway International Airport to downtown in about 25 minutes. It costs around $2.50.
- Chicago CityPASS review: Is it worth it?
- Quick guide to visiting Chicago on a budget
- Chicago CityPASS vs. Chicago Explorer Pass – Which is better?
- 10 reasons to visit Chicago in the winter
Chicago Itinerary: Day 1
Highlights of Day One in Chicago:
Arrive at Skydeck Chicago before it opens. This way you’ll be one of the first people in line to catch the elevator to the top.
Plan to spend at least one hour at the Skydeck (depending on how busy it is and how long you wish to stay).
Tips for visiting Skydeck Chicago:
- The best time to visit is just after opening or after sunset.
- If you want to catch a view of the sunset, plan to arrive at least 30-60 minutes before sunset time. This allows you to view the city in the daytime, twilight, and nighttime.
- For those planning to take photos towards the windows, make sure to use the “blacklight” function of your camera if it’s an option. Also turn your flash off and polarizer filter for the best photos.
- The Skydeck has implemented timed ticketing. You’ll need to reserve your tickets in advance.
- If you want to skip the long lines, consider getting Expedited Entry tickets. This will save you a ton of time with an express line to the elevators.
- Expedited Entry tickets are included when you purchase the Chicago CityPASS.
Interesting facts about Skydeck Chicago:
- The Willis Tower (formerly known as Sears Tower) is 1,450 feet (443 meters) high. Including the twin antenna, it’s 1,730 feet (520 meters) high.
- The Willis Tower is the 12th tallest building in the world, and the second tallest building in North America and the Western Hemisphere. It’s 110 stories tall.
- The Willis Tower has the highest public veiwing area in the USA.
- The Skydeck is 1,353 feet (412 meters) above the ground.
- One a clear day, you can see four states – Illinois, Indiana, Wisconsin, and Michigan. The visibility from the Skydeck is approximately 40-50 miles (65-80 kilometers).
- The Willis Tower elevators operate as fast as 1,600 feet (488 meters) per minute.
Art Institute of Chicago
From here, take transit or walk over to the Art Institute of Chicago. Plan to spend at least two hours touring the galleries.
The Art Institute of Chicago was named the top museum in the world. It’s also ranked as the #1 attraction in Chicago on TripAdvisor. You definitely don’t want to miss this when planning your Chicago itinerary.
Save time with the Chicago CityPASS
As you can see, getting the Chicago CityPASS is a good option if you want to visit the 5 top-rated attractions, save 48% off the regular ticket price, and maxmize your sightseeing time.
Tips for visiting the Art Institute of Chicago:
- The best time to visit the Art Institute of Chicago is early on a weekday, between noon and 3:00PM.
- Kids under 14 years old can visit the museum for FREE. Chicago teens under 18 years old can also visit for free.
- If you want to skip the long lines, consider getting the Fast Pass. This allows you to bypass the general admission line at entrances AND offers expedited access to ticketed special exhibitions.
- Fast Pass tickets are included when you purchase the Chicago CityPASS.
- If you’re short on time, the must-see things at the Art Institute of Chicago are the collections of Impressionist and Post-Impressionist art, which is considered some of the best in the world.
- The most famous paintings at the Art Institute of Chicago include The Bedroom by Vincent van Gogh, A Sunday Afternoon on the Island of La Grande Jatte by Georges Seurat, Nighthawks by Edward Hopper, American Gothic by Grant Wood, Water Lilies by Claude Monet, and The Child’s Bath by Mary Cassatt.
If you’d prefer to learn about space, I recommend visiting the Adler Planetarium which is America’s first planetarium and a premiere resource for inspiring the next generation of space explorers. This is a fun museum to learn about astronomy and astrophysics.
Tips for visiting the Adler Planetarium:
- This museum is not as busy as the other big museums in Chicago, so there’s no need to get there early to beat the crowds.
- The best time to visit is in the summer months, especially if you want to observe the night sky.
- The Adler Planetarium houses 3 full-size theatres and 2 full-size planetariums.
- If you’re using the Chicago CityPASS, you’ll get FREE access to all of the exhibitions, plus TWO sky shows. Each show is 30-minutes long. Plan to spend at least 2-3 hours exploring Adler Planetarium.
- The Adler Planetarium has Galileo’s Cafe, which offers fresh soups, flatbreads, sandwiches, salads, and desserts to enjoy while taking in a beautiful view of Chicago’s skyline.
