Chicago Holiday Rentals, Illinois: Private House Rentals

Our top choices for Chicago hotels

1. Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Deborah

฿10,020 total

includes taxes & fees

30 Jun - 1 Jul

2. InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

Sandra

฿8,766 total

includes taxes & fees

1 Jul - 2 Jul

3. Hyatt Regency Chicago

Downtown Chicago

Marianne

฿9,264 total

includes taxes & fees

6 Jul - 7 Jul

4. Hyatt Place Chicago/Downtown - The Loop

Downtown Chicago

Daniel

฿8,149 total

includes taxes & fees

6 Jul - 7 Jul

5. Hotel Riu Plaza Chicago

Downtown Chicago

Corey

฿7,183 total

includes taxes & fees

30 Jun - 1 Jul

6. Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

Avradita

฿6,272 total

includes taxes & fees

7 Jul - 8 Jul

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

7. L7 Chicago by LOTTE

Downtown Chicago

Peggy

฿11,674 total

includes taxes & fees

3 Jul - 4 Jul

8. Swissotel - Chicago

Downtown Chicago

Sergio

฿8,000 total

includes taxes & fees

5 Jul - 6 Jul

9. Embassy Suites by Hilton Chicago Downtown River North

Downtown Chicago

Krysta

฿8,295 total

includes taxes & fees

1 Jul - 2 Jul

10. Omni Chicago Hotel

Downtown Chicago

Alejandro

฿7,299 total

includes taxes & fees

6 Jul - 7 Jul

2 restaurants; breakfast, lunch and dinner served

11. LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

Robert

฿9,835 total

includes taxes & fees

21 Jun - 22 Jun

12. Sofitel Chicago Magnificent Mile

Downtown Chicago

Ellie

฿10,064 total

includes taxes & fees

6 Jul - 7 Jul

13. Hyatt House Chicago/West Loop-Fulton Market

Downtown Chicago

Heather

฿8,050 total

includes taxes & fees

5 Jul - 6 Jul

14. Hyatt Place Chicago/River North

Downtown Chicago

thao

฿6,628 total

includes taxes & fees

5 Jul - 6 Jul

15. La Quinta Inn & Suites by Wyndham Chicago Downtown

Downtown Chicago

Jane

฿6,579 total

includes taxes & fees

5 Jul - 6 Jul

16. Aloft by Marriott Chicago Mag Mile

Downtown Chicago

Jimmie

฿6,522 total

includes taxes & fees

7 Jul - 8 Jul

17. Hilton Chicago

Downtown Chicago

Ruben

฿10,299 total

includes taxes & fees

30 Jun - 1 Jul

18. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Downtown Chicago

Randy

฿6,905 total

includes taxes & fees

2 Jul - 3 Jul

19. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Downtown Chicago

Joseph

฿9,506 total

includes taxes & fees

6 Jul - 7 Jul

20. The Royal Sonesta Chicago Downtown

Downtown Chicago

Sunil

฿8,823 total

includes taxes & fees

2 Jul - 3 Jul

View all properties

Holiday Rentals in Chicago

Aparthotel

Kasa Magnificent Mile Chicago

Downtown Chicago

"Great place to stay."

Aparthotel

Full-sized fridge, microwave, oven, stovetop

Level Chicago – Old Town

Downtown Chicago

"Very clean and loved the location and amenities with the store on the first floor was fantastic"

Aparthotel

50-inch Smart TV with satellite channels

The Neighborhood Hotel-Little Italy

Near West Side

"Amazing place and would recommend it again"

Aparthotel

Ground Floor Studios in Chicago by 747 Lofts

West Town

"Great area and surprisingly nice room!"

Aparthotel

Kasa South Loop Chicago

Downtown Chicago

"Check in was easy, great location, beautiful views, convenient to what b was planned for the weekend"

Aparthotel

River West, Third Floor Chicago by 747 Lofts

West Town

"Cvs. Dunkin Donuts. Pizza pie all 1-2 blocks walking distance "

Aparthotel

Chicago Third Floor Studio by 747 Lofts

West Town

"Clean, easy to check in, all the household items you’d expect"

Aparthotel

River West, Second Floor Chicago by 747 Lofts

West Town

"I need to somewhere to stay for a night in Chicago and found this place. It had a varying level of reviews but found the property more the suitable for what I paid. Easy to follow instructions to get in, clean, and convienent. They even provide ear plugs to drown out the sounds of the city."

Aparthotel

Chicago Second Floor Studio by 747 Lofts

West Town

"Great location, convenient to downtown and blue line to airport. Everything necessary in unit, comfortable temperature and full kitchen with unique grocery store nearby."

See all holiday rentals

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

Stay near popular Chicago attractions

Wrigley Field

4.5/5 (11,704 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."

See properties

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.

