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With so much to see and do close to home, Chicago is one of the best cities in America to plan a staycation. Better yet, there are lots of great hotels, Airbnbs, and VRBO properties to call your home base as you get to know your area. Here are our top staycation recommendations in Chicago!


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52nd Floor MagMile Penthouse
Credit: VRBO.com

52nd Floor MagMile Penthouse

It doesn’t get much better for a Chicago staycation than this penthouse with a fireplace, fitness center, pool, and Wi-Fi. This is a one-bedroom, one-bath luxury condo that sleeps two to four people and measures 1,050 square feet. You’ll love the Lake Michigan views here and being close to both North Michigan Avenue and the River North District. Children are welcome at this property, which has a washer and dryer, parking for a daily fee, and bathroom and kitchen stocked with everything you need.

The Gwen The Gwen, A Luxury Collection Hotel, Michigan Avenue Chicago
Credit: marriott.com
The Gwen, A Luxury Collection Hotel, Michigan Avenue Chicago

The Gwen

Choose The Gwen for your staycation and you’ll enjoy a fun 1930s style with all the 21st-century amenities you could hope for. The hotel is in the McGraw-Hill Building on the Magnificent Mile and home to the Kostali restaurant with its amazing Mediterranean dinner menu. For your staycation, you’ll get access to the 24-hour fitness center, complimentary use of bicycles, a seasonal outdoor lounge and terrace, laundry service, Wi-Fi, and mixology services. The guest rooms range from 375 to 425 square feet, but there are also suites between 475 and 3,000 square feet to give you some extra room for a longer stay or just for something special.

Apartment with Amazing Garden Space Apartment with Amazing Garden Space
Credit: airbnb.com
Apartment with Amazing Garden Space

Apartment with Amazing Garden Space

This is one of the most popular Airbnb properties in Chicago and a top pick for a staycation close to home. It’s an apartment that accommodates up to five guests in two bedrooms and one bath. The host offers the highest cleanliness standards, as well as an outdoor deck, garden space, and workspace so you can work from your “home on the road.” The apartment is in Logan Square and in walking distance to bars and restaurants. It’s by the blue line for easy public transportation, has lots of free street parking, and is a brick two-flat where the host lives upstairs in a separate unit. It’s a fully private space with bike storage, a full kitchen, Wi-Fi, and lots of family-friendly amenities that include a pack-and-play and high chair.

Peninsula Chicago Peninsula Chicago
Credit: peninsula.com
Peninsula Chicago

Peninsula Chicago

A top spa hotel in Chicago, The Peninsula is a 5-star hotel in downtown Chicago that is a top luxury pick for a local staycation. The hotel offers luxurious room accommodations and is home to Z Bar, a lovely rooftop lounge with epic views. Pamper yourself with a spa treatment here on the 19th and 20th floors where a lovely in-house spa is located. There’s a fitness center here with views of the city skyline and an adjoining indoor half-Olympic-size swimming pool. Chicago residents can get a membership at the spa and fitness center and have access and discounts on group fitness classes, personal training sessions, and more wellness perks.

Industrial Style Chicago Loft Living room at Industrial Style Chicago Loft with Free Parking
Credit: airbnb.com
Living room at Industrial Style Chicago Loft with Free Parking

Industrial Style Chicago Loft

A popular Airbnb property for your staycation is this loft that you’ll have all to yourselves. It is great for two guests and has one bedroom and one bath. The space has a chic, industrial vibe and features a private outdoor deck, exposed brick walls, and free parking. Guests also can use the full-size refrigerator, stainless steel appliances, dining table, and basic cooking supplies. When you stay here, you’ll be about 10 minutes from Wrigley Field and a 20-minute drive to the downtown attractions and airport. For this staycation spot, you receive a private entry code before your stay for easy check-in and check-out. Courtesy luggage drop-off and storage is available at the restaurant downstairs.

The Ritz-Carlton Chicago Sitting area at The Ritz-Carlton Chicago
Credit: ritzcarlton.com
Sitting area at The Ritz-Carlton Chicago

The Ritz-Carlton Chicago

The Ritz-Carlton Chicago is a popular family staycation destination that’s close to Lake Michigan and has lots of hotel amenities. It’s at Water Tower Place and has an extended fitness center. In addition to rooms and suites, you can stay for a little longer in a one-bedroom or two-bedroom apartment and truly feel like you’re in a home away from home. The hotel has its own spa with membership options that include access to the pool and fitness center. On-site dining options include an Italian steakhouse, café, bar, and rooftop area.

Kimpton Hotel Palomar Chicago Kimpton Hotel Palomar Chicago
Kimpton Hotel Palomar Chicago

Kimpton Hotel Palomar Chicago

To be in the stylish River North area of Chicago for your staycation, consider the Kimpton Hotel Palomar Chicago. This lifestyle boutique hotel has a pool on the 17th floor, Sable Kitchen & Bar for local flavors, and wellness programs that go beyond just a standard gym. When you take your vacation close to home here, you’ll have access to complimentary PUBLIC bikes, spa treatments, daily wine hour, and lovely city views. Bring your pup with you because there are pet-friendly rooms at the Kimpton.

