Chicago Holiday Rentals, Illinois: Private House Rentals

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Our top choices for Chicago hotels

Downtown Chicago

1. Hyatt Regency Chicago

Downtown Chicago

Emily

9.072.992 ₫ total

includes taxes & fees

16 Aug - 17 Aug

2. Hotel Riu Plaza Chicago

Downtown Chicago

Deanne

7.471.724 ₫ total

includes taxes & fees

23 Aug - 24 Aug

3. InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

Jose

8.804.759 ₫ total

includes taxes & fees

17 Aug - 18 Aug

2 restaurants; breakfast, lunch and dinner served

4. LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

Yolanda

7.872.681 ₫ total

includes taxes & fees

9 Aug - 10 Aug

5. Hyatt Place Chicago/Downtown - The Loop

Downtown Chicago

Kimberly

7.101.899 ₫ total

includes taxes & fees

23 Aug - 24 Aug

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

6. L7 Chicago by LOTTE

Downtown Chicago

Julie Ann

6.222.765 ₫ total

includes taxes & fees

17 Aug - 18 Aug

7. Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

Jennifer

5.785.387 ₫ total

includes taxes & fees

16 Aug - 17 Aug

8. Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Downtown Chicago

Aleace

6.234.283 ₫ total

includes taxes & fees

19 Aug - 20 Aug

9. citizenM Chicago Downtown

Downtown Chicago

lakadria

6.444.897 ₫ total

includes taxes & fees

9 Aug - 10 Aug

10. Eurostars Magnificent Mile

Downtown Chicago

Jacey LeeAnn

6.257.181 ₫ total

includes taxes & fees

9 Aug - 10 Aug

11. La Quinta Inn & Suites by Wyndham Chicago Downtown

Downtown Chicago

Diana

6.128.816 ₫ total

includes taxes & fees

9 Aug - 10 Aug

12. The Royal Sonesta Chicago Downtown

Downtown Chicago

Alexis

7.067.975 ₫ total

includes taxes & fees

23 Aug - 24 Aug

13. Arlo Chicago

Downtown Chicago

Shaylah

7.272.225 ₫ total

includes taxes & fees

16 Aug - 17 Aug

Outdoor pool, pool cabanas (surcharge), pool umbrellas

14. DoubleTree by Hilton Chicago - Magnificent Mile

Downtown Chicago

Macy

6.303.484 ₫ total

includes taxes & fees

16 Aug - 17 Aug

15. Hyatt Place Chicago/River North

Downtown Chicago

Michelle

5.318.604 ₫ total

includes taxes & fees

9 Aug - 10 Aug

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

16. Courtyard by Marriott Chicago Magnificent Mile

Downtown Chicago

Zachary

6.726.469 ₫ total

includes taxes & fees

20 Aug - 21 Aug

17. Aloft by Marriott Chicago Mag Mile

Downtown Chicago

Donna

5.850.463 ₫ total

includes taxes & fees

9 Aug - 10 Aug

Presidential Suite, 1 Bedroom, Non Smoking | Premium bedding, in-room safe, desk, blackout curtains

18. Hotel 55 Chicago Downtown

Downtown Chicago

Mohammad

6.134.332 ₫ total

includes taxes & fees

9 Aug - 10 Aug

19. River Hotel

Downtown Chicago

yenedit

6.461.122 ₫ total

includes taxes & fees

24 Aug - 25 Aug

Breakfast, lunch, dinner and brunch served

20. The Royal Sonesta Chicago River North

Downtown Chicago

Andrea

7.070.759 ₫ total

includes taxes & fees

24 Aug - 25 Aug

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Holiday Rentals in Chicago

Aparthotel

Kasa Magnificent Mile Chicago

Downtown Chicago

"Nice ez stay convenient location"

Aparthotel

Full-sized fridge, microwave, oven, stovetop

Level Chicago – Old Town

Downtown Chicago

"We only stayed one night but we definitely want to go back and stay at least two nights. It really was beautiful, clean and very secure."

