How to Spend a Romantic Honeymoon in Chicago

Thank you to Chevrolet, Museum Hack, Marriott, CityPASS, Chicago’s First Lady Cruises and Bistronomic. While they provided us with complementary experiences, these opinions are our own.

If you are looking for a romantic getaway or honeymoon in a big city with plenty to do and explore, Chicago may fit the bill. The city is full of attractions including world class museums, huge beautiful parks, delicious food and much more. Here are our recommendations on what to do when you go to Chicago.

Getting around Chicago

If you plan to stay in the city, and especially if you’re staying downtown, you will likely be fine taking an Uber or public transit. These options are usually less expensive than renting a car.

However, we planned to take a trip outside of the city so we knew we needed a car. For this trip, Chevrolet loaned us the all-new 2019 Chevy Blazer, a sportier and more stylish version of the car previously called a Blazer in the 90s. We honestly had so much fun hopping into the bright red, decked-out car. If you do decide to rent a car, it can sometimes be worth spending a little more for something fun.

We quickly learned, though, that parking in the city is crazy expensive. We are talking $60+ for overnight parking at many hotels. That is when I found the app, Spot Hero. It showed us a parking garage in Chicago that offered 3 days of parking for $13, 2 blocks from our hotel on the Magnificent Mile. That same garage’s website showed a parking cost of $50 a day, so the app saved us a lot of money.

Stay in a high rise hotel

Chicago’s skyline and architecture is iconic and there are few cities in the world with accommodations in such high rises that give you such great views.

For our trip, we stayed at the newly renovated Chicago Marriott Downtown Magnificent Mile.

From our suite on the 44th floor we enjoyed an amazing view of the city below. It is located walking distance from many of Chicago’s highlights like the Navy Pier and Millennium Park, so we were right in the middle of the action.

Additionally, the new bar Reviver has created a drink menu that takes you through the history of Detroit, including the Prohibition era, with complex non-alcoholic drinks for babymooners or people like us who do not drink.

Enjoy eating at a romantic restaurant

Chicago is full of amazing restaurants. While you must try out Chicago’s staples, like deep dish pizza and a Chicago-style hot dog, also make sure to plan an evening for a romantic dinner. With a list of over 20 Michelin-rated restaurants and even more just as delicious places to dine, you’ve got a lot of options to choose from.

We tried Bistronomic, a modern French bistro located one block away from the Magnificent Mile. The restaurant feels cozy, has a menu using fresh and local ingredients, has quality service and most importantly has delicious food.

We tried the seared scallops, which were cooked and seasoned perfectly, as well as the Amish chicken. For dessert, the baked Alaska stole the show.

Later in our trip, we found our way to the Little Italy neighborhood of Chicago and ate dinner at Tuscany Taylor, which features incredible, traditional Italian food. The restaurant felt so authentic, and even walking around the neighborhood gave us a sense of the rich history of the city.

Face your fear of heights at the Sky Deck

Go to the 103th floor of the Willis Tower (also known as the Sears Tower). On the Skydeck you can enjoy panoramic views of the area and the main attraction, The Ledge.

Step out onto a glass box that extends out of the Skydeck for a unique view of the city that may get your heart beating a little bit faster.

For a special evening, you can enjoy a deep dish pizza dinner from the Skydeck. The Pie in the Sky dinner experience includes the world famous Chicago-style Giordano’s Pizza enjoyed right on The Ledge

The Chicago Skydeck is included in the Chicago CityPASS so consider using that if you plan on going to the other attractions in the area.

Go on an architecture tour

Learn the history of Chicago and get to know the stories behind the many buildings along the Chicago river by going on a Chicago architecture tour.

We enjoyed the 90-minute-long boat tour with Chicago’s First Lady Cruises. You board the boats by descending down to the river walk and getting on one of the boats with open air decks and full service bars.

The guide explains the history and style of prominent buildings around the river while sharing the history and stories of the development of Chicago. We found it fascinating to see buildings from different times in the history of the city and learn about the architects.

Depending on weather, we recommend bringing sunglasses, a hat, and sunscreen to this tour, as it can get a bit sunny! It isn’t a fast boat so wind wasn’t really a factor for us.

