Chicago, often called the Windy City, is a multi-layered metropolitan. There is much to experience here from sports, endless skyscrapers, the best of modern architecture, local fast-food joints, a host of Michelin-starred restaurants, famous spots like The Bean, walking trails on Lake Michigan shoreline, parks, museums, and much more. In addition, there is a festival here for everyone! Whether you like blues music or jazz, stamp collecting or world cinema, martial arts or political discourse, you’ll find an event or a festival to suit your taste. Lose yourself in the charms of the Windy City. You’ll find that it wins your heart with its underrated charm. And, to make your travel planning easier, here is a list of the top staycation spots in Chicago, Illinois.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on April 19, 2025.
Explore more staycation options - travel within your comfort zone
If you’re looking for stays more tailored to your every need, here are some of our top recommendations:
Vacation rentals
- Bed And Breakfasts In Chicago, Illinois
- Rent A Boat In Chicago, IllinoisCouple staycations
- Best Romantic Staycations In Chicago, Illinois
- 14 Best Romantic Hotels For Couples In ChicagoFamily-friendly accommodations
- Best Chicago Hotels With Kid-Friendly Pools
- Kid-friendly Hotels In Chicago, Illinois, USAStaycation spots with popular facilities and experiences
- Hotels With Restaurant In Chicago, Illinois
- Hotels With Pools In Chicago, Illinois
- Hotels With Rooftop Bars In Chicago, Illinois
- Top Hotels With Indoor Pools In Chicago, IllinoisOther unique staycation accommodations
- Green Hotels In Chicago, Illinois
- Best Campsites In Chicago, Illinois
- Top 10 Historic Hotels In Chicago, Illinois
- Boutique Hotels In Chicago, Illinois, USA
- Best Party Hotels In Chicago, Illinois
1. Four Seasons Hotel Chicago (from USD 563)
Four Seasons hotel offers you a superb location. It is just a few steps away from Michigan Avenue’s Magnificent Mile (which offers the best luxury shopping, dining, and entertainment). The rooms here are a delight with vintage French décor, marble bathrooms with Malin + Goetz amenities, panoramic views of the Chicago skyline or Lake Michigan, a TV, free WiFi, and iHome clock radio. You can enjoy other facilities such as the restaurant, clubroom, fitness center, and the spa with a Romanesque sauna, pool, and hot tub for relaxation.
Four Seasons Chicago
1.88 km (1.2 mi) from Millennium Park
2. Trump International Hotel & Tower Chicago (from USD 391)
Located above the Loop and North Michigan Avenue along the Chicago River, this beautiful hotel is one of the most highly rated accommodations in Booking.com. Every room comes with floor-to-ceiling windows ensuring you have a stunning view of Lake Michigan, Chicago River, or the city skyline. Rooms are luxuriously furnished; guests love the limestone bathroom with a deep soaking bathtub. You’ll also have access to a large heated indoor swimming pool. There are plenty of restaurants, shopping, and food options nearby for you to explore.
Trump International Hotel & Tower Chicago
769 meters (0.5 ft) from Millennium Park
3. Sofitel Chicago Water Tower (from USD 298)
Sofitel Chicago is the quintessential luxury Chicago Gold Coast hotel. You get to enjoy views of Lake Michigan and the city skyline from this 32-floor prism glass building. The French Art De Vivre decor rooms feature luxury feathertop duvet bedding, a spacious marble bathroom, free WiFi, and a mini bar. Other facilities include a ballroom, a fitness center, parking, and airport shuttle facilities. The Navy Pier and the Art Institute of Chicago are 3.2 km (1.9 miles) from here.
Sofitel Chicago Magnificent Mile This is a Proud Certified property where you can be extra sure of a welcoming stay.
1.83 km (1.2 mi) from Millennium Park
4. The Peninsula Chicago (from USD 587)
Located just a five-minute walk from the Museum of Contemporary Art, this hotel boasts award-winning restaurants, a modern gym with fitness and yoga classes, and an Asian-inspired spa. You’ll enjoy the spacious luxury guest rooms with city views. All rooms have a TV, free WiFi, temperature and lighting control console, and an en-suite bathroom with a bathtub. The afternoon tea with champagne and chocolate are a must try here. In the evenings, walk across the street to enjoy the historic Water Tower Place.