Aparthotel

50-inch Smart TV with satellite channels

The Neighborhood Hotel-Little Italy

Near West Side

"Loved the style of this hotel. Great location, clean, and good restaurants in walking distance."

Aparthotel

Kasa South Loop Chicago

Downtown Chicago

"Had to extend my stay, I was able to get excellent help and the transaction was smooth. Recommended, I already booked my next stay."

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Where to stay in Chicago

Find the best Chicago areas for the activities you enjoy most.

A river with yellow boats, a bridge, and tall buildings.

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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A city street with a train passing overhead, cars, pedestrians, and a red brick building.

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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A historic castle-like building with intricate stonework and a paved walkway.

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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A cityscape with modern skyscrapers and a curved highway.

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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A river with a city skyline in the background, surrounded by green trees and grass.

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

An aerial view of a baseball stadium surrounded by urban buildings.

Wrigley Field

9.0/10 (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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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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A river with a yellow boat, surrounded by tall buildings and a bridge.

Top Chicago Hotel Reviews

The Allegro Royal Sonesta Hotel Chicago Loop

10/10 Excellent

"Great"

River Hotel

8/10 Good

"The location was perfect—right next to the Hello Kitty Cafe and the Chicago River, which I absolutely loved! The room was clean and comfortable for my 24-hour stay. I probably should have booked the standard room, but this one still worked out well. The staff was very friendly and helpful throughout my stay. Overall, I had a great experience and would definitely stay here again. Thank you so much!"

Warwick Allerton - Chicago

8/10 Good

"We had a great stay for one night. The location is excellent, right on the main shopping street and within easy walking distance of lots of shops and attractions. The hotel offers reasonably priced luggage storage, which was really convenient, and we were able to check in early for an additional fee, which was worth it after travelling. There’s also a good café in the hotel, perfect for grabbing breakfast or a coffee. The room was a little small and slightly dated, but it was clean, comfortable, and perfectly adequate for what we needed for a one-night stay. Overall, we’d definitely stay here again for the location and convenience."

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent

"Nice pool and fitness center. The room was basic two double beds but outlets only available between the beds. This does not work well when two people want to charge their phones. Luggage can be checked for the day after checkout at the bell desk, but the process was inefficient and slow. Only 4 elevators for 26 floors. Parking across the street at Nordstrom's (enter on Rush) was convenient, booked through Spothero, and saved $40 over valet parking. All in all, you are paying for the location."

More cheap stays in Chicago

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

1.543.151 ₫

1.728.021 ₫ total

11 Aug - 12 Aug

includes taxes & fees

Hotels in Chicago with star rating

Frequently asked questions

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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Find hotels in Chicago, IL from 1.728.021 ₫

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Our top choices for Chicago hotels

1. Hyatt Regency Chicago

2. Hotel Riu Plaza Chicago

3. InterContinental Chicago Magnificent Mile by IHG

4. LondonHouse Chicago, Curio Collection by Hilton

5. Hyatt Place Chicago/Downtown - The Loop

6. L7 Chicago by LOTTE

7. Hilton Chicago/Magnificent Mile Suites

8. Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

9. citizenM Chicago Downtown

10. Eurostars Magnificent Mile

11. La Quinta Inn & Suites by Wyndham Chicago Downtown

12. The Royal Sonesta Chicago Downtown

13. Arlo Chicago

14. DoubleTree by Hilton Chicago - Magnificent Mile

15. Hyatt Place Chicago/River North

16. Courtyard by Marriott Chicago Magnificent Mile

17. Aloft by Marriott Chicago Mag Mile

18. Hotel 55 Chicago Downtown

19. River Hotel

20. The Royal Sonesta Chicago River North

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

The Allegro Royal Sonesta Hotel Chicago Loop

More cheap stays in Chicago

Red Roof Inn PLUS+ Chicago - Willowbrook

Hotels in Chicago with star rating

Frequently asked questions

Explore a world of travel with Expedia

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