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Holiday homes and lettings in Chicago

Find 5,477 available offers from 11 partners
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Top 15 Recommended holiday lettings in Chicago

Find your perfect holiday home, apartment or cottage in Chicago from just £60 per night!

Bed and breakfast Legends South
24 May - 31 May
Free cancellation
Bed and breakfast ∙ 4 guests ∙ 1 bedroom

Bed & breakfast with garden

Legends South, Chicago, Illinois, United States
£106
per night
Very good
Agoda
£106
per night
View deal
Agoda
Bed and breakfast Bronzeville
17 Jun - 24 Jun
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Nice bed and breakfast with 1 room for 2 persons

Bronzeville, Chicago, Illinois, United States
£79
per night
Agoda
£79
per night
View deal
Agoda
Bed and breakfast Magnolia Glen
-28%
17 Jun - 24 Jun
Bed and breakfast ∙ 4 guests ∙ 1 bedroom

Nice bed and breakfast with garden, pool & terrace

Magnolia Glen, Chicago, Illinois, United States
£269£194
per night
Outstanding
Agoda
£269£194
per night
View deal
Agoda
Bed and breakfast Avondale
11 Jul - 18 Jul
Free cancellation
Bed and breakfast ∙ 4 guests ∙ 1 bedroom

B&B for 4 persons

Avondale, Chicago, Illinois, United States
£128
per night
Agoda
£128
per night
View deal
Agoda
Bed and breakfast Sheffield & DePaul
-28%
4 Aug - 11 Aug
Bed and breakfast ∙ 6 guests ∙ 2 bedrooms

B&B with garden, jacuzzi & terrace

Sheffield & DePaul, Chicago, Illinois, United States
£395£283
per night
Good
Agoda
£395£283
per night
View deal
Agoda
Bed and breakfast Canaryville
4 Jun - 11 Jun
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & breakfast for 2 persons

Canaryville, Chicago, Illinois, United States
£49
per night
Agoda
£49
per night
View deal
Agoda
Bed and breakfast Bridgeport
17 Jun - 24 Jun
Bed and breakfast ∙ 4 guests ∙ 1 bedroom

Bed and breakfast for 4 persons

Bridgeport, Chicago, Illinois, United States
£103
per night
Agoda
£103
per night
View deal
Agoda
Bed and breakfast Kenwood
-31%
17 Jun - 24 Jun
Free cancellation
Bed and breakfast ∙ 3 guests ∙ 1 bedroom

Nice bed & breakfast for 3 persons

Kenwood, Chicago, Illinois, United States
£147£101
per night
Agoda
£147£101
per night
View deal
Agoda
Bed and breakfast Bridgeport
-40%
14 Jun - 21 Jun
Bed and breakfast ∙ 9 guests ∙ 3 bedrooms

Wonderful bed and breakfast with 3 rooms for 9 persons

Bridgeport, Chicago, Illinois, United States
£383£230
per night
Outstanding
Agoda
£383£230
per night
View deal
Agoda
Bed and breakfast Old Town
-40%
6 Jul - 13 Jul
Free cancellation
Bed and breakfast ∙ 3 guests ∙ 1 bedroom

Bed & breakfast with terrace

Old Town, Chicago, Illinois, United States
£324£194
per night
Outstanding
Agoda
£324£194
per night
View deal
Agoda
Bed and breakfast Wicker Park
-20%
7 Jul - 14 Jul
Bed and breakfast ∙ 6 guests ∙ 1 bedroom

Wonderful bed and breakfast for 6 persons

Wicker Park, Chicago, Illinois, United States
£324£259
per night
Outstanding
Agoda
£324£259
per night
View deal
Agoda
Bed and breakfast Woodlawn
-40%
17 Jun - 24 Jun
Free cancellation
Bed and breakfast ∙ 3 guests ∙ 1 bedroom

Lovely bed & breakfast | Perfect for remote work

Woodlawn, Chicago, Illinois, United States
£218£131
per night
Agoda
£218£131
per night
View deal
Agoda
Bed and breakfast River North
28 Jun - 5 Jul
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Beautiful bed & breakfast with 1 room for 2 persons

River North, Chicago, Illinois, United States
£152
per night
Agoda
£152
per night
View deal
Agoda
Bed and breakfast Fulton Market
29 Jun - 6 Jul
Bed and breakfast ∙ 127 guests ∙ 1 bedroom

