Holiday rentals in Chicago, IL

Search among 1317 available holiday rentals in Chicago from 50+ providers

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8.4
Great47 reviews
The largest option:
4 adults
Map
1.2 km from City Centre300 m from Chicago Riverwalk
Situated in the Chicago Loop district, 0.9 km from Chicago Riverwalk, the apartment features an indoor pool and entertainment activities.
From£ 161 /nightSelect
8.4
Great3 reviews
8 adults
2 bedrooms
2 beds
Map
7.4 km from City Centre
From£ 106 /nightSelect
5430 Happy HomeHomestay
8.6
Great21 reviews
The largest option:
2 adults
1 bedroom
1 bed
Map
9.0 km from City Centre
From£ 33 /nightSelect
7.0
Very good3 reviews
The largest option:
5 adults
2 bedrooms
3 beds
Map
8.0 km from City Centre300 m from Wrigley Field
Nestled in the Lakeview district of the city, the venue is about 25 km from Midway International airport.
From£ 108 /nightSelect
8 adults
3 bedrooms
5 beds
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7.9 km from City Centre500 m from Viaduct Center
From£ 215 /nightSelect
9.0
Perfect1 review
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7.6 km from City Centre
A fully equipped kitchen and refrigerators, an oven and a washing machine are provided at this 139 m² apartment, which is located in the Bronzeville district, near Liberty Baptish Church.
From£ 275 /nightSelect
8.0
Great1 review
Map
5.9 km from City Centre
This 84 m² property in Chicago is situated a short stroll from Saint Clement Roman Catholic Church and a 10-minute walk from Diversey underground station.
From£ 137 /nightSelect
7.0
Very good1 review
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7.1 km from City Centre1.1 km from Norford Hotel
Placed 7 km from Skydeck Chicago, the property consists of 2 bedrooms, 1 bathrooms and a fully-fitted kitchen.
From£ 116 /nightSelect
7.8
Very good1 review
The largest option:
10 adults
1 bedroom
3 beds
Map
8.0 km from City Centre
Featuring a kitchen with a microwave, a dishwasher and coffee & tea making facilities, this apartment is a perfect place to stay in the Roscoe Village district.
From£ 179 /nightSelect
8.0
Great1 review
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13.4 km from City Centre
This 121 m² accommodation consists of 3 bedrooms, a kitchen and 1 bathrooms.
From£ 127 /nightSelect
7.0
Very good1 review
4 adults
2 bedrooms
3 beds
Map
5.7 km from City Centre
Located in Chicago, and a short stroll from Greater Exodus Baptist Church, this venue includes a fully furnished kitchen with coffee and tea making facilities, refrigerators, and an oven, as well as 1 bathrooms.
From£ 105 /nightSelect
2 adults
1 bedroom
1 bed
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6.8 km from City Centre1.4 km from Wrigley Field
Placed 1.4 km from Wrigley Field, the property consists of 2 bedrooms, 1 bathrooms and a kitchen.
From£ 209 /nightSelect
6 adults
3 bedrooms
3 beds
Map
14.9 km from City Centre1.3 km from Loyola University Chicago
This 88 m² property in Chicago is situated a short stroll from Pottawattomie Park and a 5-minute walk from Morse underground station.
From£ 134 /nightSelect
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9.9 km from City Centre1.4 km from Cannella School of Hair Design
The Home 6 Bd 4 Ba Home With 2 Car Garage Parking is located 15 km from Midway International airport and 350 metres of Armitage & Kolmar EB bus stop.
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2.1 km from City Centre1.3 km from United Center
Cloud Gate is 10 minutes by car from the 2F Chicago'S Little Italy Near West Loop & Downtown, while 360 Chicago Observation Deck is nearly a 10-minute ride away.
From£ 169 /nightSelect
9.0
Perfect1 review
Map
11.1 km from City Centre
This 12 m² property in Chicago is situated a short stroll from Greater Englewood Parish United Methodist church and a 10-minute walk from Halsted underground station.
From£ 46 /nightSelect
9.0
Perfect1 review
2 adults
1 bedroom
1 bed
Map
9.1 km from City Centre1.4 km from Wrigley Field
The apartment comes with air-conditioned bedrooms and is situated 4.6 km from Lincoln Park Conservatory.
From£ 46 /nightSelect
My Cozy HeavonApartment
9.0
Perfect1 review
4 adults
2 bedrooms
3 beds
Map
5.7 km from City Centre
From£ 101 /nightSelect
Webster HouseApartment
9.8
Perfect1 review
3 adults
1 bedroom
2 beds
Map
5.1 km from City Centre300 m from Lincoln Park Hospital
From£ 133 /nightSelect
9.0
Perfect1 review
Map
2.8 km from City Centre600 m from McCormick Place
Offering an equipped kitchen with a fridge, an oven and kitchenware, the venue is located 30 minutes' walking distance from the centre of Chicago.
From£ 284 /nightSelect
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FAQs about holiday lettings in Chicago