Millennium Park + The Loop
Grab lunch at a nearby café and browse the shops in The Loop. Make your way over to Millennium Park to see the famous Cloud Gate (a.ka. the bean). It’s usually busy during the day, but you might get lucky by going early in the morning before other tourists arrive.
Chicago Architecture Boat Cruise
Walk up Michigan Avenue to the Chicago Riverwalk. Chicago’s architecture is full of history which is why many people like to take an architecture boat cruise. This is the most popular tour which takes you on a 60 (or 75 minute) tour to discover hidden architectural gems among the city’s renowned landmarks.
Chicago’s Riverwalk is one of the prettiest aspects about the city and the perfect area to be at sunset as the buildings light up the night.
More fun things to do in Chicago:
- Navy Pier Centennial Wheel
- Chicago: Lake Michigan Gourmet Brunch / Lunch / Dinner Cruise
- Chicago: 90-Minute Mob & Crime Bus Tour
Eat deep dish pizza
Sit down for dinner at one of Chicago’s popular deep dish pizza restaurants (my favorite is Lou Malnati’s). The pizza takes at least 30 minutes to arrive at the table after ordering, so make sure to get a salad or appetizer if you’re hungry.
After dinner, catch transit to Second City to see a show. This theatre specializes in sketch comedy and improv. After opening its doors in 1959, it has become the most influential comedy theatre in the world.
Another popular nighttime activity is to head to Navy Pier to enjoy an up-close of the fireworks with a River Architecture Cruise. Don’t forget to bring your camera!
Prep for your trip to Chicago
Chicago Itinerary: Day 2
Highlights of Day Two in Chicago:
Begin your morning at the Shedd Aquarium. Plan to get here when it opens, as it gets busy (depending on the time of year you decide to visit).
This is the largest indoor aquarium in the world and not to be missed when visiting Chicago. Housing more than 8,000 aquatic animals, you can easily spend two hours (or more) exploring all the exhibits.
Tips for visiting the Shedd Aquarium:
- The best time to visit the Shedd Aqarium is early in the morning on weekdays, especially Wednesdays, Thursdays, Fridays.
- Most visitors spend between 2 and 3.5 hours exploring the Shedd Aquarium.
- If you want to see everything, get the All-Access Admission. This allows you to get into ALL of the exhibits including seasonal Stringray Touch and a 4-D experience. All-Access Admission is included when you purchase the Chicago CityPASS.
- The Shedd Aquarium offers lockers for a small fee. Here you can store your bags and other personal belongings if you want.
After the aquarium, walk over to the Field Museum. This is one of the largest natural history museums in the world and one of my favorite hot spots in Chicago.
Here you can explore over 26 million biological specimens and cultural artifacts and learn about the story of our planet and its cultures. Depending on your interests, plan to spend a couple of hours here.
Tips for visiting the Field Museum:
- The best time to visit the Field Museum is on weekdays or early weekend mornings right when they open. The busiest time to visit is Saturday and Sunday between 11:00AM and 4:00PM. Fortunately the museum is large, so even on busy days, it won’t feel too crowded.
- The museum’s exhibit space is almost half a million square feet! Be sure to wear comfortable shoes and plan to spend at least 3-4 hours exploring the museum.
- If you want to see everything, get the All-Access Pass. This includes entry to all the permanent exhibits and regularly priced ticketed exhibitions, plus your choice of on digital 3D film.
- All-Access Admission is included when you purchase the Chicago CityPASS.
- The best things to see at the Field Museum are Sue the T-Rex, Evolving Planet, Inside Ancient Egypt, Underground Adventure, Grainger Hall of Gems, The Ancient Americas, McDonald’s Prep Lab, and Genghis Khan.
Grant Park, Magnificent Mile, and Navy Pier
If the weather is nice, grab lunch to-go and eat it in Grant Park (just above Museum Campus). This is a nice way to take a break, relax, and enjoy the scenery.
Take transit (or walk) up Michigan Avenue north of the river to shop the Magnificent Mile. If you’re not in the mood for shopping, check out Navy Pier which is a Chicago Landmark and offers a variety of attractions for all ages to enjoy.
Museum of Science and Industry
If you’re interested in learning about science, I recommend visiting Chicago’s Museum of Science and Industry, which is the largest science center in the Western Hemisphere.