Bed and breakfast for 127 persons

Fulton Market, Chicago, Illinois, United States
£239
per night
Outstanding
Agoda
£239
per night
View deal
Agoda
Bed and breakfast Boystown
-88%
8 Jun - 15 Jun
Free cancellation
Bed and breakfast ∙ 12 guests ∙ 5 bedrooms

Bed and breakfast with 5 rooms for 12 persons

Boystown, Chicago, Illinois, United States
£1,715£204
per night
Agoda
£1,715£204
per night
View deal
Agoda

Holiday lettings and apartments with air conditioning

House  Cicero
from £178 per night
House ∙ 8 guests ∙ 5 bedrooms

Family-oriented big house with garden | Dogs allowed

Cicero, Cicero Township, Illinois, United States
Air conditioning
Vrbo
View deal
Apartment  Berwyn
from £106 per night
Apartment ∙ 6 guests ∙ 2 bedrooms

Family-friendly beautiful apartment with terrace, BBQ & garden | City view | Perfect for remote work

5.0
Outstanding(17 ratings)
Berwyn, Cook County, Illinois, United States
Air conditioning
Vrbo
View deal
House  Oak Park
from £168 per night
House ∙ 9 guests ∙ 5 bedrooms

Holiday home with garden & terrace | Perfect for remote work

3.1
(4 ratings)
Oak Park, Oak Park Township, Illinois, United States
Air conditioning
Vrbo
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Best holiday homes with a patio or terrace

House  Berwyn
from £180 per night
House ∙ 8 guests ∙ 4 bedrooms

Holiday home with garden & terrace | Good for workation

5.0
Outstanding(25 ratings)
Berwyn, Cook County, Illinois, United States
Balcony/Patio
Vrbo
View deal
House  Berwyn
from £123 per night
House ∙ 6 guests ∙ 3 bedrooms

House with terrace, barbecue & garden | Nature view | Perfect for remote work

5.0
Outstanding(27 ratings)
Berwyn, Cook County, Illinois, United States
Balcony/Patio
Vrbo
View deal
House  Berwyn
from £284 per night
House ∙ 8 guests ∙ 4 bedrooms

Holiday home with garden, terrace & barbecue | City view | Good for workation

4.9
Outstanding(39 ratings)
Berwyn, Cook County, Illinois, United States
Balcony/Patio
Vrbo
View deal
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Most popular holiday lettings with a fireplace

House  Berwyn
from £132 per night
House ∙ 5 guests ∙ 2 bedrooms

House with barbecue

5.0
Outstanding(1 rating)
Berwyn, Cook County, Illinois, United States
Fireplace
Vrbo
View deal
House  Berwyn
from £285 per night
House ∙ 8 guests ∙ 4 bedrooms

House | Good for workation

Berwyn, Cook County, Illinois, United States
Fireplace
Vrbo
View deal
Motel  Archer Heights
from £101 per night
Motel ∙ 2 guests ∙ 1 bedroom

Motel for 2 persons

3.2
(977 ratings)
Archer Heights, Chicago, Illinois, United States
Fireplace
HomeToGo
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Best holiday rental deals in Chicago

Save up to 55%

House Oak Park
6 Jul - 13 Jul
-47%
£327
£174 per night
House ∙ 9 guests ∙ 3 bedrooms

Family-oriented holiday home with garden | Pets are welcome

Oak Park, Oak Park Township, Illinois, United States
Free cancellation
HomeToGo
View deal
Condo Berwyn
24 Jan - 31 Jan
-55%
£458
£208 per night
Condo ∙ 6 guests ∙ 3 bedrooms

Flat with garden

5.0
Outstanding(1 rating)
Berwyn, Cook County, Illinois, United States
Free cancellation
HomeToGo
View deal

5,477 top quality rentals from 11 different partner websites, such as HomeToGo and Booking.com, are currently available in Chicago. By comparing these different offers, HomeToGo features the most economical offers and the highest rated properties in Chicago.

