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City Breaks in Chicago

Chicago
Anytime
Guests
Chicago
Anytime
Guests

Choose the perfect holiday letting

Price per night
Up to £100
£100 - £199
From £200
Distance to center
1 km
2 km
5 km
Rating
4.5+
4+

Planning City Breaks in Chicago

How do you feel about satiating your wanderlust in a world-class destination? City breaks in Chicago, Illinois, offer impressive experiences for families, friends, and even lovers on holiday. From delicious pizza to a rich local culture, there is something for everyone in Chicago.

City Breaks in Chicago: Top Holiday Lettings

Apartment Rush & Division
£185 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Wonderful Holiday Apartment in Rush & Division with Terrace & Barbecue, Close to John Hancock Center

Rush & Division, Chicago, Illinois, United States
Details
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Apartment Heart of Chicago
£207 per night
Apartment ∙ 8 guests ∙ 3 bedrooms

Pleasant Holiday Apartment in Heart Of Chicago with Terrace

Heart of Chicago, Chicago, Illinois, United States
Details
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Apartment Lake View East
3 Aug - 10 Aug
£252 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Holiday Apartment in Lake View East

5.0
Outstanding (8 ratings)
Lake View East, Chicago, Illinois, United States
Details
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Top 5 Things to See: 48Hrs in Chicago

Top 5 Things to See: 48Hrs in Chicago

There are hundreds of sights for holiday-makers to take in in Chicago. However, with a maximum of 48 hours, you deserve only the best destinations. Fortunately, the following spots are a great place to start planning itineraries for short city breaks in Chicago.

  1. Skydeck

    On this Willis Tower ledge, one of the tallest features in the U.S., you can enjoy unparalleled views over the city. In fact, on clear days, you can see at least three other states.

  2. Oak Street at Michigan Avenue

    This street full of boutiques and stores in the posh Gold Coast neighbourhood is a luxury shopper's paradise. Shop the latest fashions and bring home some great souvenirs, or at least window-shop and pose for glamourous selfies.

  3. Revival Food Hall

    Housed in a restored 1907 building, this massive food hall lets you taste an incredible range of delicacies. Sample different cuisines from all over the world and sit down for a cocktail at the on-site bar.

  4. Art Institute of Chicago

    This is one of the largest and oldest museums in the country, housed in a fantastic historic building. Exhibitions range from ancient global art to Pop Art to Bauhaus retrospectives, so there's something for every taste. Be sure to check the exhibition schedule ahead of time.

  5. BP Bridge

    Head to this ribbon-like pedestrian path for a relaxing stroll and a fantastic view of Millennium Park. The bridge itself is an architectural marvel, designed by the acclaimed architect Frank Gehry.

Best Places to Stay for City Breaks in Chicago

House Chatham
3 Aug - 10 Aug
£187 per night
House ∙ 5 guests ∙ 3 bedrooms

Wonderful Holiday Home in Chatham

5.0
Outstanding (6 ratings)
Chatham, Chicago, Illinois, United States
Details
Vrbo
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Apartment Illinois Medical District
3 Aug - 10 Aug
-14%
£253
£218 per night
Apartment ∙ 8 guests ∙ 3 bedrooms

Entire Flat in Illinois Medical District with Private Parking + Scenic Views

4.7
Excellent (57 ratings)
Illinois Medical District, Chicago, Illinois, United States
Details
Vrbo
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Apartment South Chicago
3 Aug - 10 Aug
-6%
£127
£119 per night
Apartment ∙ 6 guests ∙ 2 bedrooms

Wonderful Flat in South Chicago with Terrace

4.5
Excellent (4 ratings)
South Chicago, Chicago, Illinois, United States
Details
Vrbo
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Information about City Breaks in Chicago

😎 Quietest month June
🥳 Busiest month January
🛏️ Popular accommodation types House rentals and Apartment rental
🌡️ Warmest weather July and August
🥶 Coldest weather January and February
🌧️ Rainiest months March and April

Frequently Asked Questions

How many lettings are available to rent for a weekend getaway in Chicago?

You can find more than 9,827 holiday homes for rent in Chicago costing upwards of £57 per night.

What types of holiday lettings are available for City Breaks in Chicago?

Apartment rental and House rentals are the most popular types of holiday rental for City Breaks in Chicago.

City Breaks in Chicago: what's the average price for holiday accommodation?

Holiday lettings in Chicago are between £103 and £458 per night.

Where I can find holiday homes for City Breaks in Chicago that's suitable for a family or large group?

Mostly a Apartment rental is 85 m² and average capacity is 4 guests - ideal for medium-sized groups and families.

Do many vacation rentals in Chicago feature a pool?

Definitely, more than 25% of lettings in Chicago come with a pool.

The Weather in Chicago

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- Rainy days

Average Nightly Rental Prices in Chicago

Click on any bar to see price and availability information

Holiday Letting Price Information in Chicago

Holiday Rental Availability in Chicago

Rental availability information in Chicago

City Breaks in Chicago: Travel tips, inspiration and holiday ideas

City Breaks: Top destinations and popular places to stay

Travel tips, inspiration and ideas for holidays in Chicago

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