Chicago Holiday Rentals, Illinois: Private House Rentals

Our top choices for Chicago hotels

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Christopher

฿8,349 total

includes taxes & fees

6 Apr - 7 Apr

Hyatt Regency Chicago

Downtown Chicago

Alejandra

฿9,363 total

includes taxes & fees

6 Apr - 7 Apr

Aloft Chicago Mag Mile

Downtown Chicago

Taneshia

฿4,644 total

includes taxes & fees

12 Apr - 13 Apr

InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

Kinjal

฿8,265 total

includes taxes & fees

7 Apr - 8 Apr

Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

Emre

฿5,260 total

includes taxes & fees

12 Apr - 13 Apr

Hotel Riu Plaza Chicago

Downtown Chicago

Marina

฿5,871 total

includes taxes & fees

28 Apr - 29 Apr

Hilton Garden Inn Chicago Central Loop

Downtown Chicago

Tristen

฿6,262 total

includes taxes & fees

19 Apr - 20 Apr

Hyatt Place Chicago/Downtown - The Loop

Downtown Chicago

Ashlee

฿5,323 total

includes taxes & fees

5 Apr - 6 Apr

DoubleTree by Hilton Chicago - Magnificent Mile

Downtown Chicago

Ellen

฿4,567 total

includes taxes & fees

5 Apr - 6 Apr

Sofitel Chicago Magnificent Mile

Downtown Chicago

Cornelius

฿7,816 total

includes taxes & fees

12 Apr - 13 Apr

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

L7 Chicago by LOTTE

Downtown Chicago

Alisha

฿6,465 total

includes taxes & fees

26 Apr - 27 Apr

Fairmont Chicago at Millennium Park

Downtown Chicago

alyvia

฿8,787 total

includes taxes & fees

5 Apr - 6 Apr

La Quinta Inn & Suites by Wyndham Chicago Downtown

Downtown Chicago

America.

฿5,376 total

includes taxes & fees

5 Apr - 6 Apr

Hyatt House Chicago West Loop

Downtown Chicago

Amy

฿6,089 total

includes taxes & fees

5 Apr - 6 Apr

Hyatt Centric The Loop Chicago

Downtown Chicago

eduardo

฿7,792 total

includes taxes & fees

17 Apr - 18 Apr

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Downtown Chicago

Juliette

฿4,932 total

includes taxes & fees

5 Apr - 6 Apr

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Downtown Chicago

Jennifer

฿4,101 total

includes taxes & fees

12 Apr - 13 Apr

Lunch, dinner, brunch served; Mediterranean cuisine

Hyatt Place Chicago/River North

Downtown Chicago

Aftan

฿5,208 total

includes taxes & fees

12 Apr - 13 Apr

Hilton Chicago

Downtown Chicago

Carrie

฿8,596 total

includes taxes & fees

10 Apr - 11 Apr

Swissotel - Chicago

Downtown Chicago

Fenton

฿9,405 total

includes taxes & fees

10 Apr - 11 Apr

View all properties

Holiday Rentals in Chicago

Aparthotel

Kasa Magnificent Mile Chicago

Downtown Chicago

"Great place "

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

50-inch Smart TV with satellite channels

The Neighborhood Hotel-Little Italy

Near West Side

"Nice neighborhood, great hotel!"

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 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

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

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 (11,695 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

McCormick Place

4.4/5 (9,822 reviews)

McCormick Place hosts major events like the Chicago Auto Show in its 2.6 million square feet of exhibition space. Arrive via the convenient Metra Electric Line station directly beneath the complex.