Budget-friendly Holiday Homes in Chicago

Find Fantastic yet Cheap Lettings

House Cicero
4 Jun - 11 Jun
£344 per night
House ∙ 6 guests ∙ 2 bedrooms

House | Dogs allowed

Cicero, Cicero Township, Illinois, United States
Agoda
View deal
Bed and breakfast Wrigleyville
from £195 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Lovely bed and breakfast with garden | Perfect for remote work

Wrigleyville, Chicago, Illinois, United States
Vrbo
View deal
Bed and breakfast Douglas
from £170 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Beautiful bed and breakfast with terrace | Perfect for remote work

3.7
Good(3 ratings)
Douglas, Chicago, Illinois, United States
Vrbo
View deal

Top-Rated Lettings and Properties in Chicago

Book Holiday Letting Offers with the Highest User Rating

Bed and breakfast West Loop
from £273 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & breakfast for 2 persons

4.9
Outstanding(166 ratings)
West Loop, Chicago, Illinois, United States
HomeToGo
View deal
Bed and breakfast West Loop
from £295 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Pleasant bed and breakfast for 2 persons

4.9
Outstanding(166 ratings)
West Loop, Chicago, Illinois, United States
HomeToGo
View deal
Bed and breakfast West Loop
from £218 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

B&B for 2 persons

4.9
Outstanding(166 ratings)
West Loop, Chicago, Illinois, United States
HomeToGo
View deal

Why choose HomeToGo?

Securely pay and stay your way

Securely pay and stay your way

Choose local, trusted payment methods, plus trip insurance and add-on services.

Award-winning customer service

Award-winning customer service

Experience seamless, hands-on support for any booking questions or concerns.

Verified reviews

Verified reviews

Trust in the quality and comfort of your stay with verified guest reviews.

Price clarity, no surprises

Price clarity, no surprises

Spend your budget exactly as planned by comparing thousands of providers.

Smart search made simple

Smart search made simple

Transform holiday planning into a joy with advanced, AI-powered search tools.

Find your dream stay

Find your dream stay

Explore 15 million+ rentals, the world’s biggest selection of holiday homes.

Popular holiday rental amenities in Chicago

  • Pool (1,812)
  • WiFi (5,338)
  • Kitchen (1,004)
  • Air conditioning (5,377)
  • Washing machine (1,612)
  • TV (4,863)
  • Parking (1,356)
  • Balcony/patio (1,591)
  • Pet-friendly (2,231)
  • Microwave (1,799)
  • No smoking (5,339)
  • Dishwasher (460)

You will have a lot of holiday rentals from which to choose if you are looking for a short stay accommodation providing a pool in Chicago. More hotel room have a pool than aparthotel. Most of the hotel room with pools in Chicago can welcome 8 guests and have an average cost of £329 a night. If you would also like to be near the water, two-thirds of the properties offering a pool are within 2 kilometres of the waterfront.

Price and Availability Index for Chicago

Click on any bar to see price and availability information

Holiday Letting Price Information in Chicago

The graph shows average prices of holiday lettings in Chicago for the next twelve months. Holiday rental prices are the highest in May (31/05 – 07/06). The cheapest week in which to book a holiday home is in June (28/06 – 05/07).

Rental availability information in Chicago

The availability graph shows the percentage of available holiday homes in Chicago. The busiest time to book a holiday letting in Chicago so far is in December (06/12 – 13/12), where only 5 rentals are available. People tend to travel to Chicago least during a week in July (12/07 – 19/07) when only 35% of the rentals are booked.

Enjoy a fun and cultural trip with Chicago holiday accommodation

The historic city of Chicago boasts a fabulous skyline and a profusion of world-class museums, art galleries, jazz clubs, and playhouses. A walk through downtown Chicago will reveal some of the world's best architectural styles: Gothic, classic, modernist, and more.

The winds that blow across Lake Michigan have earned Chicago a nickname as the Windy City. Check in at your Chicago holiday apartment and find out what the fuss is all about.

What are the best activities for families in Chicago?

Family holidays in Chicago

Chicago has plenty to keep kids occupied. Right along the lake on Museum Campus lie three institutions in walking distance of each other. The Adler Planetarium has the coolest astronomy shows and exhibits, while the Shedd Aquarium features majestic sharks, dolphins, whales, and other superb marine life. The kids will love the giant Tyrannosaurus Rex skeleton in the Field Museum of Natural History. How about a picnic on the clean shores of Lake Michigan to finish up? The waters are safe and excellent for swimming.

What are the best places to discover the arts and culture of Chicago?

Art and culture in Chicago

Art and history enthusiasts will be spoilt for choice with the variety of art galleries and museums scattered across the city. The Art Institute of Chicago in the Loop district houses priceless Impressionist and Modernist works, and there's also the National Museum of Mexican Art in Pilsen, the Museum of Photography, the Polish Museum of America in Wicker Park, the International Museum of Surgical Science, and so on. Buy the Chicago CityPASS to save money if you plan on visiting several attractions in a short span of time.

