Chicago Holiday Rentals, Illinois: Private House Rentals

Our top choices for Chicago hotels

River Hotel

Downtown Chicago

Enjoy riverside leisure just steps from Michigan Avenue and Chicago Riverwalk.

Ian

฿2,550 total

includes taxes & fees

1 Mar - 2 Mar

Aloft Chicago Mag Mile

Downtown Chicago

Stylish hotel near Michigan Ave with an indoor pool and American dining options.

Pablo

฿3,338 total

includes taxes & fees

22 Feb - 23 Feb

Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

Jennifer

฿2,948 total

includes taxes & fees

8 Feb - 9 Feb

Hyatt Centric The Loop Chicago

Downtown Chicago

Discover city centre luxury steps from Millennium Park and Chicago Riverwalk.

Luzabeth

฿4,269 total

includes taxes & fees

27 Feb - 28 Feb

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Downtown Chicago

Discover a serene retreat steps from Chicago's iconic Millennium Park.

Raju

฿3,388 total

includes taxes & fees

12 Feb - 13 Feb

Hyatt Regency Chicago

Downtown Chicago

Centrally located hotel with stunning city and lake views only steps from Michigan Avenue.

Tiffany

฿6,677 total

includes taxes & fees

15 Feb - 16 Feb

Eurostars Magnificent Mile

Downtown Chicago

Explore Michigan Avenue just minutes away with easy access to Chicago's finest.

Maria Rochelle

฿3,159 total

includes taxes & fees

1 Mar - 2 Mar

The Chicago Hotel Collection Ambassador Gold Coast

Downtown Chicago

Experience lakeside elegance with easy access to Michigan Avenue and Oak Street Beach.

Dhruv

฿3,653 total

includes taxes & fees

10 Feb - 11 Feb

Arlo Chicago

Downtown Chicago

Stay steps from Chicago's Millennium Park and Michigan Avenue at this prime hotel.

Jennifer

฿4,736 total

includes taxes & fees

24 Feb - 25 Feb

citizenM Chicago Downtown

Downtown Chicago

Modern hotel in city centre Chicago with 24-hour dining and stylish accommodation.

Lucie Saint Jean

฿3,779 total

includes taxes & fees

4 Feb - 5 Feb

2 restaurants, breakfast, lunch, dinner served; American cuisine

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

Enjoy the riverside elegance of city centre Chicago, steps from Michigan Avenue.

Kiran

฿5,686 total

includes taxes & fees

8 Feb - 9 Feb

Staypineapple, An Iconic Hotel, The Loop

Downtown Chicago

Lori

฿4,176 total

includes taxes & fees

12 Feb - 13 Feb

Palmer House a Hilton Hotel

Downtown Chicago

Experience Chicago's grand history at this landmark hotel steps from Millennium Park.

Melani

฿5,715 total

includes taxes & fees

21 Feb - 22 Feb

DoubleTree by Hilton Chicago - Magnificent Mile

Downtown Chicago

Enjoy a rooftop pool oasis steps from Michigan Avenue and Chicago's attractions.

Anani

฿3,129 total

includes taxes & fees

5 Feb - 6 Feb

The Royal Sonesta Chicago Downtown

Downtown Chicago

Scenic Chicago retreat steps from Riverwalk with city views and dining options.

Beryl Ivonne

฿5,896 total

includes taxes & fees

7 Feb - 8 Feb

Club Quarters Hotel Wacker at Michigan, Chicago

Downtown Chicago

Enjoy riverfront access and Chicago Theatre just steps away at this city centre hotel.

Nicholas

฿2,984 total

includes taxes & fees

12 Feb - 13 Feb

Hotel Riu Plaza Chicago

Downtown Chicago

Brisa

฿4,885 total

includes taxes & fees

9 Feb - 10 Feb

La Quinta Inn & Suites by Wyndham Chicago Downtown

Downtown Chicago

Explore Chicago's prime location within steps of Willis Tower and State Street.

