Beautiful Chicago skyline aerial drone view from above the frozen ice and snow covering Lake Michigan with a curved hooked pier near Montrose beach with colorful orange and pink sunset clouds above.

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Our top choices for Uptown hotels

The Guesthouse Hotel

The Guesthouse Hotel
4.0 star property
Uptown
9.8 out of 10, Exceptional, (401 reviews)
"We stay here every time we come to Chicago. Great location, excellent rooms, the staff really make you feel at home. I wouldn’t ever consider staying anywhere else!"
United States
Edward
The price is £327
includes taxes & fees
30 Jun - 1 Jul
The Guesthouse Hotel

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Streeterville, 5.7 mi from Uptown
9.4 out of 10, Exceptional, (2,537 reviews)
"Great views of the lake, staff very helpful the rooms were clean and comfortable. Would stay there again!"
United States
Deborah
The price is £217
includes taxes & fees
30 Jun - 1 Jul
Sable at Navy Pier Chicago, Curio Collection by Hilton

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Theatre District, 6 mi from Uptown
9.2 out of 10, Wonderful, (2,243 reviews)
"Great location"
United States
Gabino
The price is £137
includes taxes & fees
5 Jul - 6 Jul
Silversmith Hotel Chicago Downtown

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 6.4 mi from Uptown
8.0 out of 10, Very good, (10,244 reviews)
"Great stay thanks"
United States
Felipa
The price is £121
includes taxes & fees
29 Jun - 30 Jun
Congress Plaza Hotel

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Streeterville, 4.8 mi from Uptown
9.0 out of 10, Wonderful, (4,403 reviews)
"Great stay!"
United States
Avradita
The price is £139
includes taxes & fees
2 Jul - 3 Jul
Hilton Chicago/Magnificent Mile Suites

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
River North, 5.1 mi from Uptown
9.0 out of 10, Wonderful, (3,635 reviews)
"Had an amazing stay here!"
United States
Audrey
The price is £142
includes taxes & fees
1 Jul - 2 Jul
Eurostars Magnificent Mile

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Theatre District, 5.9 mi from Uptown
9.4 out of 10, Exceptional, (1,088 reviews)
"Such a lovely hotel with a beautiful, excellent staff, and lots of character!"
United States
Debby
The price is £146
includes taxes & fees
6 Jul - 7 Jul
Staypineapple, An Iconic Hotel, The Loop

Freehand Chicago

Freehand Chicago
4.0 star property
River North, 5.3 mi from Uptown
8.0 out of 10, Very good, (3,094 reviews)
"Staff very easy to talk with and happy to help Useful amenities, location was even better than anticipated."
United States
John
The price is £139
includes taxes & fees
5 Jul - 6 Jul
Freehand Chicago

Omni Chicago Hotel

Omni Chicago Hotel
4.5 star property
Streeterville, 5.1 mi from Uptown
9.2 out of 10, Wonderful, (1,801 reviews)
"All around great property and a wonderful location"
United States
Bruce
The price is £142
includes taxes & fees
30 Jun - 1 Jul
Omni Chicago Hotel

Best Western Grant Park Hotel

Best Western Grant Park Hotel
2.5 star property
The Loop, 6.8 mi from Uptown
8.2 out of 10, Very good, (2,723 reviews)
"Clean, working air conditioner, and great staff. Very good location as well."
United States
Alexandra
The price is £106
includes taxes & fees
1 Jul - 2 Jul
Best Western Grant Park Hotel

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
4.0 star property
Gold Coast, 4.3 mi from Uptown
8.2 out of 10, Very good, (1,581 reviews)
"Very good location, breakfast is fantastic, dinner and bar are great."
United States
Zhiwen
The price is £139
includes taxes & fees
2 Jul - 3 Jul
The Chicago Hotel Collection Ambassador Gold Coast

Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
2.0 star property
The Loop, 6.5 mi from Uptown
7.4 out of 10, Good, (2,627 reviews)
"Great location and helpful staff."
United States
Ming
The price is £120
includes taxes & fees
1 Jul - 2 Jul
Travelodge by Wyndham Downtown Chicago

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 5.2 mi from Uptown
9.4 out of 10, Exceptional, (4,410 reviews)
"The breakfast, location, and staff were amazing."
United States
Corey
The price is £164
includes taxes & fees
30 Jun - 1 Jul
Hotel Riu Plaza Chicago

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
The Loop, 5.6 mi from Uptown
9.4 out of 10, Exceptional, (3,731 reviews)
"Great location, excellent room and amenities proactively attentive staff."
United States
Robert
The price is £217
includes taxes & fees
1 Jul - 2 Jul
LondonHouse Chicago, Curio Collection by Hilton

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 6.6 mi from Uptown
8.6 out of 10, Excellent, (2,850 reviews)
"great hotel and excellent to stay"
United States
Ruben
The price is £196
includes taxes & fees
2 Jul - 3 Jul
Hilton Chicago

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Streeterville, 5.1 mi from Uptown
8.6 out of 10, Excellent, (3,053 reviews)
"Great location, historic charm, friendly and helpful staff."
United States
Peter Anthony
The price is £154
includes taxes & fees
1 Jul - 2 Jul
Warwick Allerton - Chicago

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 5.6 mi from Uptown
9.4 out of 10, Exceptional, (3,508 reviews)
"Staff was great."
United States
Marianne
The price is £207
includes taxes & fees
5 Jul - 6 Jul
Hyatt Regency Chicago

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection
3.5 star property
Streeterville, 4.8 mi from Uptown
8.4 out of 10, Very good, (3,937 reviews)
"Overall a great stay, staff was friendly and bed was comfy."
United States
Meghan
The price is £124
includes taxes & fees
30 Jun - 1 Jul
The Whitehall Hotel, BW Premier Collection

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
4.0 star property
The Loop, 6.4 mi from Uptown
9.6 out of 10, Exceptional, (1,254 reviews)
"Overall comfortable stay and easy access by walk to downtown and all other places in the city."
United States
raghu
The price is £149
includes taxes & fees
5 Jul - 6 Jul
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Streeterville, 5.6 mi from Uptown
8.6 out of 10, Excellent, (1,656 reviews)
"Excellent location."
United States
Mirna
The price is £204
includes taxes & fees
2 Jul - 3 Jul
Sheraton Grand Chicago Riverwalk
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Where to stay in Uptown

Find the best Uptown areas for the activities you enjoy most.

Downtown Chicago

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Magnificent Mile

Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.

The Loop

Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.

River North

Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.

Lincoln Park

Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

Top Uptown Hotel Reviews

Find out more about Uptown

Top reasons to visit Uptown

  • Vibrant Cultural Scene: Uptown boasts a rich tapestry of cultural experiences, including local art, music, and theatre, perfect for culture enthusiasts.
  • Scenic Lakefront: Enjoy stunning views and recreational activities along the picturesque Lake Michigan, ideal for relaxation and family fun.
  • Historic Architecture: Discover Uptown's unique architectural gems and notable landmarks that reflect its rich history.
  • Diverse Accommodations: A variety of lodging options cater to all visitors, including pet-friendly hotels and family-oriented facilities.
  • Family-Friendly Activities: With plenty of attractions and activities, Uptown is perfect for a memorable family holiday.

Find great hotels near Uptown

Uptown, Chicago, offers a diverse selection of accommodations, ranging from stylish hotels to comfortable apartment blocks, catering to both leisure and business travellers. Many establishments provide pet-friendly options and excellent amenities for family vacations. With the iconic Uptown Theatre nearby and beautiful lakefront attractions, you'll find a perfect blend of relaxation and entertainment. Whether you prefer a main floor room or a nearby motel, Uptown has something to satisfy every visitor's needs.

