Visiting the windy city has always been on my travel bucket list, but when we had the opportunity to go I really had no idea what to expect. How can the third-largest city in the USA, not to mention a city with one of the highest murder rates, be a great place to holiday?
Well, I am happy to tell you Chicago is most definitely a place worth going to!
What to Expect
Between the amazing architecture, the many parks, and the sandy shores of Lake Michigan, it’s truly a beautiful city. And despite being known for high crime rates, I felt completely safe wandering around the city centre (helped, I’m sure, by the police presence everywhere you go).
Have I mentioned the food? The locals know how to eat well! Every restaurant we dined at had amazing food and fantastic service.
There is just so much to see and do, even a week isn’t long enough to take everything in.
Yes, I was absolutely smitten with Chicago. It’s pretty easy to see why visitors fall in love with this great city so easily.
Whether you are travelling to Chicago with your family, or as a couple, (and in no particular order) here are Chicago’s ‘Not to be missed sights’.
Chicago Must-Sees
1. Architecture Boat Tour
Cruise along the Chicago River and gain knowledge of the world-renowned landmarks set before you. There are quite a few different companies that do the river tours, and I am sure any of them would suffice. We went with Shoreline Sightseeing, and we were extremely happy with our guide and the wealth of information he gave us about each building we cruised by.
Tip: Choose a cruise that starts just before dusk, that way you get to see the buildings in both the daylight hours as well as lit up at night.
2. Visit the Parks
There are several parks scattered throughout the city-core and they shouldn’t be missed. Many of Chicago’s parks have an unprecedented combination of stunning architecture, sculptures, and landscape design. The ‘Bean’ (above), as it is locally known (much to the chagrin of the artist), is located in Millennium Park, and is a sight to see for sure.
Tip: Go up close to The Bean and take a photo of your reflection. It makes a really neat souvenir photo!
3. Take in a Ball Game at Wrigley Field
When in Chicago do what the locals do and watch the Cubs at Wrigley Field. Although most games sell out rather quickly, we were able to score Cubs tickets online at StubHub. Neither one of us are baseball fans, however, it was something we thought we should do. It was next to impossible not to get excited along with the crowd. By the end of the game, we too were singing along to the “Cubbies” tune.
Tip: Make it truly authentic and eat a “Chicago Dog” while watching the game. Just beware, don’t grab your meal at the first concession stand you see. Make sure to walk the entire stadium before making your choice, for each concession offers something a little different.
4. Stroll along the River
This relatively new pedestrian waterfront walk is located on the south bank of the Chicago River in the heart of downtown. It currently spans from Lake Shore Drive to LaSalle Street (with further expansion coming later this year). Nicknamed the city’s ‘Second Lakefront’, the Riverwalk contains restaurants, cafés, seating, boat rentals, and a few other activities.
Tip: Buy a glass of your favourite vino at the City Winery and grab a stool overlooking the river. It is the absolute perfect spot to sit, people watch, and enjoy the view!
5. Go to a Museum
Chicago has many amazing museums! Although time didn’t allow for me to see them all, the ones I did go to were more than worth the money. Here are my top recommendations:
- The Field Museum – this massive natural history museum has more than 30 permanent exhibitions covering 300,000 square feet, as well as special exhibitions that come and go. You can easily spend an entire day here!
- Art Institute of Chicago – With more than 300,000 artworks and artifacts from all over the world and every era, this is another museum you need a full day for. My absolute favourite display was the Thorne Miniature Rooms.
- Driehaus Museum – a decorative arts museum housed in a mansion. It’s a fascinating view of one of the few remaining examples of the palatial homes erected by the wealthy in America’s ‘Gilded Age’.
Tip: If you plan on doing the self-guided tour at the Driehaus Museum, go for the audio guide. It’s an extra $5, but it will give you some great information.
6. Tour the Chicago Theatre
If you are unable to see a live performance at this iconic building (or even if you do), go behind the scenes of the Chicago Theatre. The guided Marquee Tour allows you to experience one of the country’s last remaining movie palaces. Stand on the world-famous stage, view the autographed backstage wall, and explore the beautiful interiors.
Tip: We were able to get tickets just prior to the tour starting. Tours run daily at 12 pm.
7. Take in a Bird’s Eye View
At the 360 Chicago Observation Deck, you will head to the 94th floor to experience a breathtaking view of Lake Michigan and the cities magnificent skyline.
Tip: As the observation deck is enclosed, you are taking pictures through glass. This obviously works during the day, for the photo of Navy Pier above was taken that way. However, I do wonder if trying to take photos at night would have different results. I have a feeling you would see more of your reflection in the picture than anything else.
Source – Chicago Genie
8. Walk the Magnificent Mile
Sure this shopping district has all the same high-end stores any other big city has, but the shops on the Magnificent Mile are also surrounded by amazing architecture, fantastic places to eat, and cream of the crop hotels. Some of Chicago’s well-known attractions and destinations (many of which I mentioned above) are also located around the Mag-Mile. Trust me, this is the place to be!
Tip: Unless money is no object for you, I’d advise doing more window shopping and sight-seeing than anything else.
Top 5 things to do with Kids while in Chicago
#1 – Lincon Park Zoo – Founded in 1868, Lincon Park Zoo is one of the oldest in the US. Kids can take a spin on the carousel, ride the animal-themed express train, and view animals from far reaches of the globe. The best part? Admission to the zoo is FREE!!
#2 – Shedd Aquarium – With 32,000 animals, it is the largest indoor aquarium in the world! Explore touch-pools, award-winning exhibits, and hands-on activities, as well as view shows and 4-D movies.
#3 – Adler Planetarium – Home to over 35,000 square feet of exhibits, the Planetarium’s galleries provide a passageway to explore the universe.
#4 – Children’s Museum – Located in the Navy Pier, this interactive museum is a great place for kids to create, explore, play and discover.
#5 – Navy Pier Park – Head to the Navy Pier and hit the rides! There is a wave swinger, carousel, tower ride, remote control boats, and a new state of the art Ferris Wheel (set to open summer 2016).
Recommended Hotel
During our time in the windy city, we stayed at the Virgin Hotels Chicago. From the impeccable service from staff to the awesome choices of (extremely reasonable) mini-bar snacks and drinks in our room, our time at this hotel was absolutely incredible. I highly recommend checking it out.
More Hotel Options
Use this handy map to find many more hotel options
Booking.comSo tell me, have these Chicago must-sees enticed you to holiday in this fun city?
If you’ve been, please let me know if I have missed any of your favourite spots.
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