8 Great Reasons to Visit Chicago in the Winter

Last November we went on a little couple’s getaway to Chicago. While this blog is definitely geared toward family vacations, a couple’s retreat is pretty essential for the whole family!  Happy mom and dad = happy kids 🙂  Now, November + Chicago might seem crazy with the frigid winds and looooow temps, but it was actually amazing! We would highly recommend this time of year for many reasons. Here’s 9 reasons why:

1.Willis Tower. 

There’s no better way to see the windy city than from atop the windy city.

We cruised right to the top of the Willis Tower in November. During peak season, the wait time can be anywhere from 45 minutes to two hours. We had no wait time at all–a big bonus for Emily, who is scared to death of heights! Had there been a long wait, the anticipation might have been just too much 😉  Cruising up the 103 floors to the top of the tallest building in the Western Hemisphere takes a mere 90 seconds–that’s 16 feet per second! From there you’ll be able to take in the stunning views of the Chicago skyline and have visibility of up to 50 miles. Pretty cool to be able to see four states–Illinois, Indiana, Wisconsin, and Michigan.

When we visited on a somewhat foggy day during the end of November, the views were still impressive.


It’s honestly a little crazy stepping out into a glass box at the Skydeck, but you have to do it! You’ll also be able to wander the entire top floor and take photos from all angles.



Tickets are $22 for adults and $14 for kids, but discount tickets can be purchased at neighboring businesses. We ate lunch at Giordanna’s and purchased discount tickets there.

2. Soldier Field or Wrigley Field.

Touring either one of these iconic sports stadiums will not only fill you with an appreciation for Chicago’s sports teams, but will fill you with a greater love for the city. For us, taking a tour of Soldier Field from a retired Chicago police officer was pretty cool and we learned a lot of the history, culture, and more. The tour was $20 per person, and well worth the admission. We were able to go down to the field (but not out onto the field), tour the visitor’s locker room, enjoy views from the corporate suites, and walk throughout the concourses and exterior parts of the stadium. And who knows, maybe the Bears will once again be competitive. Regardless, this tour actually has me rooting for Da Bears! Now that the Cubs finally won the World Series, I would imagine more people will flock to the Wrigley tours.



Yes, ladies! It really is a wonderful experience to tour Soldier Field. Even if you’re not a huge sports fan, you will enjoy the history this stadium has to offer.



3. The Art Institute of Chicago.


Located in Chicago’s Grant Park, the Art Institute of Chicago features a collection of Impressionist, Post-Impressionist, and American art. Highlights include paintings by artists including Claude Monet, Vincent van Gogh, and Georges Seurat. Seeing Seurat’s large painting of A Sunday Afternoon on the Island of La Grande Jatte was really cool. It was larger than life, sized at roughly 7 feet by 10 feet.




Grab a brochure from the front desk which will have a map featuring the most popular pieces of art that you’ll for sure want to see.




There are a few different ticket options:

General Admission (which we did): $25 for adults, $19 for seniors, students (must show school ID) and teens. Children are free.

Fast Pass:$35 for adults, $29 for seniors, students (must show school ID) and teens. Children are free.

They also offer a combo ticket for the Art Institute + SkyDeck for $45 per person.

Visit Art Institute of Chicago for more information.

4. Visit and see Chicago’s cool architecture.

Cloud Gate, better known as The Bean because of its shape, is such an interesting sculpture offering great photo options from every angle. Sculpted by Indian-born British artist Anish Kapoor, it is the centerpiece of the AT&T Plaza at Millennium Park. The sculpture and AT&T Plaza are located on top of Park Grill, between the Chase Promenade and McCormick Tribune Plaza & Ice Rink (more on that below).



Wrigley Building, Tribune Tower, and the “corncob towers” (and many others) will leave you in awe as you stroll the streets of Chicago. Downtown was so festive with the holiday season right around the corner.

Be sure to bundle up! Emily forgot her to wear her hat our first evening exploring and we ended up swinging by a CVS to buy a hat. The wind definitely bites at your ears, so warm clothing at all times is a must!




We hopped aboard a yellow Chicago Water Taxi for a quick 20 minute cruise down the Chicago River.  It was just the two of us (yay November!), making it a rather fun & romantic way to see the city. Tickets start at only $4 per person one way or $8 for the entire day!  There are several stops if you choose to get on and off, including a stop right across from our hotel making it super convenient. For more information, visit their website.



5. The Chicago Theatre.

Nothing will put you in the holiday mood like a wonderful show at the historic and beautiful Chicago Theatre. While we were there, How the Grinch Stole Christmas was playing. It was a charming show with fun musical numbers, costumes, and effects. Great for all ages.

This iconic theater is located on North State Street in the Loop area of Chicago. Rudolph the Red Nose Reindeer played in November 2016.

For the latest information, including performance schedule and ticket costs, visit their twitter feed or  website.

6. Ice skate in the heart city. 

The rink, located on Michigan Avenue between Washington and Madison Streets, sits just below the iconic ‘Bean’ statue.

The Bean-Chicago  

If you want to make your sweetheart feel like she is the star of her own chick-flick, then definitely take her ice skating! There is something completely magical about ice skating in the heart of Chicago, with the skyscrapers as a backdrop and the twinkly lights of the season all around.

The Millennium Park – McCormick Tribune Ice Rink typically opens the second week of November and remains open until March. It is free to ice skate, however skate rentals are $12 per pair.

For more information, visit their website. 

7. Shopping the Magnificent Mile.


There are more than 400 stores to choose from as you stroll up and down the 8 blocks and 3 malls that make up the Mag Mile. There is literally a store for everyone, from every price point, making this perfect place to do holiday shopping, or any shopping! 🙂

Emily’s personal favorites?  ZARA, the two-floor City Target (have I mentioned I enjoys long walks through Target?!), H&M, The Disney Store, American Girl Place, The LEGO Store, and Candyality.



Target is a great place to buy your favorite teams sport’s apparel and paraphernalia. They had a variety of hats, shirts, jerseys, and other items at a great price. When we were there, they had a huge selection on the first floor near the doors.



Notable stores include: Crate & Barrel, Room & Board, Home Goods, Lululemon Athletica, Nordstrom Rack, Bloomingdale’s, Nordstrom, Macy’s, Neiman Marcus, Saks Fifth Avenue,  Burberry, Bottega Veneta, Bulgari, Chanel, La Perla, Louis Vuitton, Ralph Lauren, Giorgio Armani, Cartier, Rolex, David Yurman, Swarovski,  Tiffany & Co., Gucci, Michael Kors, , Montblanc, Williams-Sonoma, L’Occitane, MaxMara, BOSS Hugo Boss, Armani Exchange, Louis Vuitton, The Art of Shaving, Kiehl’s, Vosges Haut-Chocolat,  Sephora, NIKETOWN, Apple Store,  Columbia Sportswear, Forever 21, Old Navy and so many more.

For a complete list of stores and dining options, visit their website.

8. The Lights Festival


We were so sad to have missed this amazing festival + parade + firework spectacular by 1 (one!) day. It is definitely on our list the next time we go and 2017 would be the perfect time.


This amazing festival celebrated its 25th anniversary this past year on November 19th. It would be a great outing for the entire family to attend!

Image Credit: Mag Miles FB Page

For more information, visit their website. IMAGES|Magnificent Mile FB Page

9. And of course we can’t forget the food we ate while we were there. To see a complete list of our can’t-miss Chicago eats, click here. 

Well, that’s how we did a weekend in Chicago! How do you?? When is your favorite time to visit the Windy City?