  • The Whitehall Hotel, BW Premier Collection: Nestled in a vibrant shopping district, The Whitehall Hotel, BW Premier Collection is a charming 4-star boutique hotel with a guest rating of 8.4. Ideal for travellers seeking a unique experience, this hotel features eclectic decor and artistic touches that create a welcoming atmosphere. The property is pet-friendly, allowing dogs and providing amenities such as specified pet policies and deposits. With its proximity to local shops, guests can indulge in a delightful shopping spree before retreating to the comfort of their stylishly designed rooms.
  • Warwick Allerton - Chicago: Offering a family-friendly environment, Warwick Allerton - Chicago is a sophisticated 4-star hotel rated at 8.6. Situated 8.0km from Uptown, this property caters to families and business travellers alike with thoughtful amenities for children, including travel cribs and babysitting services. Its elegant design and convenient location make it a perfect base for exploring the city, while guests can enjoy a relaxing atmosphere that combines modern comfort with traditional charm.
  • Embassy Suites by Hilton Chicago Downtown River North: This 4-star hotel, also rated at 8.6, provides a spacious and family-oriented environment in the heart of the city. With complimentary amenities for children and a focus on both leisure and business travellers, Embassy Suites by Hilton Chicago Downtown River North is an excellent choice for those looking to explore vibrant city life. Guests can relax in generous suites and enjoy the convenience of being close to numerous attractions, making it an ideal spot for memorable family adventures.

Where to stay near Uptown

Uptown, Chicago, offers a delightful blend of family-friendly activities and cultural experiences. From its vibrant streets adorned with local art to the scenic views of nearby Lake Michigan, there's something for everyone. Explore the charming Uptown neighbourhood, or venture into downtown Chicago for urban excitement. With its welcoming atmosphere and friendly locals, your visit promises a memorable journey full of culture and adventure in this dynamic area.

  • Chicago: As a bustling metropolis, Chicago is a vibrant hub that offers an array of experiences for visitors. Uptown, located within Chicago, is a diverse area rich in culture and entertainment. The city welcomes tourists year-round, with peak visitor numbers during the summer months. Chicago is famous for its shopping districts, arena entertainment facilities, and a thriving theatre scene. Notable landmarks include iconic sports stadiums and beautifully designed urban parks, making it an ideal destination for families and outdoor enthusiasts alike.
  • Downtown Chicago: Located a mere 9.7km from Uptown, Downtown Chicago is the city’s heartbeat, pulsating with energy and excitement. This neighbourhood attracts visitors throughout the year, with a seasonal peak in the summer. Families and outdoor lovers will find plenty to enjoy here, from expansive shopping areas to lively theatre productions. Downtown is also home to significant urban parks and sports facilities, ensuring that there's always something happening. Its central location makes it an excellent base for exploring the rest of the city.
  • Buena Park: Just 966m from Uptown, Buena Park is a charming neighbourhood that combines a family-friendly atmosphere with cultural richness. Visitors frequent the area year-round, but summer sees the highest influx. Here, you can indulge in educational experiences, enjoy local theatre, or explore bustling shopping spots. Noteworthy attractions include picturesque beaches and urban parks, perfect for a leisurely day out. Buena Park's proximity to Uptown makes it an easily accessible gem worth exploring.

Things to do near Uptown

Uptown, Chicago, offers a delightful mix of family-friendly activities and cultural experiences. Enjoy vibrant shopping, explore local attractions, and immerse yourself in the area's rich theatre and music scene. Don't miss the chance to discover art galleries and partake in city tours, making it an ideal destination for those seeking adventure and culture in a lively urban setting.

Shopping

In Uptown, you can explore the vibrant shopping scene at the historic Aragon Ballroom and nearby boutiques, offering unique gifts and souvenirs. Don't miss the local markets, where you can find handcrafted items and local delicacies, perfect for mementoes from your visit.