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

Hotel Riu Plaza Chicago

8/10 Good

"Comfortable Room"

The Chicago Hotel Collection Ambassador Gold Coast

4/10 Poor

"This was such a disappointing and underwhelming stay. There is zero soundproofing in the rooms, (constant door closing can be heard even over my white noise), housekeeping knocked at 8:20am to assess whether we were still in the room and my daughter was still sleeping, poor internet (WiFi was temperamental and TV was constantly losing signal), the terrace was closed/doors locked, pillows are thin and useless, beds are low to the ground, the carpet is stained and dingy, and I had to ask the front desk twice to review my profile bc I had been charged twice (was resolved). The food is such a loss here. If you’ve ever had food at a bowling alley, this is exactly what the line of food tastes like: I ordered beef empanadas and the margheritia pizza. The pizza tasted previously frozen and the empanadas give me Dollar General frozen food. Thank goodness I paid for “room only” and not the food/beverage package. The strong wins: location, and the bar scene/bartender. Valet was also exceptional. Only reason I didn’t give it 1 star. Do not recommend. The pictures do it way more justice than it deserves. If you’re seeking luxury, this is not it. And perhaps I was booked in a “cheap”/non-upgraded room, but this is not worth it."

Hilton Chicago

8/10 Good

"The hotel is very nice overall! We loved the games area in the lobby! Maybe it’s just that they’re extremely short staffed for the size of the place, but when disappointments keep happening you start to feel let down. Expect long lines at the front desk for check in or anything else. We couldn't get a response about getting an extra blanket for the room and they only have an automated system to help you with guest service. We also had to wait a couple hours for our luggage to get to the room after we arrived which was inconvenient. Also, heads up - we weren’t made aware at check in that the pool/hot tub area closes at 9:45 pm and that you need a reservation after 2:30 pm so we weren’t able to use either when we were there. That was a bummer for the kids since that’s why we booked this hotel!"

More cheap stays in Chicago

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

฿1,861

฿2,084 total

15 Apr - 16 Apr

includes taxes & fees

6.4/10 (1,084 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 Hampton Inn & Suites Chicago Medical District UIC and The Guesthouse Hotel 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, Hilton Chicago/Magnificent Mile Suites is a popular hotel for our travellers who want a more economical choice, and features free Wi-Fi and an indoor pool. Other good options for your budget-friendly stay include Congress Plaza Hotel and River Hotel. View all budget hotels in Chicago.

What's the best family accommodation in Chicago?

Hilton Chicago/Magnificent Mile Suites is a hotel with an indoor pool and free cots, and it's a top choice on Expedia for families. Other good choices for your child-friendly holiday include DoubleTree by Hilton Chicago - Magnificent Mile and Eurostars Magnificent Mile. 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/Magnificent Mile Suites is a top hotel for people travelling with their pets, and offers an indoor pool and pillowtop beds for its human guests. Other good options for you and your pet's trip include River Hotel and DoubleTree by Hilton Chicago - Magnificent 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?

Swissotel - Chicago is a luxury hotel with 2 bars and spa services, 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. Hotel Felix River North/Magnificent Mile and The Chicago Hotel Collection - 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 Holiday Inn & Suites Chicago - Downtown by IHG. 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 Fairmont Chicago at Millennium Park. 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 5473 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.

Explore a world of travel with Expedia

More ways to book

Book Hotels in Chicago on Expedia.com

Find hotels in Chicago, IL from ฿2,084

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

Sable at Navy Pier Chicago, Curio Collection by Hilton

Hyatt Regency Chicago

Aloft Chicago Mag Mile

InterContinental Chicago Magnificent Mile by IHG

Hilton Chicago/Magnificent Mile Suites

Hotel Riu Plaza Chicago

Hilton Garden Inn Chicago Central Loop

Hyatt Place Chicago/Downtown - The Loop

DoubleTree by Hilton Chicago - Magnificent Mile

Sofitel Chicago Magnificent Mile

L7 Chicago by LOTTE

Fairmont Chicago at Millennium Park

La Quinta Inn & Suites by Wyndham Chicago Downtown

Hyatt House Chicago West Loop

Hyatt Centric The Loop Chicago

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Hyatt Place Chicago/River North

Hilton Chicago

Swissotel - 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

McCormick Place

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

Explore a world of travel with Expedia

Go further with the Expedia app