Chicago is one of the top destinations in North America when it comes to both business and pleasure. Couples looking for a romantic getaway will be happy to find an almost endless list of possibilities in the Windy City. You could wander around Lake Michigan’s shoreline, explore the many gourmet options and Viator tours, or check out the Magnificent Mile. If you’re looking to surprise your partner with a romantic gesture, you could try taking a carriage tour of Michigan Avenue, hop on the Navy Pier Ferris Wheel, or head over to 360 Chicago, for breathtaking city views. There are also countless restaurants with a view where you can treat your partner. If you want to take a break from all the outdoor activities, stay in your hotel room and relax with a spa massage, have a drink on the rooftop bar, or check out the pool, read on, as we’re about to show you the best romantic staycations in Chicago, Illinois.
We handpicked these listings carefully, considering (wherever possible) recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to couple-friendly amenities and activities. The image galleries get refreshed with the latest updates regularly. They were last updated on April 07, 2024.
1. Villa D' Citta (from USD 205)
Just by entering, you’ll be awash in Villa D’ Citta’s exquisite yet intimate atmosphere, exemplified by the warm interior lights and plush vintage furniture. The same can be said of their special suites in that they differ in configuration but still deliver a romantic ambiance. Start the morning with an alfresco breakfast on the balcony, and snuggle up by the fireplace to ward off the cold come nighttime.
Mangia, the hotel’s restaurant, offers Italian delights and favorites such as pizza, frittata, and a complimentary glass of Capriccio wine. You can also order a bottle of Capriccio and enjoy it together while soaking in the hot tub on the sun deck.
Villa D' Citta
Address: 2230 N Halsted Street
4.98 km (3.1 mi) from Millennium Park
2. Swissotel - Chicago (from USD 225)
Swissotel - Chicago offers beautiful accommodations in classy modern designs with amazing views of the city skyline and Lake Michigan. With its lakeside location, couples can enjoy activities such as cruises, walks at the park, and even some fishing.
Spend a day with your partner at this hotel with a spa, whose menu includes treatments such as shea butter body quenches and hot stone massages. Afterward, try some huge Nova Scotia lobsters at The Palm restaurant and grab a couple’s cocktail at the Amuse bar.
Swissotel Chicago
Address: 323 East Wacker Drive
584 meters (0.4 ft) from Millennium Park
Top guest reviews
Cleanliness:
the hotel was very cleanRead more reviewsHost:
the staff were helpful and respectfulnice locationvalet staff is very friendly but signage needs some workthe palm and staff were fantasticextremely friendly staff remembering us from previous visitsEarn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.
3. theWit Chicago (from USD 186)
Just a short walk from Millennium Park, The Art Institute of Chicago, and Cloud Gate is the stylish theWit Chicago. Its close proximity to the nightlife district makes it a popular choice among travelers, especially young adults.
Couples also prefer to stay here because of its world-class spa and sauna facilities, which takes romantic staycations up a few notches. Surprise your loved one with a few nights at the luxury spa suite that has a spacious bathtub and a private balcony.
theWit Chicago, a Hilton Hotel
Address: 201 N State Street
579 meters (0.4 ft) from Millennium Park
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.
4. The Langham Chicago (from USD 475)
The 5-star stature of The Langham Chicago is a hint that it’s one of the best places for a staycation in Chicago. Guests staying at the property have everything they need for a romantic getaway, from a secluded location and a lovely terrace to great amenities and stunning surroundings.
The accommodation features air conditioning, flat-screen television, and free parking, but also a fully equipped kitchen for guests looking to cook dinner themselves. Couples staying here can dine on the terrace, sit back and relax, or take the more adventurous road and go hiking or golfing.
The Langham Chicago
Address: 330 North Wabash Avenue
774 meters (0.5 ft) from Millennium Park
5. The Peninsula Chicago (from USD 427)
Travelers looking for a romantic getaway to the Windy City will find the top-notch services, modern amenities, and luxury decor they want to surprise their loved one with at the five-star Peninsula Hotel. Home to award-winning restaurants, an Asian-inspired spa, and an indoor pool with floor-to-ceiling windows overlooking the city, the hotel guarantees to delight even the pickiest guests. The luxurious rooms feature a temperature and light control console, an ensuite bathroom with a soaking tub, flat-screen television, and free Wi-Fi. Come evening, guests can enjoy a glass of champagne and chocolate, or they can have a drink at the hotel bar.
The Peninsula Chicago
Address: 108 East Superior Street
1.48 km (1.0 mi) from Millennium Park
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.
6. Viceroy Chicago (from USD 465)
The 5-star Viceroy Hotel is one of the best romantic hotels in Chicago, as it features a long list of great amenities, has an excellent location, and modern, spacious rooms. The hotel is steps from a lively dining and shopping scene but offers plenty to do on-site too. The hotel comes with a rooftop bar where guests can sip cocktails and take in the city skyline views, a seasonal rooftop pool, a restaurant, and a great fitness center.
The luxurious rooms boast a lounge area, free Wi-Fi, flat-screen television, a minibar, and a coffeemaker. The ensuite bathroom features either a bathtub or a rainfall shower, a large makeup mirror, and upscale toiletries.
Viceroy Chicago
Address: 1118 North State Street
2.27 km (1.5 mi) from Millennium Park
7. Waldorf Astoria Chicago (from USD 575)
Another excellent Chicago romantic staycation idea that’s valued by many couples in search of an exquisite experience is the Waldorf Astoria. The hotel is located in the Gold Coast neighborhood, next to shopping and dining options galore. The list of on-site amenities and facilities is quite long, as the hotel has a spa and wellness center, a restaurant, an indoor pool, and a fitness center. Rooms at Waldorf Astoria come with comfortable beds, a refrigerator, and a microwave, flat-screen television, an ensuite bathroom with a soaking tub, and some rooms even have a fireplace or a sofa bed.
