Chicago Holiday Rentals, Illinois: Private House Rentals

Our top choices for Chicago hotels

Aloft Chicago Mag Mile

Downtown Chicago

Roxana

฿4,094 total

includes taxes & fees

22 Mar - 23 Mar

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Brian

฿6,553 total

includes taxes & fees

24 Mar - 25 Mar

River Hotel

Downtown Chicago

Ciandra

฿3,834 total

includes taxes & fees

23 Mar - 24 Mar

LIVN - Millennium Park Downtown Chicago

Downtown Chicago

"I had a really great stay at LIVN Millennium Park. The location honestly couldn’t be better and made getting around the city super easy. The apartment was very clean, modern, and comfortable. Everything felt well kept and thoughtfully set up, and it had everything I needed for a relaxing stay. The staff was super friendly and accommodating and the communication throughout the stay was clear and helpful. Overall it was a really convenient and enjoyable place to stay in downtown Chicago. I’d...

Jeremy

฿4,435 total

includes taxes & fees

6 Apr - 7 Apr

Le Méridien Essex Chicago

Downtown Chicago

Kassia

฿3,522 total

includes taxes & fees

5 Apr - 6 Apr

Superior Apartment, 2 Bedrooms, Kitchen | Living area | LED TV, Netflix, Hulu, streaming services

LIVN - West Loop Chicago

Downtown Chicago

John

฿5,042 total

includes taxes & fees

13 Apr - 14 Apr

Premium bedding, in-room safe, desk, blackout curtains

Courtyard by Marriott Chicago Magnificent Mile

Downtown Chicago

Shannon

฿4,503 total

includes taxes & fees

19 Mar - 20 Mar

Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

Michael

฿3,937 total

includes taxes & fees

22 Mar - 23 Mar

The Wade

Downtown Chicago

Tabitha

฿4,890 total

includes taxes & fees

18 Mar - 19 Mar

DoubleTree by Hilton Chicago - Magnificent Mile

Downtown Chicago

Ellen

฿4,010 total

includes taxes & fees

22 Mar - 23 Mar

FOUND Hotel Chicago River North

Downtown Chicago

Abel

฿3,209 total

includes taxes & fees

23 Mar - 24 Mar

Swissotel - Chicago

Downtown Chicago

Natalie

฿5,747 total

includes taxes & fees

29 Mar - 30 Mar

Ivy Boutique Hotel

Downtown Chicago

Tony

Hotel Riu Plaza Chicago

Downtown Chicago

Bianca

฿5,912 total

includes taxes & fees

22 Mar - 23 Mar

citizenM Chicago Downtown

Downtown Chicago

Andrew

฿4,397 total

includes taxes & fees

22 Mar - 23 Mar

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Downtown Chicago

Ricoya

฿3,876 total

includes taxes & fees

24 Mar - 25 Mar

Hyatt Centric Chicago Magnificent Mile

Downtown Chicago

Josh

฿5,800 total

includes taxes & fees

22 Mar - 23 Mar

Lunch, dinner, brunch served; Mediterranean cuisine

Hyatt Place Chicago/River North

Downtown Chicago

Anam

฿4,511 total

includes taxes & fees

7 Apr - 8 Apr

Hilton Chicago

Downtown Chicago

Nia

฿5,890 total

includes taxes & fees

5 Apr - 6 Apr

Rooftop bar, al fresco dining, open daily

The Godfrey Hotel Chicago

Downtown Chicago

Kijuan

฿4,511 total

includes taxes & fees

5 Apr - 6 Apr

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Holiday Rentals in Chicago

Aparthotel

Kasa Magnificent Mile Chicago

Downtown Chicago

"Fantastic location with great amenities and secure."

Aparthotel

50-inch Smart TV with satellite channels

The Neighborhood Hotel-Little Italy

Near West Side

"Nice neighborhood, great hotel!"

Aparthotel

Stylish Apartment near Chicago Downtown

Bridgeport

"When we arrived at the room, the access code didn’t work, so I contacted the host. Unfortunately, I didn’t get a response, so I had to reach out to support. It took two hours to get a response, and they informed me that the access code had been changed. This was quite frustrating. Once I got in, the room was amazing. It felt like I was at home. The only other complaints I have are the noisy furnace and the loud upstairs neighbors. The unit has quiet hours, but we were disturbed by the noise. I...

