Last updated June 2020.
With nearly 54.1 million visitors in 2016, 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 itinerary will show you how to spend 3 perfect days in Chicago.
Whether you’re celebrating a birthday trip or a girls weekend, there is something for everyone in this Chicago itinerary.
Saving Money on Sightseeing & Attractions
Visiting Chicago for the first time can be stressful. Chicago is a big city and there’s lots of fun things to do and see. It can be challenging to plan an itinerary and determine which attractions to spend your money on.
They’re also recommended by Expedia and 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 TripAdvisor reviews.
PRO TIP: Buy the pass online to save time and hassle. To buy the Chicago CityPASS, click here to go to the official website.
Here’s what’s included in the Chicago CityPASS:
✓ Visit 5 popular Chicago attractions
✓ Valid for 9 days
✓ Save 50% on regular ticket prices
✓ Mobile or printable pass option
The Chicago CityPASS is a pre-paid booklet of tickets which gives you FREE fast-track entry to the top 5 attractions in the city. This includes:
Standard Entry Price
FREE with the Chicago CityPASS
Standard Entry Price
FREE with the Chicago CityPASS
Standard Entry Price
FREE with the Chicago CityPASS
Plus, you’ll also get free entry two more popular Chicago attractions. You can choose from the follow 4 top sights:
- 360 Chicago* – Express Entry OR Museum of Science and Industry*
- Art Institute of Chicago* – Fast Pass OR Adler Planetarium* – VIP Entry
*Your CityPASS tickets include the option for you to choose between two attractions. There’s no need to decide upfront where you’d like to visit. You can choose when you get there. I chose to visit 360 Chicago and the Art Institute of Chicago.
The Chicago CityPASS was SO helpful for our weekend trip. I didn’t have to worry about dealing with money and tickets. 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 and made visiting attractions stress-free.
Is the Chicago CityPASS worth it? Check out my honest review of the Chicago CityPASS here.
How to get your Chicago CityPASS:
Step 1: Head to the Chicago CityPASS official website to purchase your tickets.
Step 2: Choose between receiving your CityPASS tickets via email or having ticket booklets shipped to you. 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 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.
Still on the fence about the Chicago CityPASS? You may want to consider the Go Chicago Pass instead. This is another great way to save money on sightseeing and tours in the city.
Read Next: The cheapest way to see Chicago attractions
Saving Money on Accommodations
While Chicago’s hotel rates can skyrocket during the summer months, there are plenty of ways to have an incredible trip without breaking the bank. One of my favorite ways to save money on accommodations is to book through Airbnb.
I have used Airbnb throughout North America and have always had a good experience. (I booked an Airbnb for my upcoming trip to Chicago in June 2018). It’s great for groups, friends, or couples since prices are often cheaper than hotels.
Getting Around the City
For this downtown Chicago itinerary, I recommend getting a CTA metro pass. You can get your pass at any Ventura Vending machine or Ventura retailer in Chicago. It’s also a good idea to wear comfortable shoes — this is a must when visiting Chicago since you’ll be walking around a lot.
- Chicago CityPASS review 2019: Is it worth it?
- Quick guide to visiting Chicago on a budget
- 10 reasons to visit Chicago in the winter
Arrive at Skydeck Chicago before it opens. (9:00am during the summer and 10:00am during the winter months). 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).
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 as part of Chicago CityPASS. It’s also ranked as the #1 attraction in Chicago on TripAdvisor.
PRO TIP: Having the Chicago CityPASS can save you a lot of time when sightseeing. When I was visiting Chicago in the summer, there was a huge line up to get into the Art Institute of Chicago. If you buy the CityPASS, you can skip the long lines and walk straight inside the museum. You’ll feel like a VIP with your CityPASS!
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.
Free admission to Skydeck Chicago, the Art Institute of Chicago, and the Adler Planetarium is included in the Chicago CityPASS.
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.
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. However this can be pricey, which is why I suggest walking along the walkway to explore the architecture on foot instead.
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.
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.
My must-have Chicago accessories:
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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.
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.
Free admission to the Shedd Aquarium and the Field Museum is included in the Chicago CityPASS.
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.
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.
Free admission to the Museum of Science and Industry is included in the Chicago CityPASS.
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 visit.
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.
Free admission to 360 Chicago is included in the Chicago CityPASS.
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.
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.
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.
As your last evening in Chicago, you have a few options to finish off your visit.
For music lovers, head to Andy’s Jazz Club or Blue Chicago to listen to some of the best blues musicians that Chicago has to offer.
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.