How to Plan a Couple’s Getaway to Chicago

Disclaimer: This post is in partnership with Digitized Adverts to highlight the beauty of Chicago & how to experience the city as a couple.

Chicago is one of the most popular cities to visit in the US but yet when you hear Chicago, you don’t tend to think of it as a romantic couple’s getaway location!

However, Chicago has so much to offer couples travelling together and it is an amazing destination to put some spark into your relationship and get to see a new city together.

From beautiful cityscapes, stunning cocktail bars, exciting activities and incredible restaurants that are perfect for candle-lit dinners, it is safe to say that Chicago should definitely be on your couple’s bucket list! Not to mention, it’s home to the deep pan pizza which is enough to make anyone’s mouth salivate…

If you’re sitting on the fence as to whether Chicago can be a romantic getaway then in this blog post you will find reasons as to why Chicago should be on your hot list. You will also find some top tips for visiting Chicago as a couple to make the most of your time together and plan for romantic, intimate experiences.

Reasons to Visit Chicago for a Romantic Getaway

As we mentioned, when you’re planning a romantic getaway, your mind drifts to European destinations such as Rome or the city of love itself, Paris (which in our opinion are not the most romantic cities to visit). However, why is Chicago not on your mind for an intimate trip away with your loved one?

Below, you will find our top 7 reasons as to why we think that Chicago is an underrated destination for a couple’s getaway and why it should be on your bucket list!

1. Beautiful Cityscapes

First of all, the viewpoints in Chicago cannot be beaten! There are so many great cityscape views where you can soak in the city with your partner and appreciate this wonderful world that we live in.

Whenever we travel anyway, we are like magpies to viewpoints especially as we love to get some great Instagrammable photos and Chicago is one of the best places to do this.

If you want to see the city from above, then visit Skydeck Chicago and step out onto “The Ledge”. Alternatively, the “TILT” experience at 360 Chicago provides a dizzying view of the city. And for the ultimate romantic experience, consider a sunset helicopter tour over the lake and the city’s landmarks.

Take in the beautiful views together and also experience a little sip of adrenaline whilst you’re at it. These are the kind of travel experiences that we live for!

2. Stunning Romantic Hotels

When you’re travelling anywhere as a couple, you always want to make sure that you find an incredible hotel, ideally with great views and that is comfortable for you both to relax after a long day of exploring.

Chicago is a perfect spot to find incredible hotels especially if you’re looking for rooms with views. If you’re feeling really fancy then you may even want to opt for a hotel that has a view of Lake Michigan.

One of the best hotels in Chicago for both quality, luxury and picturesque views is the Peninsula Chicago. This gorgeous hotel offers spa amenities, an indoor pool and from the rooftop you will find sweeping views of the lake. This is certainly a great place to stay to make your couple’s trip to Chicago extra memorable.

For budget travellers such as ourselves, you may want to opt for a more wallet-friendly option such as the Sable at Navy Pier. This is a beautiful hotel which also offers incredible views of the lake and it is also conveniently only a 10-minute walk from the major attractions in Chicago.

No matter which hotel you decide on, make sure that you are close to the main centre so that you can spend more time together than travelling across the city. As budget travellers ourselves, that is something we always consider when we are planning a trip is to ensure that we don’t end up spending more on travel costs than we would have on just booking a centrally located hotel!

3. Art & Culture Scene

As a couple, you will often have both similar and different tastes in music, art and how to spend your time. In Chicago, you will find that there is a little bit of something for everyone.

Chicago is infamous for its music scene and you will find plenty of live music bars around. For a more intimate, romantic atmosphere you may choose to visit a live jazz or blues performance in venues such as Kingston Mines of the Green Mill Cocktail Lounge.

Alternatively, you may fancy to carry on the good times and go and enjoy a comedy show instead. We actually met at a comedy club in Edinburgh so when we are travelling, comedy shows always appeal to us so that we can reminisce about when we met.

If you both love binge watching TV shows as well, you will be unsurprised to know that the incredible TV dramas ‘Chicago Fire’ ‘Chicago PD’ and ‘Chicago Med’ were mostly filmed in the city. If you’re fanatics of the show like we are then you may want to embark on a sightseeing tour of some of the iconic spots from the shows such as the firehouse 51! If you plan your trip well enough in advance, you can also sign up to be an extra on the show if they are filming at the time you’re visiting. This would be an ultimate way to capture your romantic getaway together and get some screentime in whilst you’re at it.

