Fun Valentine Staycation Ideas in Chicago (+ 3 Itineraries)

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Every day is a wonderful time to celebrate love and spend a romantic evening with your special someone. With these Valentine staycation ideas in Chicago, you can make it extra special with our suggest itineraries.

In this post, we share a few staycation itineraries for couples and with kids.

What is a Staycation

A staycation is a vacation spent at or near one’s home. So instead of spending extra money on airfare or car rentals to travel to a distant location, spend it nearby in Chicago!

Luxurious amenities, comfortable accommodations, and romantic settings can be found in the great city of Chicago. You can find select star hotels, spas, vacation rentals, as well as bed and breakfasts. Be sure to check for Valentine’s Day specials.

A Valentine Staycation Itinerary for Couples


For a romantic staycation, we recommend the InterContinental Hotel. The hotel location is right on the Magnificent Mile and the service is exceptional. Amenities include luxury linens, an onsite spa, and a phenomenal pool.

For a luxury option, stay at the Waldorf Astoria. This five-star hotel is located in the Gold Coast neighborhood and has stunning views of the city. In addition, you’ll have access to a spa, fitness center, and fine dining. 

For couples looking for a more intimate setting, we recommend the Hotel Lincoln. This boutique hotel has a rooftop terrace and a cozy fireplace in the lobby. It is an excellent location for things to do on during your Valentine staycation in Chicago. 

Another option is to rent a vacation home or an apartment. This will give you privacy and space to plan a romantic getaway the way you envision. Chicago has plenty of vacation rentals in the city, from luxurious lofts to charming brownstones, or chic Michigan Avenue apartments.

Where to Stay

Couples celebrating love during their Valentine’s Day is an important tradition and a staycation together can elevate the holiday to an even more special and memorable experience.

InterContinental Hotel Chicago | 7.9 Good | $$$ |

Waldorf Astoria | 8.0 Very Good | $$$

Lincoln Hotel | 8.0 Very Good | $$

Sentra Michigan Ave Apartment | 9.1 Wonderful | $$

1-Day Itinerary of Activities and Experiences

Start your valentine staycation with breakfast in bed or try one of Chicago’s best breakfast houses.  

Treat your sweetie to a shopping spree at 900 North Michigan or the Water Tower Place. Or stop at the Shops at North Bridge and then enjoy a coffee break at the world’s largest Starbucks

📍Water Tower Place | 835 Michigan | Sat 11 AM – 8 PM, Sun 12 – 6 PM

📍The Shops at North Bridge | 520 N Michigan | Sat 10 AM – 8 PM, Sun 11 AM – 6 PM

📍Chicago Reserve Roastery | 646 N Michigan | Sat & Sun 8 AM – 9:30 PM 

Indulge in a luxurious spa experience for two at your hotel.  

📍Spa @InterContinental | 505 N Michigan | 8 AM – 8 PM

📍Spa @Waldorf | 11 Walton St | 8 AM – 8 PM

Take a stroll along the Chicago Riverwalk and find a spot for lunch.

📍Riverwalk (Wacker and Michigan Aves) 

Cruise the Wendella for an architectural tour. If you can’t make one of the earlier architectural tours, a sunset cruise on the Chicago River and Lake Michigan is a romantic option for couples. 

📍400 N Michigan Ave

After a sunset cruise, you can stop at City Winery Riverwalk for entertainment and cocktails. Check the website for weekend performances. This year, Sheila E and the E-train is performing on February 14th!

📍 11 E Riverwalk South

For more options, view our video selection of romantic restaurants in Chicago.

A Galentine’s Staycation Itinerary

The best thing about being single is that you can enjoy your freedom and independence with your bestie.

Although Galentines’ Day is normally celebrated on February 13th, any day is a perfect day to celebrate female friendships, have big belly laughs together, show support, and nurture one another.

This day is about brunch, spas, and outings! You should also plan to exchange a small gift to show appreciation and let your bestie know how special she (or they) are.

Where to Stay

We are all about comfort when making Galentine plans. We love the Palmer House. The historic hotel is located in Chicago’s theater and district where there are tons to do and see. The lobby oozes with charm from another era and you won’t have to go very far for great shopping experiences or spa services.

We also recommend these hotels for easy access to everything that makes Chicago great!