Aimée

฿3,625 total

includes taxes & fees

7 Feb - 8 Feb

55-inch LCD TV with cable channels, TV, pay films

L7 Chicago by LOTTE

Downtown Chicago

Experience city centre Chicago with riverfront views and Korean cuisine on-site.

Patrick

฿5,449 total

includes taxes & fees

12 Feb - 13 Feb

Thompson Chicago, by Hyatt

Downtown Chicago

Experience Chicago in Gold Coast, near Michigan Avenue and Lake Michigan shores.

Loan

฿5,874 total

includes taxes & fees

1 Mar - 2 Mar

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Where to stay in Chicago

Find the best Chicago areas for the activities you enjoy most. Learn more about Chicago

The Loop

The Loop pulses with energy as Chicago's iconic skyline reaches skyward. Art and business collide at every corner, from Cloud Gate's gleaming curves to historic skyscrapers. Experience world-class culture at the Art Institute or Chicago Symphony Orchestra. Named for the elevated train tracks encircling city centre, this area offers excellent transit connections. Millennium Park provides green space amid urban intensity. Weekdays buzz with business crowds while weekends reveal a quieter side of this architectural wonderland.

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River North

River North captivates visitors with America's largest concentration of art galleries outside Manhattan. This upscale Chicago area blends high-end dining with vibrant nightlife along the scenic riverfront. Stunning architecture frames the bustling streets. The area boasts exceptional transit options with three nearby metro stations. Browse through contemporary exhibits, enjoy cocktails at stylish rooftop bars, or shop at luxury boutiques. Merchandise Mart and Bally's Casino offer additional entertainment in this walker-friendly urban playground.

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Magnificent Mile

Chicago's famous Magnificent Mile dazzles with luxury shopping and architectural wonders. Michigan Avenue showcases high-end retailers like Bloomingdale's and Neiman Marcus alongside historic landmarks such as the Water Tower. The district seamlessly blends shopping paradise with cultural attractions. Business travellers appreciate the numerous office buildings and hotels lining North Michigan Avenue. Visitors can enjoy fine dining establishments, explore the Chicago Riverwalk, or venture to nearby attractions like Navy Pier and the Art Institute of Chicago. The area's stunning skyline views and riverfront access create an unforgettable urban experience.

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West Loop

West Loop has transformed from industrial roots into Chicago's trendiest food destination. Old warehouses now house sleek restaurants along "Restaurant Row" where celebrity chefs create culinary magic. Art galleries and design studios fill converted brick buildings throughout this vibrant area. Union Park and Mary Bartelme Park offer green retreats amid the urban landscape. Getting around is simple with multiple train stations including Racine and Clinton. The area balances its industrial heritage with modern luxury in this walkable food lover's paradise.

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Lincoln Park

Lincoln Park blends urban energy with natural beauty along Chicago's stunning lakefront. The neighborhood's namesake 1,200-acre park offers endless recreation with a free zoo, conservatory, and scenic trails. Historic brownstones line tree-canopied streets, creating a charming residential atmosphere. Visitors can shop unique boutiques along Armitage Avenue or enjoy diverse dining options on Clark Street. The Chicago History Museum and North Avenue Beach provide cultural and outdoor attractions. Three convenient metro stations make exploring the rest of the city a breeze.

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Stay near popular Chicago attractions

Wrigley Field

4.4/5 (5,537 reviews)

Step into baseball's living museum where ivy-covered walls and a hand-operated scoreboard create timeless charm. Experience the electrifying atmosphere of Cubs games in this century-old "Friendly Confines."

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Michigan Avenue

4.6/5 (484 reviews)

Stroll down this iconic Chicago boulevard lined with luxury boutiques and historic architecture. Enjoy world-class shopping, acclaimed restaurants, or explore nearby cultural spots like the Art Institute.

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Chicago and related destinations

Towering skyscrapers frame the stunning Millennium Park where 'The Bean' reflects the city's vibrant energy. Cruise along the Chicago River for spectacular architecture views or catch a Cubs game at historic Wrigley Field.

