As the third most populous city in the USA, Chicago has a lot to offer locals and tourists alike. Traveling during the off season is one of the best ways to save money and get a new perspective of the city. Winter is one of my favorite times to visit Chicago and I love seeing the city lit up for the holidays.
Besides indulging in its delicious deep dish pizza and ice skating in Millennium Park, here are ten reasons why Chicago is the perfect winter destination!
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Table of Contents
1. Affordable hotel and airfare prices
Whether you choose to fly into O’Hare or Midway airport, most airlines offer discounted rates to Chicago during the winter months.
Hotels are also offering promotions or affordable packages during this time which makes Chicago a great winter destination if you’re on a budget.
One of my favorite ways to save money on accommodations is to book through Booking.com. This is my go-to website for finding hotels deals.
2. Tourist attractions are less busy
I have been to Chicago four times now (during both the summer and winter months). While the summer weather is beautiful, winter is my new favourite time to visit Chicago.
Tourists attractions were considerably less crowded. When I went during the summer, there was over an hour wait to get into the Shedd Aquarium, but on a weekday in December it felt like we had the place to ourselves.
Getting the most bang for your buck is my #1 factor when planning a vacation and the Chicago CityPASS was rated the #1 Chicago tourism pass by TripAdvisor.
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.
Here’s what’s included in the Chicago CityPASS:
✓ FREE entry to Chicago’s top 5 paid attractions
✓ Valid for 9 days
✓ Save 50% compared to purchasing tickets at each attraction
✓ Mobile or printable pass option
The Chicago CityPASS is a pre-paid booklet of tickets which gives you FREE fast-track entry to the following attractions:
- Shedd Aquarium – Priority Entry
- Skydeck Chicago – Fast Pass
- The Field Museum – VIP Entry
- 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.
How to get your Chicago CityPASS:
Step 1: Head to the Chicago CityPASS 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.
Check out my honest review of the Chicago CityPASS here.
My must-have Chicago accessories:
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3. The city is lit up for Christmas
Chicago is absolutely beautiful during the holiday season. There are Christmas trees decorated and lights filling the streets with holiday cheer.
The Lincoln Park Zoo puts on a festive light display which is great fun for all ages (plus it’s free).
Chicago also stages a Christmas Market in the weeks leading up until Christmas Day which is modeled after the ones in Germany.
4. Ice skating in Millennium Park
There are a number of outdoor ice rinks in Chicago but my favourite is the one in Millennium Park. It’s surrounded by trees decorated with lights and sits underneath the famous bean.
After an evening of ice skating, warm up with a cup of delicious hot chocolate at one of the nearby cafes.
5. Shopping on Michigan Avenue
Michigan Avenue offers a number of shops from high-end to high-street fashion.
Stay warm in one of the three malls along the Magnificent Mile and if you’re visiting in December make sure to check out the amazing Christmas tree at the 900 North Michigan Shops.
6. Your photos will look unique
When visiting in the summer months, my photos showcased beautiful blue skies and were inevitably filled with tourists.
One of the great things though about visiting during the winter months is being able to capture photos with snow or like this one of me alone at the bean.
7. Marvel at Chicago’s architecture
One of my favourite aspects of Chicago is its beautiful architecture. I love standing on the bridge over the river and gazing at all the amazing buildings around me.
A trip to Chicago is not complete without a visit to the Skydeck at the Willis Tower. Arrive just before it opens and you’ll be able to enjoy the glass box before too many tourists get there.
PRO TIP: You can visit the Skydeck for FREE with your Chicago CityPASS. It includes two visits to the top. Enjoy unparalleled 360-degree views during the day and again at night when the city is lit up!
8. The neighborhoods (outside of The Loop)
Like all major cities, one of the best tips I can give is to check out the neighborhoods that lay outside of the downtown core.
This is a great way to experience how the locals live and you just might fall in love with a new restaurant or park. I enjoyed exploring Wicker Park when I was visiting Chicago. We loved the cute cafes and shops in the area.
9. Enjoy the city’s public art
Chicago is full of beautiful displays of public art which makes it a unique city. Bundle up and take a walking tour around the Loop to check out sculptures, architecture, bridges and monuments.
End your walking tour by exploring the Art Institute of Chicago. Here you will find some famous paintings by Picasso and Monet. This is one of the oldest and largest museums in the United States. It’s also rated the #1 attraction to visit in Chicago on TripAdvisor.
This is the perfect way to spend an afternoon staying warm indoors and looking at beautiful artwork from Greece, Africa, Japan, and the Americas.
PRO TIP: You can visit the Art Institute for FREE with your Chicago CityPASS. It includes FAST PASS entry so you can skip the line and spend more time sightseeing.
10. Watch a theatre production
Enjoy an evening seeing one of the many theatre performances Chicago has to offer.
Whether you choose a musical or play in the downtown area or explore one of the resident theatre companies in Chicago, it will definitely be an evening to remember.
If you’re in the mood for comedy, don’t miss a visit to Second City which originally opened its doors in 1959 and has become the most influential comedy theatre in the world.