Waldorf Astoria Chicago
Address: 11 East Walton
1.96 km (1.3 mi) from Millennium Park
8. Trump International Hotel & Tower Chicago (from USD 356)
The tall and imposing Trump International Hotel is among the favorite luxury picks for couples looking for a relaxing, romantic stay. The hotel pampers its guests with luxury spa services, upscale fine dining options, pool access, and epic views from every part of the hotel. Rooms are spacious and boast floor-to-ceiling windows overlooking Lake Michigan or the Chicago skyline. Some of the in-room amenities include air conditioning, a coffeemaker, flat-screen television, an iPod dock, and a private bathroom with a soaking bathtub and complimentary toiletries.
Trump International Hotel & Tower Chicago
Address: 401 N Wabash Ave
769 meters (0.5 ft) from Millennium Park
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.
9. Park Hyatt Chicago (from USD 465)
Romance has never felt as good as it does at the Park Hyatt Chicago, and it’s not just us saying it. Couples who have previously stayed here loved the salon and spa services, the indoor pool, as well as the luxury rooms with comfortable beds. Every room in the hotel also features an iPod dock, flat-screen television, and a minibar, as well as a private bathroom with a bathtub, robes, towels, and complimentary toiletries.
Come morning, guests can savor an American breakfast with international influences and great coffee. Casual dining options and drinks are also available, out on the terrace.
Park Hyatt Chicago
Address: 800 North Michigan Avenue
1.61 km (1.0 mi) from Millennium Park
10. The Palmer House Hilton (from USD 211)
The Palmer House Hilton on East Monroe Street is one of the most stylish stays in Chicago. This staycation hotel is ideal for all guests, especially couples, who plan to explore the theater district of Chicago. To make your stay extra convenient, a fully-equipped spa and wellness center, as well as a world-class gym, are available on the property.
For a much more romantic experience, book a premier suite that features a bathtub. Bathing with your partner has never been this luxurious!
The Palmer House Hilton
Address: 17 East Monroe Street
424 meters (0.3 ft) from Millennium Park
11. The Hotel at Midtown (from USD 396)
One of the great staycation choices around the iconic Lincoln Park is The Hotel at Midtown, which is located along North Elston Avenue. Some of the nearby attractions include Holstein Park, Diversey River Bowl, and Quenchers. What makes this four-star accommodation an ideal choice for your upcoming romantic outing is its high-quality hot tubs, fully equipped spa, and a large outdoor pool. With the abundance of on-site restaurants and bars, you don’t have to leave the premises just to have a good time.
The Hotel at Midtown
Address: 2444 N Elston, Lincoln Park, Chicago (IL), United States, 60647
6.55 km (4.1 mi) from Millennium Park
12. Kimpton Hotel Palomar Chicago (from USD 229)
Couples who choose to stay at this four-star boutique hotel get to enjoy a central location, right in downtown Chicago, but also exceptional service and facilities. Guests can spend their time by the indoor pool, on the sundeck, or in their rooms, enjoying the hotel’s spa services. Come evening they can attend the hotel’s wine reception. Rooms here come with designer decor, flat-screen television, a fully stocked minibar, a coffeemaker, in-room dining services, and a large bathroom with animal-print bathrobes and complimentary toiletries. The tall windows offer guests views of the city or the patio.
The Royal Sonesta Chicago River North
Address: 505 North State Street
1.06 km (0.7 mi) from Millennium Park
13. Fairmont Chicago Millennium Park (from USD 309)
Located in downtown Chicago, a few minutes away from Millennium Park, this four-star Fairmont Hotel is all about luxury, comfort, and guests’ happiness. Rooms here are modern and spacious and come with a flat-screen television, a coffeemaker, a minibar, and an ensuite bathroom with a rain shower, a bathtub, and complimentary toiletries.
Couples love staying here as they can enjoy tasty cocktails and a wide selection of wines at the bar, the location is ideal for city exploring, and there is a spa, a fitness center, and a restaurant on site. All these idyllic amenities easily make the property one of the best hotels for a staycation in Chicago.
Fairmont Chicago Millennium Park
Address: 200 North Columbus
438 meters (0.3 ft) from Millennium Park
14. Loews Chicago Hotel (from USD 299)
The modern Loews Hotel is a striking appearance on the Chicago skyline, as it stands tall near the Chicago River. Aside from the excellent Chicago romantic staycation packages, couples love coming here for the state-of-the-art facilities, including a rooftop lounge, a modern restaurant, an indoor pool, and an on-site spa. Each room offers city or lake views and features an iPod dock, flat-screen television, a minibar, a coffeemaker, but also luxury bedding, and a deluxe bathroom with a walk-in shower, complimentary toiletries, high-quality towels, and comfortable robes.
Loews Chicago Hotel
Address: 455 North Park Drive
882 meters (0.6 ft) from Millennium Park
Romance has never looked better than at these spectacular Chicago hotels
These accommodations sure know how to offer lovebirds an unforgettable experience. Everything from the luxury bathrooms, epic views, and top-quality beds to the spa services and dining experiences entice the senses. If you’re planning a romantic getaway to Chicago, these staycation hotels for couples are great hideaways to spend quality time with your partner.
Frequently asked questions about romantic staycations in Chicago
History
Get Trip101 in your inbox
Unsubscribe in one click. See our Privacy Policy for more information on how we use your data
-
10 Best Hotels With Rooftop Pools in Chicago, ILChia Han Keong -
-
-
-
-
-
-
-
-
-
Create an account to