Recreation

At Chevy Chase Country Club, indulge in a serene atmosphere with top-notch amenities, perfect for relaxation and leisure. Similarly, Ravinia Green Country Club offers an elegant setting for wellness activities, ensuring a rejuvenating experience amid lush landscapes and luxurious facilities.

Adventure

Explore Montrose Beach for a day of sun and sand, perfect for swimming and beach volleyball. Nearby, the Montrose Point Bird Sanctuary offers tranquil walks and birdwatching opportunities in a natural setting, ideal for those seeking adventure in the great outdoors.

Nightlife

Uptown Chicago offers a vibrant nightlife with a mix of trendy bars and live music venues. Enjoy a craft cocktail at the stylish Green Mill Cocktail Lounge, or experience live jazz at the iconic venue. For a more laid-back vibe, visit the local pubs along Montrose Avenue.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Uptown

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay around Uptown are December to February, where the prices are slightly lower. This is in comparison to June and September to October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay around Uptown is Monday. The most expensive day to stay around Uptown is Saturday.
  • Find cheap hotels on Expedia: Utilise Expedia's search tool to refine your preferences, including your budget, desired location, and preferred hotel type. To discover the most affordable prices and offers, arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel booking in Uptown with your flights and activities through an Expedia package.

Find the best attractions in and around Uptown

Uptown, Chicago, is ideal for family-friendly and culture-themed holidays, offering a delightful mix of attractions. Visitors can explore beautiful beaches, stunning skyscrapers, and urban parks, making it perfect for those seeking a blend of city and beach experiences. Don't miss the opportunity to admire Uptown's unique architecture, visit its notable landmarks, and enjoy performances at the local theatres for a truly enriching getaway.

  • Montrose Beach: Experience the stunning natural beauty of Montrose Beach, where you can relax on sandy shores, enjoy beach sports, and take in scenic views of Lake Michigan. The beach vibe offers a perfect escape, whether you fancy a leisurely stroll or a sun-soaked day with friends and family.
  • Michigan Avenue: Known as the Magnificent Mile, Michigan Avenue is a bustling street that boasts high-end shopping, dining, and iconic landmarks. Immerse yourself in the vibrant city atmosphere, where modern architecture meets historical sites, providing an exciting urban experience.
  • 875 North Michigan Avenue: This striking skyscraper, formerly known as the John Hancock Center, offers breathtaking views from its observation deck. The city vibe here is electric, making it an ideal spot for photography enthusiasts and those seeking a panoramic perspective of Chicago.

Best time to go to Uptown

The best time to visit Uptown is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.7°F (-3.5°C)Light RainMostly CloudySlightly LowSlightly Low
February27.0°F (-2.8°C)Light RainMostly CloudyAverageSlightly Low
March37.0°F (2.8°C)Light RainMostly CloudyAverageAverage
April46.0°F (7.8°C)Light RainMostly SunnyAverageAverage
May57.0°F (13.9°C)Light RainMostly SunnyAverageAverage
June67.3°F (19.6°C)Light RainMostly SunnySlightly HighSlightly High
July73.4°F (23.0°C)Light RainMostly SunnySlightly HighAverage
August73.0°F (22.8°C)Light RainMostly SunnyAverageAverage
September67.1°F (19.5°C)Light RainMostly SunnySlightly HighSlightly High
October54.9°F (12.7°C)Light RainMostly SunnyAverageSlightly High
November42.3°F (5.7°C)Light RainMostly SunnySlightly LowAverage
December33.1°F (0.6°C)Light RainMostly CloudySlightly LowSlightly Low

The nearest major airports for your trip to Uptown

Accessing Uptown, Chicago, is convenient via its two major airports. Chicago O'Hare International Airport (ORD) is approximately 20.9km away and offers excellent hotel options such as the 4.5-star Loews Chicago O'Hare Hotel and the Hyatt Regency O'Hare Chicago, both just 3.2km from the airport. Chicago Midway International Airport (MDW) is also around 20.9km from Uptown, with luxurious accommodations like The Langham, Chicago and Trump International Hotel & Tower, both situated 14.5km away. For those considering South Bend International Airport (SBN), located 114.3km from Uptown, nearby hotels include the 4-star Doubletree Hotel South Bend, just 6.4km from the airport.