The Peninsula Chicago
1.51 km (1.0 mi) from Millennium Park
5. Conrad Chicago (from USD 332)
Conrad Chicago, located just 300 m (984 feet) from Michigan Avenue, is the perfect place for business travelers and families. They have a business center and a 24-hour front desk with staff who speak English and Spanish. They offer comfortable rooms, free American breakfast, bottled water in the room, parking, family rooms, non-smoking rooms, a restaurant, and the rooms are pet-friendly as well. You’ll have shopping options nearby as well, including Magnificent Mile and Water Tower Place which feature all the popular brands.
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
Address: 521 North Rush Street, River North, Chicago (IL), United States, 60611
1.04 km (0.7 mi) from Millennium Park
6. The Langham, Chicago (from USD 587)
This upscale luxury hotel towers above the city and offers guests some stunning views. It is conveniently located in the heart of downtown Chicago. Their rooms are done up in warm tones and dark wood accents. You can try some traditional-Chinese-medicine-inspired treatments at Chuan Spa, their award-winning wellness retreat. Other facilities include a traveler kitchen, a bar, a lounge, Afternoon Tea with Wedgwood, in-room dining services, and a state-of-the-art fitness studio.
The Langham Chicago
774 meters (0.5 ft) from Millennium Park
7. The Ritz-Carlton Chicago - A Four Seasons Hotel (from USD 480)
The Ritz-Carlton, located atop Water Tower Place, is an oasis of comfort. It offers impeccable service, beautifully decorated rooms with unparalleled views, marble bathrooms with free deluxe toiletries, and a host of facilities for guests to enjoy. Start your days with an invigorating swim in their temperature-controlled, four-lane lap pool. You can easily walk to attractions such as Michigan Avenue, Navy Pier, Art Institute of Chicago, Arts Club of Chicago, Chicago Museum of Contemporary Art, and Loyola University Museum of Art.
The Ritz-Carlton, Chicago
1.7 km (1.1 mi) from Millennium Park
8. Park Hyatt - Chicago (from USD 565)
Just across the street from the historic Water Tower, this luxury hotel boasts of a great location and services. They have a world-renowned on-site spa and restaurant, complimentary bike rental service, a fitness center, and drinks and casual dining options on an outdoor terrace. You can walk to the Oak Street Beach at Lake Michigan and the Navy Pier within 10 minutes. You also have the Hyatt e-Concierge service to book appointments from your room.
Park Hyatt Chicago
1.61 km (1.0 mi) from Millennium Park
9. Viceroy Chicago (from USD 432)
If you like hotels with a modern vibe, then you’ll enjoy a stay at Viceroy Chicago. Their chic guest rooms offer all comforts including cable TV, plush lounge seating, free WiFi, a well-stocked minibar, and a coffee machine. Spend your evening enjoying the view from the rooftop bar and lounge while sipping a crafted cocktail. The on-site restaurant offers dishes with modern, Midwest flavors.
Viceroy Chicago This is a Proud Certified property where you can be extra sure of a welcoming stay.
2.29 km (1.5 mi) from Millennium Park
10. JW Marriott Chicago (from USD 603)
To experience a slice of Chicago history, stay at the JW Marriott. This Chicago Loop hotel is famous for its architectural design. The rooms are comfortably furnished and stocked with all amenities. In addition, you have access to a host of on-site facilities and dining options. You can walk to the Millennium Park and the Art Institute Museum from here. You can easily travel to Chicago’s most popular attractions through the Monroe Public Transit stop, which is just three blocks away. It is perfect if you love parks, architecture, and museums.
JW Marriott Chicago This is a Proud Certified property where you can be extra sure of a welcoming stay.
948 meters (0.6 ft) from Millennium Park
Chicago: soulful and strong
Barack Obama once said, “Let me tell you something. I’m from Chicago. I don’t break.” This quotes beautifully sums up the incredible spirit of this fascinating American city. So for your next holiday, book a stay in one of the best Chicago hotels and experience it the right way. You’ll leave with your very own Windy City stories and songs!
History
Get Trip101 in your inbox
Unsubscribe in one click. See our Privacy Policy for more information on how we use your data