Our FAQ covers 10 frequently asked questions about holiday homes in Chicago.

What are the most popular holiday rentals in O'Hare area?

Our guests usually stay in top-rated holiday houses in such districts as — Hyde Park, Lincoln Park and South Loop.

What are the most popular luxury holiday rentals in Chicago?

These luxury accommodations will make your journey memorable: Explore Museum Campus From A Luxury Apartment In South Loop and Reserve Rentals South Loop. Go here to see more holiday rentals.

What are the top pet-friendly holiday rentals in Chicago?

2142 West Walton Apartment is an excellent choice among 16 pet-friendly holiday rentals in Chicago.

What are the best budget holiday rentals to stay in Chicago?

You might choose Near South Side Apartment at the cost of 126£ per night. Click here to see more cheap accommodation options.

How much does a 3-bedroom holiday house cost for a week?

For a 3-bedroom holiday rental in Chicago you might spend about 1491£. Check this popular option — Swank Victorian Near United Center W/ Backdeck.

What are the top-ranked holiday apartments next to a beach?

If you are searching for a beach villa, Family Retreat Chicago is a great option to consider.

What are the top-ranked holiday rentals with swimming pools in Chicago?

According to 0 reviews, Uchicago, Shops, Lake With Gym, W&D By Zencity and Envitae 2Br Vibrant High-Rise Penthouse are the best holiday places in Chicago, which feature a swimming pool on site.

What are the most popular holiday rentals providing free Wi-Fi?

According to guest ranking above 3.5/5, the best property providing free wi-fi is Mccormick Place Guest House.

What are the best holiday rentals near Lincoln Park Zoo?

Sonder North Lincoln is the most popular holiday accommodation not far from Lincoln Park Zoo, one of the top Chicago attractions.

What are the top Chicago holiday rentals featuring free parking?

The best places providing free parking are Chicago Guest House On Henderson Street and Roscoe Village Guesthouse, which offer a patio and complimentary parking.

Holiday rentals in Chicago

Handpicked holiday rentals in Chicago

When on journey, all you need is a nice apartment to relax and enjoy your time off work. There's a selection of apartments and other accommodations near Millennium Park and Navy Pier. Surf available options and reserve the finest accommodation right away!

Exclusive luxury places to stay in Chicago

If luxury is your passion, head to Chicago, where a huge range of luxury vacations houses are waiting for you. If you are looking for a low-key getaways take a look at 8 cheap apartments in Chicago Loop district. With just a few clicks you'll get the most exclusive place to stay in Chicago.

High graded cheap holiday homes in Chicago

How about getting same value for less money? Save time and money booking cheap Chicago accommodation. If you're looking for budget accommodation, check out a list of cheap holiday rentals in Chicago that we thoroughly hand-picked for you from our providers. Go and see yourself!

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Holiday rentals in Chicago essential information

🏨 Holiday rentals in Chicago 1317
👛 Lowest price 31 GBP
✍️ Holiday rentals Reviews 231
Guest reviews of hotels in Chicago