Palmer House | 7.6 Good | $$

The Pendry | 9.0 Wonderful | $$

theWit Chicago | 8.2 Very Good | $$

1-Day Itinerary of Activities and Experiences

After a delicious Chicago breakfast, you can do some shopping on State Street. You’ll find great deals at Primark, it’s affordable and has a friendly environment. Most of the shopping can be found between Adams (south) and Lake Street (north). The indoor mall, Block 37, and Macy’s are not to be missed.

Stop at Garrett for some delicious Chicago mix of sweet and savory gourmet popcorn. 

📍26 W Randolph | Daily 10 AM – 7 PM

Visit the Art Institute of Chicago for a journey through art and history. You’ll see curated artwork in this privately owned gallery. The Thorne Miniature Rooms are a must!

📍111 S. Michigan Ave | Sat & Sun 11 AM – 5 PM

A stop at the Bean, or Cloud Gate, for your Galentine selfie is a great way to seal the memories and honor your friendship.  

📍201 E Randolph (Millenium Park) | Daily 6 AM – 11 PM

It wouldn’t be a Galentine’s celebration without a chocolate splurge! Stop at Ghirardellis for rich, creamy ice cream topped with hot fudge and whipped cream. Or visit the Nutella Cafe for gelato or a Nutella Mocha Latte.

📍Ghirardelli – 400 N Michigan | Fri & Sat 10 AM – 11 PM, Sun 10 AM – 10 PM

📍Nutella Cafe – 189 N Michigan | Sat 10 AM – 9 PM, Sun 10 AM – 7 PM

Indulge in an afternoon spa experience at the Palmer or theWit.

📍Spa @theWit  201 N. State Street | Th – Sun 10 AM – 5 PM

📍Spa @PalmerHouse 17 E. Monroe Street | Sat 10AM – 6PM, Sun 11 AM – 6 PM

Evening dinner and cocktails at Cindy’s Rooftop. It’s one of the best rooftop bars in Chicago and a great place for socializing.  

📍12 S Michigan | Sat & Sun 10 AM – 12 AM

A Valentine Staycation Itinerary with Kids

Valentine’s Day is not just for couples! Families with children can celebrate it too with a staycation in Chicago! You’ll enjoy being away from the routine of weekend chores (and we’re sure they will be too).  

We recommend the Embassy Suites for all the great amenities, like separate living areas, that a family could enjoy. The hotel property features on-site restaurants, fitness centers, and swimming pools!

They also offer free made-to-order breakfast in the morning, and receptions in the evening (with complimentary drinks and snacks). It’s great for families or a group of friends traveling together.

Where to Stay

For a family staycation with kids, these hotels are also great options. They have nice suites and are close to the Magnificent Mile

Embassy Suites | 8.0 Very Good | $$

Millennium Knickerbocker Chicago | 7.3 Good | $$

DoubleTree Chicago Magnificent Mile | 8.2 Very Good | $$

1-Day Itinerary of Activities and Experiences

After breakfast, start your day with a Chicago Scavenger Hunt. You’ll enjoy being outdoors while solving clues together and learning about Chicago.

Visit American Girl Place where kids can shop for dolls and accessories, participate in craft activities or have a meal at the cafe.

📍835 Michigan Ave | Sat 10 AM to 7 PM, Sun 11 AM to 6 PM

Visit the Museum of Ice Cream for a hotdog ice cream! You’ll experience six rooms of exhibits, a sprinkles pool, a hot chocolate cafe, and fun ice cream trivia. 

📍435 Michigan Ave | Sat & Sun 10 AM to 7 PM

Stop at the Lego Store and get creative! Kids can build and play with legos and attend lego-building classes. 

📍835 Michigan Ave | Sat 11 AM to 8 PM, Sun 12 PM to 6 PM

On the 360 Chicago observation deck, you’ll see sweeping views of Chicago above the lake and the city. Add admission to the TILT for an exciting experience of facing downward from the 94th floor. 

📍875 North Michigan Ave | Sat & Sun 9 – 11

Final Thoughts about a Valentine Staycation

Whatever your choice of itinerary, a Valentine staycation in Chicago is a great way to spend the day with your loved one.

You can enjoy all the comforts of home, while still feeling like you’re on vacation.

Here are some more resource that you might enjoy:

Enjoy the cool weekend in Chicago and spread some love!


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