Tips for visiting the Museum of Science and Industry:
- The best time to visit MSI is right when it opens on weekdays. Weekends are the busiest, especially during the summer months when school is out.
- MSI has over 400,000 square foot of exhibit space and is the largest science museum in the Western Hemisphere.
- Before visiting, I recommend checking out their website first to look at the experiences, permanent exhibits and tours to think about what you want to see.
- Admission to MSI is included for free when you purchase the Chicago CityPASS. This includes museum entry plus one timed-entry experience (Giant Dome theatre film or Motion Ride).
- The most popular things to see at MSI include Coal Mine (descend into a coal miner’s world to learn about the machinery and mining methods), U-505 Submarine (a 35,000 square foot exhibit that showcases the German submarine that was captured in World War II), Whispering Gallery (where you can whisper to a friend from across the room and they’ll hear it), Baby Chick Hackery (where you can watch real baby chicks hatch out of their shells), Science Storms (where you can step into a control booth of a tornado), Planes, Trains & Automobiles, and Numbers in Nature (where you can check out a mirror maze).
Make your way up Michigan Avenue to visit the top of the 360 Chicago.
Chicago is beautiful at night and I would highly suggest visiting the Skydeck during the day time, and the 360 Chicago at night to make the most of your Chicago itinerary.
Tips for visiting 360 Chicago:
- The best time to visit 360 Chicago is before 10:00AM so you can beat the crowds. Make sure to check the weather beforehand so you can make the most of your experience by visiting on a clear day.
- To check out the sunset, make sure to arrive one hour before sunset time.
- If you’re feeling brave, check out Tilt which literally tilts you outward from the building. This allows you to see the city as if you were floating above it! (There’s an added $8 cost to experience Tilt).
- If you don’t want to pay the extra fee to experience Tilt, consider checking out The Ledge at Skydeck Chicago. It’s free with your Skydeck ticket.
- To save time and skip the long lines, get Express Entry tickets. This is included when you purchase the Chicago CityPASS.
If you’re feeling fancy, enjoy a delicious dinner at the Signature Room on the 95th floor with the best view of the city. Or if you prefer to just stop in for a drink, check out the Signature Lounge and watch the city lights glimmer in the night sky.
More fun things to do in Chicago:
- Chicago: Gangsters and Ghosts 2-Hour Walking Tour
- Chicago Hop-On Hop-Off Bus Tour
- Chicago 1.5-Hour Romantic Sunset Cruise
Chicago Itinerary: Day 3
Highlights of Day Three in Chicago:
Lincoln Park Zoo
Start your morning by visiting the Lincoln Park Zoo which has free admission and is one of the oldest zoos in the USA (opening in 1868). Plan to spend two hours exploring the zoo grounds.
Explore Wicker Park
Hop on transit and head to Wicker Park to browse vintage shops and boutique stores in this trendy Chicago neighborhood. Grab a bite to eat for lunch at one of the many restaurants or cafes in the area.
Shop in the Gold Coast neighborhood
After exploring Wicker Park, take transit to the Gold Coast neighborhood which is nestled just north of downtown Chicago.
This is one of the country’s most affluent neighborhoods filled with historic homes, designer shops and one-of-a-kind boutiques.
If you’re looking to relax, sit down at one of the neighborhood cafes for a coffee or tea before heading down Rush Street towards Michigan Avenue.
A popular thing to do in Chicago is to take a food tour. Chicago has some of the best food in the world, so if you’re a foodie, I highly recommend checking out one of these fun tours:
- Chicago: Lake Michigan Gourmet Brunch, Lunch or Dinner cruise
- Chicago Secret food tour
- Chicago: Bikes, Bites, and Brews biking tour
As your last evening on your vacation, you have a few options to add to your Chicago itinerary.
For theatre lovers, check out a performance at The Chicago Theatre.
If you feel like doing an activity, head to 10pin Bowling Lounge under the Marina Towers north of the Chicago River. They offer a selection of beers and upscale snacks.
Chicago’s nightlife also offers a variety of lounges and bars to relax and unwind with a drink or two.
More fun things to do in Chicago:
- Amazing Lakefront Segway Tour of Chicago
- Chicago: 45-Minute Private Helicopter Flight for 1-3 People
- Chicago Food Tasting: 2.5-Hour Guided Walking Tour
3 days in Chicago FAQs
How many days do you need in Chicago?
