Holiday Homes in Chicago, IL

Search among 135 available holiday homes in Chicago from 50+ providers.

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8 adults
3 bedrooms
5 beds
Map
7.9 km from City Centre500 m from Viaduct Center
From£ 129 /nightSelect
Couture Themed 3 Bedroom In Prime Spot With Patio, Parking, Fireplace, Pets WelcomeVilla
8.8
Great18 reviews
10 adults
3 bedrooms
3 beds
Map
3.4 km from City Centre1.7 km from Michigan Avenue
The 3 Bedroom In Best Location Parking Fireplace Patio Home Office Pets Welcome Chicago is situated in the Old Town district, 22 minutes' drive from Midway International airport.
From£ 549 /nightSelect
Huge Lakeview Retreat Sleeping 20 With Parking!Villa
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7.1 km from City Centre1.1 km from Wrigley Field
From£ 393 /nightSelect
Spacious Wicker Park Hideaway With Parking!Villa
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4.5 km from City Centre
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Spacious Bucktown SanctuaryVilla
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5.7 km from City Centre
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Bright Chicago Home With Backyard Less Than 5 Mi To DowntownVilla
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5.2 km from City Centre
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Historical 5 Bedroom Villa That Sleeps 12 Guests With Patio, Fireplace, Grill And Free ParkingVilla
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4.5 km from City Centre
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Spacious Chicago Home With Deck About 3 Mi To Downtown!Villa
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3.3 km from City Centre400 m from United Center
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Tranquil Urban RetreatVilla
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19.1 km from City Centre400 m from Mark Llc
From£ 202 /nightSelect
Chic Chicago Retreat HomeVilla
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6.2 km from City Centre900 m from Saint Augustine College
From£ 224 /nightSelect
Belmont Heights OasisVilla
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15.9 km from City Centre
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Upscale Penthouse Private BalconyVilla
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3.5 km from City Centre1.9 km from United Center
From£ 278 /nightSelect
River North Hideaway With Amazing Views And ParkingVilla
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2.2 km from City Centre400 m from Michigan Avenue
From£ 529 /nightSelect
Old Town Pied-A-Terre With Private Terrace And Parking!Villa
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3.7 km from City Centre1.8 km from Michigan Avenue
From£ 569 /nightSelect
Modern Sfh Near Mccormick Place & Soldier FieldVilla
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1.9 km from City Centre400 m from Pilsen
From£ 778 /nightSelect
Logan Square HideawayVilla
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7.8 km from City Centre
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Hidden East Village GemVilla
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3.4 km from City Centre1.9 km from United Center
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Elegant Hideaway In The Heart Of AndersonvilleVilla
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11.3 km from City Centre
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Suite 1 On Southport 4 Queen BedsVilla
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6.0 km from City Centre
From£ 111 /nightSelect
Spacious Ukrainian Village RetreatVilla
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4.1 km from City Centre1.7 km from United Center
From£ 244 /nightSelect
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FAQs about holiday houses in Chicago

In these 8 answers, you will find our recommendations about different holiday houses in Chicago.

What are the most favoured pet-friendly holiday houses in Chicago?

According to HotelMix.co.uk travel data, there are 15 accommodations that welcome pets. Find out Old Town-Gold Coast Amazing 3 Bedroom Home/ Free Parking/ Breakfast/ Backyard/ Walk Everywhere/ Pets Ok at the cost of 291£ per night, featuring board games, a free carpark and live performances on site. Another great option is The Avondale Guesthouse at the cost of 107£ per one night. Other suitable properties are ✪ Cozy 1 Bedroom Close To Downtown ✪, Wrigleyville Friends Unit - 5Bdrm and Howard Johnson Inn Downtown.

What are the best holiday houses in Chicago with hot tubs?

According to HotelMix.co.uk travel data, there are 8 deals with hot tubs. You may like The Boom Boom Room offering shopping service, a Jacuzzi and complimentary parking at the price of 320£ per one night.

What are the top lakefront holiday houses in Chicago?

One of the top accommodations is Grand Plaza Suites at the cost of 111£ with video games and ironing.

What are the most popular holiday houses among couples in Chicago?

According to HotelMix.co.uk travel data, there are 3 deals for couples. You may find out Pampered Rest Stop - 3 Br, located 2.1 km from Hawthorne Works Museum for 154£ per night.

What are the best holiday houses in Chicago featuring a kitchen?

To enjoy your own meal during a fantastic stay, HotelMix.co.uk offers 3 options to choose from. If you enjoy cooking, book Oakwood 200 Squared with a rating 8.0/10 for 150£ per night, providing an outdoor swimming pool, an indoor swimming pool and a business centre.

What are the cheapest holiday houses in Chicago featuring free parking?

If you want to stay at the place with free parking, HotelMix.co.uk has 10 deals to offer. For instance, Old Town-Gold Coast Amazing 3 Bedroom Home/ Free Parking/ Breakfast/ Backyard/ Walk Everywhere/ Pets Ok, a good choice located 6 km from Wrigley Field. It features board games, a free car park and live performances. Also you may book The Avondale Guesthouse, a top villa with cots, laundry facilities and housekeeping. It costs 107£ per night.

What are the most favoured holiday houses in Chicago not far from Millennium Park?

If you want to stay not far from this tourist destination, HotelMix.co.uk offers you 4 properties to choose from. For instance, book Dch 215 West Washington, a top apartment, which is set a 15-minute walk from Millennium Park. Also you may book Oakwood 200 Squared (rating: 8.0/10) for 150£ per night. It's set 15 minutes' walk away.

What are the top luxury holiday houses in Chicago?

According to HotelMix.co.uk travel data, one of the top holiday houses is Ginosi Basics Loop Apartel set 650 metres from The Loop. It costs 322£ per night.

Holiday Homes in Chicago essential information

🏨 Holiday Homes in Chicago 135
👛 Lowest price 31 GBP
✍️ Holiday Homes Reviews 18
Guest reviews of hotels in Chicago