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Couple’s Getaway Itinerary

Written By: Jessie White

It feels like Valentine’s Day sneaks up on us faster every passing year and 2020 has been no different. The card aisles have transformed into their classic shades of red and pink and the teddy bears seem to have tripled in their typical size, so the question of what to do for your significant other has likely been a pot beginning to boil on that back burner. Every couple is different, some couples like to keep things simple with a pint of ice cream with their first date film or maybe they check out a cool new restaurant. Some years you want to make things extra special, and that can feel like an overwhelming question of “What do I get them?”

However, something proven to make any date extra special is to think instead, “What should we experience together?” That’s why we think that one of the best things you can do with your partner is to go on a trip where you get to leave all the daily annoyances behind and focus on enjoying each other’s company. Explore a city together and make new memories within a different landscape. A city that we have some obvious love for that’s perfect for a couple’s getaway is Chicago. We wouldn’t even be able to list all the reasons it’s an awesome place to spend Valentine’s Day. Beautiful scenery? You’ve got it. Awesome history and architecture? We define it. Amazing food? Duuuh, don’t even get us started.

So what do you do while in the Windy City with your loved one? Well, we have the perfect answer right here for the perfect quick trip to Chicago with your loved one. Whether you can check out the city for a day or a whole week, these are some of the most romantic ways to spend time in the Second City.

Taste all the Hype on a Food Tour

Chicago Loop

Chicago is made famous by a ton of amazing things like architecture and the city’s rich history but it’s been made popular for the flavors that come out of this melting pot of a metropolis. A walking food tour is an amazing way to see the popular Chicago landmarks while also getting to taste what makes “Chicago-style” so well loved and enjoyed. This food tour features all of the Chicago “classics” such as deep dish pizza, Chicago-style hotdogs, Italian beef, and more.

Reserve spots on the Chicago Favorites Walking & Food Tour here!

Stroll along Lake Michigan at the Lincoln Park Zoo

2001 N Clark Street

Chicago is often referred to as the “City on the Lake” and the gorgeous views along the Lake Michigan coastline can easily make you understand why. The Lincoln Park Zoo rests along the shore of Lake Michigan which provides a perfect way to explore Lake Michigan. First, check out the free exhibits at the Lincoln Park Zoo to take advantage of Chicago’s free zoo. Get a photo together at the Nature Boardwalk and then head east toward the Lake to follow the Lakefront Trail while you and your partner enjoy some relaxed conversation along the coast.

Take Advantage of Chicago Theatre Week

Various Theatres

 The eighth annual Chicago Theatre Week presented by Choose Chicago will luckily take place during the Valentine’s holiday this year so take advantage of reduced admission to select shows all over the city. Whether you want to make your sweetheart cry laughing at The Second City or you want to see an off-broadway preview in the Cadillac Palace Theatre, Chicago Theatre Week is designed to give interested audience members the opportunity to see amazing theatre for an even more fantastic price.

Tickets and Showtimes for Chicago Theatre Week can be found here.

Ice Skate at Millennium Park

201 E Randolph Street

 If you’re looking for the quintessential Valentine’s Day you’ve simply got to take your special someone to an ice skating rink for the perfect excuse to hold hands. The Ice Skating Rink at Millennium Park sits right in front of the famous Cloud Gate, giving your skate date the perfect romantic backdrop to create new memories in front of The Bean.

Cozy Up at Bombobar

Bombobar is every Instagram-loving foodie’s dream-come-true. Both Chicago locations boast some of the best doughnuts in the city as well as gelato, coffee, and rotating cocktails. The Old Town location is a beautiful date spot that is the perfect place to try the famous “bomboloni”, a holeless Italian doughnut with various infusions inside. Perfect for Valentine’s Day are Bombobar’s “Hotter Chocolates” that are larger-than-life hot chocolates sure to warm even the coldest of hearts on Valentine’s Day.

A full menu of everything that Bombobar has to offer can be found here.

Surprise them with a Hotel Reservation

One of the most romantic things you can do for your significant other is surprising them with more time spent in Chicago. Many hotels feature special Valentine’s Day promotions with discounted rates and most of these hotels will also feature “romance packages” with champagne, roses, and more. A boutique hotel is a charming way to stay cozy with your loved one while ditching the mega-hotel prices and all of the hotels listed below will give you an experience you’ll never forget.

Need Hotel Accommodations?

The Willows Hotel

Located at the edge of Lakeview and Lincoln Park, accessible via Brown Line train

The Majestic Hotel

Located in the heart of Wrigleyville, accessible via Red Line train

 The City Suites Hotel

In the heart of Boystown, accessible by the Red Line train

The Ivy Hotel

Located near the Magnificent Mile in Chicago’s Loop

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