For improvisational comedy and performance art, catch a show at The Annoyance Theatre, I.O., or the Playground. Steppenwolf in Lincoln Park is more serious, having hosted the likes of John Malkovich. Visit the Auditorium in the Loop for its architecture and brilliant use of performance space. For rock, blues, jazz, and spoken-word performances, the Chicago Theatre awaits.

What are the top sights in Chicago?

What to do and see in Chicago

The city's most popular attraction is the Lincoln Park Zoo, which houses African Apes and other interesting species. Trivia lovers will be impressed to learn that Chicago is home to three out of America's five tallest buildings: the Sears Tower, Trump Tower, and the Aon Centre.

Chicago's ethnic neighborhoods are so true-to-life, you'd be forgiven for thinking you were genuinely in another country. There's Chinatown, the Korean community in Lawrence Avenue, the Swedish settlement at Andersonville, Little Italy, Greektown, and several other international pockets. The Polish Cathedrals of St. Mary of the Angels in Bucktown and St. Hyacinth Basilica in Avondale are exquisite. Experience the different facets of the city with guided architecture walks or a river boat tour.

What are the must-see attractions in Chicago?

Chicago: Culture in the Windy City

360 Chicago Observation Deck

What better to way to see the city than from above? Travel up to the 94th floor of the John Hancock Centre for stunning views of the city and over Lake Michigan.

Museum of Science and Industry

At this interactive museum you'll find a life-size replica coal mine and recreated historic Chicago streets with functional shops.

Cloud Gate

One of the most iconic pieces of art in the United States, Cloud Gate was created by Anish Kapoor. This beautiful reflective sculpture is nicknamed 'The Bean' due to its shape.

Millennium Park

This urban park in the centre of Chicago is a great place to wile away an afternoon amidst a tranquil backdrop. Concerts, local fairs and fun events are held regularly at the park.

Art Institute of Chicago

As one of the oldest and largest galleries in the country, this impressive museum showcases over 300,000 artworks. Modern art, photography, ancient sculptures and more feature.

Information about holiday rentals in Chicago

🏡 Holiday homes available 7,999 rentals
💳 Discounts available up to 61%
🌙 Nightly prices from £60
⭐ Popular amenities Pool, Internet and Kitchen
🐾 Pet friendly rentals 3,130 properties
🏊 Holiday rentals with pools 2,732 properties
5,605,515 reviews
Chicago holiday rentals have an average rating of 4.2/5 across 5,605,515 reviews left by travellers.

Frequently Asked Questions

What is a common nightly rate for a holiday home in Chicago?

The average price per night in Chicago is around £60. The nightly rate for apartment rental is £211 on average. House rentals costs around £349 per night.

How many holiday lettings are available to book in Chicago?

July is the time of year with the highest amount of House rentals and Apartment rental available in Chicago, so you'll find plenty of great holiday deals during this month.

What is the most searched holiday home amenity in Chicago?

When looking for a holiday apartment in Chicago, consider looking for a place with Pool, Internet, or Kitchen, which are the most popular amenities for this destination.

How many holiday rentals with a pool there are on offer in Chicago?

Holiday rentals with pools are 34 of all in Chicago on HomeToGo. Also, there are 72 of rentals with pools near water.

What is the perfect time to travel to Chicago?

July and August are the best months for sun lovers in Chicago.

Where can I see discounts on holiday homes in Chicago?

You can find fabulous discounts on holiday accommodation in Chicago with the nightly price of a letting starting at just £60 - and HomeToGo has launched a range of filters that mean it's a piece of cake to locate some awesome offers. When considering different dates for your break, you can use HomeToGo's flexible dates technology to scan for low-price timings and see discounts of up to 61%. Additionally, HomeToGo's 'distance from' filter enables you to discover hidden gem holiday homes in great value, under-the-radar spots with good proximity to your desired destination, whether that's a beach, lake, ski region or city centre. Book early to take advantage of good availability and top discounts - and do so free from stress by using HomeToGo's 'free cancellation' filter when searching for holiday accommodation.

What are the advantages of booking a holiday rental in Chicago with HomeToGo?

From serenity away from the crowds to plenty of room to enjoy with your travel companions, holiday lets in Chicago offer many bonuses. HomeToGo lets you read genuine ratings from verified visitors, and searching is safe, easy, and hassle-free - so with 7,999 offers from 11 providers in the region, you're bound to locate the perfect holiday home with the amenities and features you need in Chicago.

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