If Art is an interest that you both share together then you may want to go on a walking tour around the city to admire the beautiful murals and works of art present in the city. Alternatively, you may even want to hire bikes to tour the street art yourselves and take everything at your own pace.

No matter what interests you both have, you will find something and everything in Chicago to suit you both and continue to create awesome memories together.

4. World-Renowned Dining Experiences

No matter your budget, you will find some great places to eat whilst in Chicago. Home to the deep-pan pizza dish, if you’re looking for some cheap eats then you won’t need to look very far. Just because you’re eating on a budget, doesn’t mean that it doesn’t have to be romantic. Grab some pizza and head to a spot by the lake for a cheap meal with a view.

However, if you are looking for something a bit more special then you will want to book a table at LondonHouse Rooftop. Here you will find not only spectacular views with your meal but also some delicious American style tapas with some tasty cocktails to match.

If you’re looking for something a bit more intimate then you might enjoy your Chicago date night at Geja’s Cafe where you can dive into their classic fondue whilst being entertained by live flamenco dancing and music. There’s a reason that it has been voted ‘Chicago’s Most Romantic Restaurant’ and it is simply a place not to be missed!

5. Plenty of Activities

From enjoying a romantic cycle around the lake, walking tours, sunset cruises along the lake to even relaxing at one of Chicago’s beaches. Yes, that’s right Chicago even has its own beaches! There is so much choice of things to do in Chicago that you really couldn’t go wrong.

For any couple, you will find an array of activities to enjoy together whether you’d like to sample a hint of adrenaline at the “TILT” experience at 360 Chicago or relax with a cocktail at one of the many rooftop bars.

You can head into a secret speakeasy like Violet Hour and feel like you’ve been transported back in time or embrace the modern world by experiencing the interactive art of Millenium Park’s ‘The Bean’.

Plan your adventure just how you like it and experience unforgettable memories with your loved one along the way!

Tips for Planning Your Couple’s Getaway to Chicago

Chicago can be just as romantic as a 4-day trip to New York City, if not more so, with the right planning. Here are our top tips to make your getaway extra special:

1. Plan in Advance

Chicago is a busy city and if you’re budget travellers like us, you’ll always be looking at ways to save money. Planning your trip in advance can make sure that not only do you access the best fares but it also gives you more time to pay it up which means that there’s more money in the travel pot for you to spend on experiences that you are going to enjoy together.

2. Look for Romantic but Central Hotels

Don’t waste time travelling back and forth between your hotel and Chicago’s attractions. Try to stay as central as possible that is within your budget but also look out for romantic highlights in a hotel such as a good view, comfy or luxurious amenities as well as somewhere you will feel like you’re in a home away from home.

When choosing your hotel in Chicago make sure that you choose your accommodation wisely and spend time researching what is right for you both.

3. Plan a mixture of activities

Take your time in Chicago and don’t try to jam pack too much in because then it doesn’t become a romantic getaway and more of ticking off items on a list.

There is so much to see in Chicago so narrow down what is important for you both to see and combine a mixture between sightseeing and intimate experiences so that you can sample the best of what Chicago has to offer.

4. When do you want to visit?

Chicago is a great all-year-round destination with activities such as ice skating in the winter, beaches in the summer so think about what kind of trip you’d like for your couple’s getaway to Chicago and plan it around that.

Don’t forget to think about festivals such as St. Patrick’s Day where the river is dyed green in honour of the occasion and this is the only time of year you can see this!

Depending on what time of year you plan to visit Chicago will depend on what activities you can do and your experience whilst you’re there so that’s why planning in advance will help you make your trip to Chicago, the best that it can be!

5. Consider combining Chicago with other US Destinations

If you’re planning a trip to Chicago then you will most likely want to spend around 4 – 5 days there. However, if you’ve got more annual leave than that, why not combine it with another city and tick two off your bucket list at once?

Make it into a couple’s exploration vacation and combine Chicago with another city such as New York City, San Francisco, Nashville or even Miami. The world is your oyster!

Plan Your Couple’s Getaway to Chicago Today!