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City of Chicago. Image of Chicago downtown and Chicago River with bridges at sunny summer day

Top Chicago Hotel Reviews

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent

"All of the above not to mention the quietness"

Eurostars Magnificent Mile

10/10 Excellent

"We arrived later than planned due to the weather, but the front desk staff greeted us warmly and made us feel welcome right away. They were very friendly and kind. As always, the room was clean this has been consistent every time we stay. The bed and pillows were comfortable, and I absolutely loved the shower. Overall, it’s an all-around great hotel, and we always enjoy our stay here."

Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent

"Super friendly staff. The included breakfast was super nice with lots of options and the evening reception was also super nice. Room was clean and nice size. Not something in their control as I think 1-2 of the elevators were out of service but the elevators took forever to come and when they did 50% of the time they were full. Waited like 10min+ every time. The design also doesn’t lend it self to being super quiet"

More cheap stays in Chicago

Motel 6 Naperville, IL

1585 Naperville Wheaton Road Naperville IL

฿1,328

฿1,480 total

15 Feb - 16 Feb

includes taxes & fees

7.8/10 Good! (1,209 reviews)

Frequently asked questions

Where is the best place to stay in Chicago?

Harvey House Bed & Breakfast is a favourite property for Expedia customers. This B&B offers free breakfast and free parking. Traveller reviews also recommend Hampton Inn & Suites Chicago Medical District UIC and The Publishing House B&B as top options for your stay. See all available top hotels, or vacation rentals in Chicago.

If I need to cancel my hotel reservation in Chicago, will I receive a refund?

Yes! You'll find that most room reservations are fully refundable provided that you cancel before the accommodation's cancellation deadline, which is often 24 or 48 hours before your scheduled arrival. If you booked a non-refundable reservation, you might be able to cancel it and be given a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Chicago.

What's the best accommodation for a budget-friendly stay in Chicago?

Based on reviews, Congress Plaza Hotel is a popular hotel for our travellers who want a more economical choice, and features free Wi-Fi and 2 restaurants. Other good options for your budget-friendly stay include Hilton Chicago/Magnificent Mile Suites and River Hotel. View all budget hotels in Chicago.

What's the best family accommodation in Chicago?

DoubleTree by Hilton Chicago - Magnificent Mile is a hotel with an outdoor pool and a restaurant, and it's a top choice on Expedia for families. Other good choices for your child-friendly holiday include Hilton Chicago/Magnificent Mile Suites and Courtyard by Marriott Chicago Magnificent Mile. Also, attractions such as Field Museum of Natural History and Chicago Children's Museum are fun for children of all ages. Find more child-friendly accommodations in Chicago.

What is the favourite LGBTQ-friendly place to stay in Chicago?

Freehand Chicago is a top LGBTQ-friendly hotel that features free Wi-Fi and a 24-hour fitness centre. Hilton Chicago/Magnificent Mile Suites and InterContinental Chicago Magnificent Mile by IHG are two other good options for your stay. See all available hotels listed as LGBTQ-friendly in Chicago.

What's the best dog-friendly place to stay in Chicago?

DoubleTree by Hilton Chicago - Magnificent Mile is a top dog-friendly hotel, and offers a restaurant along with MP3 docks for its human guests. Other good options for you and your pet's trip include Hilton Chicago and Hilton Chicago/Magnificent Mile Suites. See more pet-friendly hotel accommodations in Chicago.

What's the best accommodation option for a beach holiday in Chicago?

Inn of Chicago is a top beach hotel offering flat-screen TVs and a cafe, located within a short 10-minute walk of Ohio Street Beach . See more stays near the beach in Chicago.

What's the best luxury place to stay in Chicago?

LondonHouse Chicago, Curio Collection by Hilton is a luxury hotel with 2 restaurants and 2 bars, and it's a popular choice for Expedia travellers looking for an elegant place to stay. InterContinental Chicago Magnificent Mile by IHG and Swissotel - Chicago are other upscale choices for your trip. Find more luxury hotels in Chicago.

What's the best boutique accommodation in Chicago?

Hotel Felix River North/Magnificent Mile is a favourite hotel with Expedia travellers looking for a stylish stay, and features a 24-hour health club and a fireplace in the lobby. Eurostars Magnificent Mile and L7 Chicago by LOTTE are a couple of other boutique hotels. See all boutique hotels in Chicago.