Aparthotel

Ground Floor Studios in Chicago by 747 Lofts

West Town

"Its was in a good location for anyone who has family close by. Bed was wonderful. "

Aparthotel

Kasa South Loop Chicago

Downtown Chicago

"Shops nearby, clean apartment, good heat/AC, extremely soft beds and great views! A great place to stay! "

Aparthotel

Kasa River North Chicago

Downtown Chicago

"Nice area if you are renting a car, be aware that you would have to pay for street parking or go over a few blocks and park in a parking lot."

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."

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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

Hotel Riu Plaza Chicago

10/10 Excellent

"The room was so clean, the staff were very kind and polite, helpful and made the hotel very welcoming!! The area was also safe and had lots of shopping areas and restaurants! 10/10 would recommend for everyone! Made my friend’s birthday wonderful! Thank you RIU!"

Hilton Chicago/Magnificent Mile Suites

6/10 Okay

"We stayed at Hilton because of the amazing reviews, however we did not experience the magic, we stayed one night and had intentions of staying for the weekend, however it was cut short, walls were very thin, we could hear toilets flushing, doors closing from our neighbors. We were right next to young folks that played video games all night, they were really loud, we tried our best to shut them out and just enjoy our night, but our room was really cold, we thankfully had our blankets, we did not extend our stay at Hilton. This Hotel is definitely for younger adults, we wanted a quiet night but instead kept hearing men yelling at a tv. The room was clean, everything was great with the room, only issue is thin walls! I don't recommend this hotel for anyone that wants a quiet night with their significant other. Also I'm going to add that we got a suite exactly for that reason, to have a quiet night. "

More cheap stays in Chicago

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

฿1,839

฿2,059 total

21 Mar - 22 Mar

includes taxes & fees

6.4/10 (1,065 reviews)

Frequently asked questions

Where is the best place to stay in Chicago?

Wrigleyville Inn is a favourite property for Expedia customers. This guest house is a short 6-minute walk from Wrigley Field, and it offers free parking and in-room kitchens. Traveller reviews also recommend Harvey House Bed & Breakfast and Hampton Inn & Suites Chicago Medical District UIC 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 Eurostars Magnificent Mile and Hilton Chicago/Magnificent Mile Suites. View all budget hotels in Chicago.

What's the best family accommodation in Chicago?

Eurostars Magnificent Mile is a hotel with laundry facilities 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 Embassy Suites by Hilton Chicago Downtown River North. 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?

Hilton Chicago is a top hotel for people travelling with their pets, and offers 2 restaurants and an indoor pool for its human guests. Other good options for you and your pet's trip include Hilton Chicago/Magnificent Mile Suites and Aloft Chicago Mag Mile. 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. L7 Chicago by LOTTE and Palmer House a Hilton Hotel are other upscale choices for your trip. Find more luxury hotels in Chicago.

What's the best boutique accommodation in Chicago?

Eurostars Magnificent Mile is a favourite hotel with Expedia travellers looking for a stylish stay, and features a full-service spa and massages. L7 Chicago by LOTTE and Hotel Felix River North/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?

Hyatt Lodge Oak Brook Chicago is a top hotel that has an adjacent golf course and features a full-service spa. Other good options if you'd like to stay near a golf course include Eaglewood Resort and Spa and Country Inn & Suites by Radisson, Chicago O'Hare South, IL. You can tee off at Oak Brook Golf Course, 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 Hilton Garden Inn Chicago Downtown South Loop and The Ritz-Carlton, Chicago. 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 LondonHouse Chicago, Curio Collection by Hilton and Palmer House a Hilton Hotel. 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 5580 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 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, Marshall Field Building and Daley Plaza 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

Aloft Chicago Mag Mile

Sable at Navy Pier Chicago, Curio Collection by Hilton

River Hotel

LIVN - Millennium Park Downtown Chicago

Le Méridien Essex Chicago

LIVN - West Loop Chicago

Courtyard by Marriott Chicago Magnificent Mile

Hilton Chicago/Magnificent Mile Suites

The Wade

DoubleTree by Hilton Chicago - Magnificent Mile

FOUND Hotel Chicago River North

Swissotel - Chicago

Ivy Boutique Hotel

Hotel Riu Plaza Chicago

citizenM Chicago Downtown

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

Hyatt Place Chicago/River North

Hilton Chicago

The Godfrey Hotel Chicago

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

Michigan Avenue

Chicago and related destinations

Top Chicago Hotel Reviews

Hotel Riu Plaza Chicago

More cheap stays in Chicago

Red Roof Inn PLUS+ Chicago - Willowbrook

Frequently asked questions

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