3 to 4 days should be enough to see the top attractions in Chicago. However, depending on your interests and travel style, you can certainly spend a week in Chicago exploring the area and main tourist attractions.
Is 3 days in Chicago enough?
3 days is enough to see most of the top attractions in Chicago. If you want to take your time exploring the different neighborhoods, then you may want to consider staying 4 or 5 days in Chicago.
What can you see in Chicago in 3 days?
With this 3-day Chicago itinerary for first-timers, you can check out the city’s most popular attractions over a weekend. This includes the Art Institute of Chicago, Skydeck, 360 Chicago, Field Museum, Shedd Aquarium, Navy Pier, Adler Planetarium, Lincoln Park Zoo, and Museum of Science & Industry.
This itinerary also includes exploring the top neighborhoods in Chicago, including The Loop, Magnificent Mile, Gold Coast, Grant Park, and Wicker Park.
Is 2 days enough for Chicago?
With so many things to do, see and eat in Chicago — it’s impossible to do everything in just 2 days. However, 2 days is enough to see some of the city’s top attractions, such as Skydeck, the Art Institute of Chicago, 360 Chicago, and Navy Pier.
What’s the best time to visit Chicago?
The best time of year to visit Chicago is in the spring (April through May) and in the fall (September through October). This is when the temperatures are warm and comfortable.
Winters in Chicago can be very cold. But if you don’t mind the cold, Chicago is beautiful during the winter months (November through March). You’ll also find cheaper hotels rates.
How can I spend 2 days in Chicago?
If you want to spend 2 days in Chicago, it’s easy to visit all the main tourist attractions and museums. Arrive the evening before, so you can have two full days to explore Chicago or you can arrive early in the morning.
For 2 days in Chicago, I recommend checking out the Shedd Aquarium, Field Museum, Magnificent Mile, 360 Chicago, Skydeck Chicago, Art Institute of Chicago, Millennium Park (Cloud Gate), Chicago’s Riverwalk (Consider taking an Architecture Boat Cruise).
What should I do in Chicago for a week?
Below are the best things to do in Chicago in a week for first-time visitors. You can check out these places for free with the GO City Chicago Pass.
- Hop-On Hop-Off Bus Tour
- Art Institute of Chicago
- 360 Chicago
- Skydeck Chicago (Willis Tower)
- Shoreline Architecture Boat Cruise
- Millennium Park to see Cloud Gate
- Shedd Aquarium
- Field Museum
- Museum of Science and Industry
- Adler Planetarium
- Navy Pier
- Robie House
- Grant Park and Buckingham Fountain
- The Magnificent Mile
- Lincoln Park Zoo
Is Chicago expensive for tourists?
Chicago is slightly more affordable for tourists than other large cities in North America, such as New York City.
You should plan to spend around $221 per day during your vacation to Chicago (per person).
According to BudgetYourTrip, a vacation to Chicago for one week will cost around $1,547 per person. This means a trip for two will usually cost $3,095 for one week.
Is December a good time to visit Chicago?
Yes, this is one of the best times to visit Chicago because it’s the least crowded and hotel prices are low in early December, January and February. My sister and I went to Chicago in mid-December and found it was a great time to see the city decorated for the holidays.
Is Skydeck better than 360 Chicago?
Both observatories are worth visiting if you have the time.
Skydeck Chicago tickets are more expensive than 360 Chicago, but it also includes access to The Ledge for free. At 360 Chicago, you have to pay an extra $8 to check out the Tilt attraction.
Skydeck Chicago’s observatory is higher than 360 Chicago. The Skydeck is on the 103rd floor of the Willis Tower (1,353 feet / 412 meters). 360 Chicago in on the 94th floor of the John Hancock Building (1,000 feet / 305 meters).
Even though Skydeck Chicago’s observatory is slightly higher, it’s hard to tell the difference when you’re at 360 Chicago. Both observatories offer absolutely spectacular views of the city.
The wait times at Skydeck Chicago is twice as long as the wait times at 360 Chicago, especially during peak times. This is because Skydeck Chicago gets more visitors annually than 360 Chicago.
What is Chicago known for?
Chicago is famous for its deep-dish pizza, Chicago-style hot dogs, jazz music, Cloud Gate at Millennium Park, Navy Pier, its skyscrapers, Wrigley Field, Lincoln Park, the Chicago Loop, Garfield Park Conservatory, Chicago Riverwalk, Magnificent Mile, and 1920s gangsters.