See all hotels in Chicago

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

Top Chicago Hotel Reviews

Travelodge by Wyndham Downtown Chicago

8/10 Good

"Everything was okay"

Hotel Felix River North/Magnificent Mile

8/10 Good

"Hotel Felix was in a fantastic location. The staff were very friendly. Our room on the 9th floor with 2 double beds was small, with only a mini fridge. The curtains were old and difficult to open and close. The WiFi would drop or was very slow. The television also provided issues, turning off or to the starting screen, multiple times. The hotel offered only coffee/tea and fresh fruit until 9am. The staff made our stay more enjoyable."

More cheap stays in Chicago

Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts

22 West Algonquin Road Arlington Heights IL

฿2,036

฿2,280 total

22 Jun - 23 Jun

includes taxes & fees

5.4/10 (1,004 reviews)

Frequently asked questions

Where is the best place to stay in Chicago?

Based on our traveller data, Congress Plaza Hotel is one of the top choices for your stay. This hotel is a short 4-minute walk from State Street, and it offers 2 restaurants and 2 bars. Other good options for your stay include The Chicago Hotel Collection - Magnificent Mile and Hotel Riu Plaza Chicago. 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 River Hotel and Hilton Chicago/Magnificent Mile Suites. View all budget hotels in Chicago.

What's the best family accommodation in Chicago?

The Chicago Hotel Collection - Magnificent Mile is a hotel with 2 restaurants and free WiFi, 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 Crowne Plaza Chicago West Loop by IHG. Also, attractions such as Six Flags Great America and Field Museum of Natural History 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?

The Chicago Hotel Collection - Magnificent Mile is a top dog-friendly hotel, and offers 2 restaurants along with free WiFi for its human guests. Other good options for you and your pet's trip include River Hotel and Freehand Chicago. 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 bar, 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?

Palmer House a Hilton Hotel is a luxury hotel with a full-service spa and a 24-hour health club, and it's a popular choice for Expedia travellers looking for an elegant place to stay. InterContinental Chicago Magnificent Mile by IHG and LondonHouse Chicago, Curio Collection by Hilton are other upscale choices for your trip. Find more luxury hotels in Chicago.

What's the best boutique accommodation in Chicago?

The Chicago Hotel Collection - Magnificent Mile is a favourite hotel with Expedia travellers looking for a stylish stay, and features 2 restaurants and 2 bars. Hotel Felix River North/Magnificent Mile and Eurostars Magnificent Mile 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?

Eaglewood Resort and Spa is a top resort that has a golf course and features a full-service spa. Other good options if you'd like to stay near a golf course include Hyatt Lodge Oak Brook Chicago and Country Inn & Suites by Radisson, Chicago O'Hare South, IL. You can tee off at Oak Brook Golf Course, Glenview Park Golf Club or The Glen 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 Embassy Suites by Hilton Chicago O'Hare Rosemont and Hilton Garden Inn Chicago Downtown South Loop. View all hotels with pools in Chicago.

What is the best spa hotel in Chicago?

Eurostars Magnificent Mile is a top boutique spa hotel with a fitness centre. Enjoy a facial, body scrub or Swedish massage at the on-site spa. Other popular spa hotels in Chicago include Palmer House a Hilton Hotel and LondonHouse Chicago, Curio Collection by Hilton. 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, Soldier Field and Navy Pier. In Chicago, there are 5531 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 Art Institute of Chicago, CIBC Theatre and Symphony Center. Attractions such as Six Flags Great America, Field Museum of Natural History and Chicago Children's Museum 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.

Explore a world of travel with Expedia

More ways to book

Book Hotels in Chicago on Expedia.com

Find hotels in Chicago, IL from ฿2,280

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Chicago (and vicinity)

Check prices for these dates

Filter by

Our top choices for Chicago hotels

1. Sable at Navy Pier Chicago, Curio Collection by Hilton

2. InterContinental Chicago Magnificent Mile by IHG

3. Hyatt Regency Chicago

4. Hyatt Place Chicago/Downtown - The Loop

5. Hotel Riu Plaza Chicago

6. Hilton Chicago/Magnificent Mile Suites

7. L7 Chicago by LOTTE

8. Swissotel - Chicago

9. Embassy Suites by Hilton Chicago Downtown River North

10. Omni Chicago Hotel

11. LondonHouse Chicago, Curio Collection by Hilton

12. Sofitel Chicago Magnificent Mile

13. Hyatt House Chicago/West Loop-Fulton Market

14. Hyatt Place Chicago/River North

15. La Quinta Inn & Suites by Wyndham Chicago Downtown

16. Aloft by Marriott Chicago Mag Mile

17. Hilton Chicago

18. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

19. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

20. The Royal Sonesta Chicago Downtown

Holiday Rentals in Chicago

Kasa Magnificent Mile Chicago

Where to stay in Chicago

The Loop

River North

Magnificent Mile

West Loop

Lincoln Park

Stay near popular Chicago attractions

Wrigley Field

Chicago and related destinations

Top Chicago Hotel Reviews

Travelodge by Wyndham Downtown Chicago

More cheap stays in Chicago

Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app