Chicago Holiday Rentals, Illinois: Private House Rentals

Our top choices for Chicago hotels

InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

Logan

฿9,481 total

includes taxes & fees

10 May - 11 May

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Mark

฿8,855 total

includes taxes & fees

25 May - 26 May

Hyatt Regency Chicago

Downtown Chicago

Jennifer

฿9,502 total

includes taxes & fees

25 May - 26 May

Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

Judith Daniella

฿6,006 total

includes taxes & fees

10 May - 11 May

Hotel Riu Plaza Chicago

Downtown Chicago

Adam

฿6,598 total

includes taxes & fees

30 Apr - 1 May

Holiday Inn Chicago O'Hare – Rosemont by IHG

Rosemont

Mariam

฿4,464 total

includes taxes & fees

25 May - 26 May

Aloft Chicago Mag Mile

Downtown Chicago

Fedna

฿4,768 total

includes taxes & fees

27 Apr - 28 Apr

Hyatt Place Chicago/Downtown - The Loop

Downtown Chicago

Durron

฿7,208 total

includes taxes & fees

26 Apr - 27 Apr

Swissotel - Chicago

Downtown Chicago

Lorena

฿9,093 total

includes taxes & fees

8 May - 9 May

Hyatt House Chicago West Loop

Downtown Chicago

Thomas

฿6,484 total

includes taxes & fees

10 May - 11 May

Sofitel Chicago Magnificent Mile

Downtown Chicago

Karen

฿9,262 total

includes taxes & fees

25 May - 26 May

Hilton Garden Inn Chicago Central Loop

Downtown Chicago

Stephanie

฿6,306 total

includes taxes & fees

9 May - 10 May

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Downtown Chicago

Angela

฿4,428 total

includes taxes & fees

28 Apr - 29 Apr

Hilton Chicago

Downtown Chicago

Diana

฿7,096 total

includes taxes & fees

25 May - 26 May

Fairmont Chicago at Millennium Park

Downtown Chicago

Nicole

฿7,796 total

includes taxes & fees

8 May - 9 May

DoubleTree by Hilton Chicago - Magnificent Mile

Downtown Chicago

Md

฿5,644 total

includes taxes & fees

26 Apr - 27 Apr

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

L7 Chicago by LOTTE

Downtown Chicago

Joel

฿5,477 total

includes taxes & fees

26 Apr - 27 Apr

Lunch, dinner, brunch served; Mediterranean cuisine

Hyatt Place Chicago/River North

Downtown Chicago

Rose

฿5,253 total

includes taxes & fees

10 May - 11 May

La Quinta Inn & Suites by Wyndham Chicago Downtown

Downtown Chicago

Agnes

฿5,492 total

includes taxes & fees

26 Apr - 27 Apr

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Downtown Chicago

Darin

฿7,038 total

includes taxes & fees

10 May - 11 May

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Holiday Rentals in Chicago

Aparthotel

Sentral Michigan Avenue

Downtown Chicago

"Thank you for the stay"

Aparthotel

50-inch Smart TV with satellite channels

The Neighborhood Hotel-Little Italy

Near West Side

"Great place and location loved the quiet and simple check in"

Aparthotel

River West, Third Floor Chicago by 747 Lofts

West Town

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

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

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."

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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

4.5/5 (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."

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Navy Pier

4.5/5 (24,140 reviews)

This historic Chicago waterfront landmark offers panoramic lake views from its iconic Centennial Wheel. Enjoy seasonal fireworks or interactive exhibits at the Children's Museum while exploring Navy Pier.

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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

Club Quarters Hotel, Central Loop, Chicago

8/10 Good

"Nice to have an espresso machine in the room. Nespresso but decent."

Warwick Allerton - Chicago

6/10 Okay

"The cleanliness was really good I will say, the location was also not so bad either. The stuff was alright but for the issues we had and how cheap it was, it truly couldve been a little better and less "judgy" considering how cheap it was. But we were not very impressed. The rooms were not how they seemed in the photos. It was very misleading. They also didn't mention that the rooms you might get are also connected to the rooms next door and while yes they did have a door over it which you could open and unlock/lock, it was only covered with a very thin wood panel and me and the people beside us could hear everything. Whether it was their full on conversations, or other stuff or them using the bathroom.. did i mention using the bathrooms? I could hear them quite literally GOING to the bathroom the walls are so thin and the separation board was NOT thick enough at all. Also I am not sure if it was our neighbors or what but every random moments we would smell straight sewage and it quite literally woke me up out of bed it was so strong. We had debated on going to another hotel and maybe we should've but it was paid for already and we were only there for a short time. Unfortunately I do not recommend. Maybe if they updated the rooms and made SEPARATE rooms without a thin wood sheet to separate the rooms and fixed the plumbing issue and showed photos of how the rooms truly looked. I would rate it higher but until then, spend the extra money somewhere else. "

More cheap stays in Chicago

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

22 West Algonquin Road Arlington Heights IL

฿1,725

฿1,931 total

8 May - 9 May

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 8-minute walk from Millennium Park, and it offers 2 restaurants and 2 bars. Other good options for your stay include Hotel Felix River North/Magnificent Mile and River Hotel. 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, River Hotel is a popular hotel for our travellers who want a more economical choice, and features free Wi-Fi and air conditioning. Other good options for your budget-friendly stay include Hilton Chicago/Magnificent Mile Suites and Hotel Felix River North/Magnificent Mile. 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 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?

River Hotel is a top dog-friendly hotel, and offers a restaurant and a fitness centre for its human guests. Other good options for you and your pet's trip include Hilton Chicago/Magnificent Mile Suites and Hotel Felix River North/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 free newspapers, 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. Palmer House a Hilton Hotel 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?

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. Central Loop Hotel 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?

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, 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 Holiday Inn & Suites Chicago - Downtown 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?

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 Navy Pier, Wrigley Field and Naval Base Great Lakes. In Chicago, there are 5603 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, Miró's Chicago and Marshall Field Building 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

InterContinental Chicago Magnificent Mile by IHG

Sable at Navy Pier Chicago, Curio Collection by Hilton

Hyatt Regency Chicago

Hilton Chicago/Magnificent Mile Suites

Hotel Riu Plaza Chicago

Holiday Inn Chicago O'Hare – Rosemont by IHG

Aloft Chicago Mag Mile

Hyatt Place Chicago/Downtown - The Loop

Swissotel - Chicago

Hyatt House Chicago West Loop

Sofitel Chicago Magnificent Mile

Hilton Garden Inn Chicago Central Loop

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Hilton Chicago

Fairmont Chicago at Millennium Park

DoubleTree by Hilton Chicago - Magnificent Mile

L7 Chicago by LOTTE

Hyatt Place Chicago/River North

La Quinta Inn & Suites by Wyndham Chicago Downtown

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Holiday Rentals in Chicago

Sentral Michigan Avenue

Where to stay in Chicago

The Loop

River North

Magnificent Mile

West Loop

Lincoln Park

Stay near popular Chicago attractions

Wrigley Field

Navy Pier

Chicago and related destinations

Top Chicago Hotel Reviews

Club Quarters Hotel, Central Loop, Chicago

More cheap stays in Chicago

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

Frequently asked questions

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