What's the best place to stay if I'm looking to play golf in Chicago?

Country Inn & Suites by Radisson, Chicago O'Hare South, IL is a top hotel that has an adjacent golf course and features free WiFi. Other good options if you'd like to stay near a golf course include Eaglewood Resort and Spa and Hyatt Lodge Oak Brook Chicago. You can tee off at Harborside International Golf Center, The Glen Club or Cog Hill Golf & Country Club while you're in town. See more golf hotels in Chicago.

What are some hotels with pools in Chicago?

Embassy Suites by Hilton Chicago Downtown River North is a top hotel with an indoor pool, free full breakfast and flat-screen TVs. Other choices that offer an on-site pool include Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG and Hilton Garden Inn Chicago Downtown South Loop. View all hotels with pools in Chicago.

What is the best spa hotel in Chicago?

LondonHouse Chicago, Curio Collection by Hilton is a top luxury spa hotel with a fitness centre. Treat yourself to a facial, body scrub or Swedish massage at LH Spa. In-room massages are also available. Other popular spa hotels in Chicago include Eurostars Magnificent Mile and The Langham, Chicago. See all spa hotels in Chicago.

What's the top hotel in Chicago with a water park on site or close by?

Great Wolf Lodge Illinois is a popular resort, featuring free water park access, 6 indoor pools and 5 restaurants. It's located only steps from Great Wolf Lodge Water Park. Take a look at all hotels with or near waterparks in Chicago.

What's it like to stay in Chicago?

Travellers to Chicago give high marks for the popular theatre scene, interesting architecture and fascinating museums. Urban and scenic, this city will delight tourists with its art, monuments and entertainment. Top sights in the city include Michigan Avenue, Wrigley Field and Naval Base Great Lakes. In Chicago, there are 5670 hotels and other accommodation options to choose from. Find out more about Chicago.

What are the top places to visit in Chicago?

Known for its theatres and museums, cultural venues include CIBC Theatre, Symphony Center and Chicago Symphony Orchestra. Attractions such as Field Museum of Natural History, Chicago Children's Museum and Dave & Buster's are fun for children of all ages. Notable for its monuments, landmarks like Chagall's Four Seasons, Daley Plaza and Rookery are not to be missed. Take a look at what more there is to see and do in Expedia's Chicago guide.

What's the best way to get around Chicago?

Walk to nearby metro stations such as Monroe Station (Red Line), Monroe Station (Blue Line) and Adams-Wabash Station. If you want to venture out around the area, you may want a rental car in Chicago for your journey.

What's the seasonal weather in Chicago?

The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are January and February, with an average of -1°C. Average annual precipitation for Chicago is 1260 mm.

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Our top choices for Chicago hotels

River Hotel

Aloft Chicago Mag Mile

Hilton Chicago/Magnificent Mile Suites

Hyatt Centric The Loop Chicago

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Hyatt Regency Chicago

Eurostars Magnificent Mile

The Chicago Hotel Collection Ambassador Gold Coast

Arlo Chicago

citizenM Chicago Downtown

LondonHouse Chicago, Curio Collection by Hilton

Staypineapple, An Iconic Hotel, The Loop

Palmer House a Hilton Hotel

DoubleTree by Hilton Chicago - Magnificent Mile

The Royal Sonesta Chicago Downtown

Club Quarters Hotel Wacker at Michigan, Chicago

Hotel Riu Plaza Chicago

La Quinta Inn & Suites by Wyndham Chicago Downtown

L7 Chicago by LOTTE

Thompson Chicago, by Hyatt

Where to stay in Chicago

The Loop

River North

Magnificent Mile

West Loop

Lincoln Park

Stay near popular Chicago attractions

Wrigley Field

Michigan Avenue

Chicago and related destinations

Top Chicago Hotel Reviews

Hilton Chicago/Magnificent Mile Suites

More cheap stays in Chicago

Motel 6 Naperville, IL

Frequently asked questions

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