Bella Villa on Taylor Street Bella Villa on Taylor Street
Credit: VRBO.com
Bella Villa on Taylor Street

Bella Villa on Taylor Street

When you book this staycation destination, you’ll be in Chicago’s Little Italy and just a mile west of the Loop and UIC. It’s a three-bedroom, two-bathroom apartment on Little Italy’s restaurant row and a second-floor walk-up flat overlooking Taylor Street. Here you’ll be in a community with lots of trees, churches, and schools in addition to lots of great restaurants. Children are welcome here, there’s a washer and dryer, and street parking passes are available. The kitchen is well-appointed for staycations, and long-term renters are welcome.

Four Seasons Chicago Four Seasons Hotel Chicago
Credit: fourseasons.com
Four Seasons Hotel Chicago

Four Seasons Chicago

A staycation at the Four Seasons Chicago also includes high luxury features and views of the lake and skyline. This elegant and famous hotel is a foodie paradise because of James Beard Award-winning Chef Jonathon Sawyer who serves up New American cuisine onsite. The hotel also has a spa that offers many different treatments, including hydrating facials, vintage bourbon massages, couple’s treatments, nail services, and more.

Hip Chicago Apartment Hip Chicago Apartment
Credit: airbnb.com
Hip Chicago Apartment

Hip Chicago Apartment

People in Chicago love this apartment for their staycations in Logan Square because it has all the comforts of home, including a well-equipped kitchen, comfortable master bedroom, and free parking. You’ll be within walking distance of a bike rental station here, as well as the 606 Trail and lots of restaurants and bars. The unit is on the second floor and only accessible by stairs. The bathroom is equipped with everything you need, while the living room has a smart TV with free Netflix, basic cable, and high-speed internet. The entire space is professionally cleaned and sanitized after each use for your safety. Overall, it’s a great staycation pick for up to four guests in two bedrooms.

Private Pool Paradise View at Private Pool Paradise
Credit: VRBO.com
View at Private Pool Paradise

Private Pool Paradise

This VRBO property makes an excellent staycation because it’s in the heart of all the best things in Chicago and also a great place for events. The house is 1,200 square feet in size and sleeps six people with three bedrooms and one bathroom. It’s near the lakefront, downtown, Midway, McCormick Place, Soldier Field, and the museum campus. It’s in the family-friendly, safe, and centrally located McKinley Park neighborhood. The home’s pool is open from May to September, there’s free parking, and two decks to relax on. Guests can use the washer and dryer for a fee. Children are welcome here but pets are not allowed. This VRBO property practices enhanced cleaning practices for your safety too.

Park Hyatt Chicago Room at Park Hyatt Chicago
Room at Park Hyatt Chicago

Park Hyatt Chicago

The Park Hyatt Chicago offers stylish rooms and suites that will make your staycation in Chicago a special one. It’s steps from the Magnificent Mile, has an impressive private art collection, and practices extra cleaning procedures to put your wellbeing first. This is a family-friendly choice because the hotel has a kids’ camp. There’s also a fitness center, restaurant on-site, business services, spa, pool, and many other amenities. Nomi Spa at the Park Hyatt is a great place to get a massage, facial, or body therapy to feel rested and rejuvenated before you go back home. This is a pet-friendly hotel for dogs 50 pounds or lighter with a $100 fee for one to six nights.

Luxury Chicago Loft Design at Luxury Chicago Loft
Credit: airbnb.com
Design at Luxury Chicago Loft

Luxury Chicago Loft

You’ll also being in this loft space for your Chicago staycation, which you’ll have all to yourself in Wrigleyville. It’s a block from public transportation and in a very safe, family-friendly neighborhood. You’ll also be three blocks from Wrigley Field to catch a baseball game here. This is an ideal spot to experience Chicago like a local. It works well for up to four guests, has two bedrooms and two baths, and comes with two parking spots. Families with kids enjoy staying here because of the family-friendly features, including a pack-and-play and baby bath.

Waldorf Astoria Chicago Waldorf Astoria Chicago
Waldorf Astoria Chicago

Waldorf Astoria Chicago

Waldorf Astoria Chicago makes a wonderful staycation if you’re looking to treat yourself. It has a pool, fitness center, onsite dining, and spa that offers in-room treatments as well. You’ll love the indoor lap pool, the luxurious facilities and package offerings at the spa, and the two Michael Mina restaurants here. For dining, you can enjoy a classic French patisserie and a Parisian café for elevated French cuisine. Guests who stay here have access to a complimentary drop-off service in the luxury house car within a two-mile radius, business center, valet parking, laundry and dry-cleaning services, and complimentary Wi-Fi throughout the hotel.

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