Frequently asked questions

What other neighbourhoods are similar to Uptown?
For visitors seeking a similar experience to Uptown, the neighbourhoods of Andersonville and Lakeview offer comparable appeal.

Andersonville, located just north of Uptown, shares a similar independent spirit and a strong sense of community. It's known for its Swedish heritage, reflected in many of its shops and restaurants along Clark Street. The area has a distinctive main street, a bit like Broadway in Uptown, with a mix of boutiques, cafes, and eateries. It's a particularly good fit for solo travellers or couples who appreciate unique, locally-owned businesses and a relaxed, friendly atmosphere.

Lakeview, situated immediately south of Uptown, provides a similar blend of residential comfort and entertainment, though often on a grander scale. Broadway runs through Lakeview as well, offering an extensive selection of shops, restaurants, and theatres. It's also home to Wrigleyville, a distinct sub-neighbourhood known for its baseball stadium, which attracts many visitors.
What are the best hotels in Uptown that travellers recommend?
For an excellent hotel in Uptown that travellers highly recommend, consider The Guesthouse Hotel.

The 4-star Guesthouse Hotel, with an outstanding 9.8 rating, is frequently praised for its amazing staff and quiet, wonderful rooms. This hotel offers premium bedding and air conditioning for a comfortable stay. Guests appreciate the convenience of an in-room kitchen and the availability of an electric car charging station and self-parking. Nearby points of interest include Lincoln Park, Challenger Park, About Face Theater, Pegasus Players, and Foster Avenue Beach.
What are the best family hotels in Uptown?
For an excellent family-friendly option in Uptown, The Guesthouse Hotel is highly recommended.

This 4-star hotel, with an outstanding 9.8 rating, is praised by guests for its quiet rooms and amazing staff. It offers convenient amenities such as free cribs, kitchens in the rooms, and an electric car charging station. It is also well-located, being just 1.7 km from Challenger Park and Foster Avenue Beach, and 0.9 km from About Face Theater.
What are the top pet-friendly hotels in Uptown?
For top pet-friendly hotels in Uptown, The Guesthouse Hotel is an excellent choice.

The 4-star Guesthouse Hotel, with a superb 9.8 rating, is highly recommended for travellers with pets. It not only permits pets but also welcomes dogs specifically, providing thoughtful amenities like food and water bowls. An added bonus is that pets stay free of charge. Guests frequently praise the amazing staff and the quiet, wonderful rooms, ensuring a comfortable stay for both you and your furry companion. The hotel is conveniently located near Challenger Park, just 1.7 km away, and Foster Avenue Beach, also 1.7 km, offering lovely spaces for walks.
When is the best time to go to Uptown?
The best time to go to Uptown is from late spring to early autumn, specifically May through September, when the weather is most pleasant for exploring.

During these months, the temperatures are generally mild to warm, making it ideal for walking along the lakefront, enjoying outdoor dining, and attending local events. You'll find plenty of sunshine and comfortable conditions for sightseeing.

For those who enjoy outdoor activities and festivals, the summer months of June, July, and August are particularly good. There are often free concerts in the parks and various community events taking place, offering a lively experience.

If you prefer slightly cooler weather and fewer crowds, late spring (May) and early autumn (September) are excellent choices.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Uptown.
How can I save on a Uptown hotel booking with Expedia?
Members always get our best prices. Find our best Uptown hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
How much is the nightly rate at a Uptown hotel?
Hotel prices in Uptown often vary, but you can find a great deal on Expedia. Different factors affect nightly hotel rates, such as the time of year or the days of the week you want to book. To find the best deals for your stay, be flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates.

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