Tour the Art Institute of Chicago

The Art Institute of Chicago is one of the world’s greatest art museums with an amazing collection from around the world, spanning centuries of time. It is often voted Best Museum in the World, rivaling The Met in New York and the Louvre in Paris.

For our trip to the museum, we explored in a unique way. Instead of taking a self-guided tour through, we took an Un-highlights tour with Museum Hack.

Museum Hack tours lead you through the museum showing you a side you have never seen before, giving you a tasting menu of the museum with unique stories about the art no one else would know to share with you. Tours are fast-paced, irreverent and even include a few games along the way.

We love going to art museums, but after a few hours of wandering on our own we often experience Museum Fatigue, where your heart wants you to keep looking and learning but your brain is overloaded with all the art and information. Museum Hack was a really fun way to see what the museum has to offer, without feeling like you’re missing something. (Missing something is kind of the point!)

We had a great time and definitely recommend it, especially if you are not an art museum fan, or if you want a good way to experience all of a museum in a short amount of time.

After the tour, we had a little bit of time before closing to go back and take a closer look at some of our favorite pieces.

Check out the world class museums & attractions

Beyond the Art Institute of Chicago, there are several other great Museums to visit.

The Field Museum of Natural History is full of educational exhibits including one about evolution which features Sue, the largest Tyrannosaurus Rex fossils. We also enjoyed the Wildlife Photographer of the Year exhibit, and the ancient Egypt exhibit that includes 23 real mummies.

At the Museum of Science and Industry there are several experiences, some of which are included with entry and some for additional cost. By using a CityPASS, we were able to choose one of the paid exhibits, and we chose to tour a coal mine. We descended into a recreation of a coal mine with real equipment and can see what it is like to be in a coal mine during different times in history. It really brought coal mining to life, and it kept us thinking for days after.

The other exhibit that stood out was the U-505 Submarine. The actual German submarine is in the museum where you learn its history and can even go on board to tour it.

In addition to museums, there is also an aquarium next to the Field Museum and a Planetarium next to that. As compared to paying for admission for each of the Chicago museums, it is much more affordable to visit these attractions with the Chicago CityPASS. Chicago CityPASS includes admission to the Shedd Aquarium, Skydeck Chicago and the Field Museum. You can then choose between the Art Institute of Chicago or the Adler Planetarium, and between the Museum of Science and Industry or the 360 Chicago Observation Deck.

Enjoy a comedy show

Did know know one of the premier comedy clubs is located in Chicago? The Second City has been around since the 1950s and since then has become one of the most iconic comedy clubs. Second City has been the launch point for stars like Dan Aykroyd, Steve Correll, John Candy, Tina Fey, Amy Poehler, Mike Myers and many more.

With shows every night of the week it is fairly easy to find tickets. We purchased tickets for $18 to see the “The Best of Second City”, a mix of scripted bits and improvisation. The performance was officially shown in two acts, but after closing bows, the cast indicated that we could stay for a bonus third act where they would be trying out new bits and practicing games. The third act was just as fun as the first two. We attended the show on our last night in the city and it was definitely a highlight of our trip.

Go for a walk in the park

Chicago has several beautiful parks to explore. Lincoln park is the largest city park along Lake Michigan. It features several harbors with boating facilities, an public beaches for swimming. There are landscaped gardens, public art, bird refuges, a free zoo, the Lincoln Park Conservatory, the Chicago History Museum, the Peggy Notebaert Nature Museum, the Alfred Caldwell Lily Pool, and a theater on the lake with regular outdoor performances held during the summer.

At Millennium Park you will find the iconic Cloud Gate, also known as “the bean”. There are hundreds of free cultural programs here including concerts, exhibitions, tours, and family activities. In the winter there is an outdoor skating rink and the annual Christmas tree lighting.

Eat Plenty of Food

There is not enough time in the world (or room in my stomach) to eat at all the highly rated places in Chicago, so we have many places left we’d like to try. With the rich history of Chicago, there are also a number of neighborhoods and cuisines we have yet to explore, like Chinatown and Greektown. If there’s a specific type of food you love, I’m sure you’ll find a delicious version of it in Chicago.

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