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City Breaks in Chicago

Chicago
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Chicago
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Popular Filters to discover the perfect holiday home in Chicago

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Pets allowed
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Pool
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Cabin

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 South Shore
14 Sept - 21 Sept
£177 per night
Apartment ∙ 8 guests ∙ 3 bedrooms

Flat with 3 Rooms for 8 Persons

5.0
Outstanding
South Shore, Chicago, Illinois, United States
Free cancellation
Details
Agoda
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Resort Archer Heights
4 Oct - 11 Oct
£85 per night
Resort ∙ 127 guests ∙ 1 bedroom

Resort for 127 Persons

3.7
Good
Archer Heights, Chicago, Illinois, United States
Free cancellation
Details
Agoda
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Apartment Tri-Taylor
9 Aug - 16 Aug
£248 per night
Apartment ∙ 6 guests ∙ 2 bedrooms

Lovely Apartment | Suitable for Remote Work | Pet-Friendly

5.0
Outstanding
Tri-Taylor, Chicago, Illinois, United States
Free cancellation
Details
Agoda
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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

Apartment Tri-Taylor
28 Apr - 5 May
-26%
£279
£206 per night
Apartment ∙ 3 guests ∙ 2 bedrooms

Family-Friendly Apartment | Dogs Allowed

5.0
Outstanding (10 ratings)
Tri-Taylor, Chicago, Illinois, United States
Free cancellation
Details
Evolve
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Apartment McKinley Park
26 Oct - 2 Nov
-28%
£180
£130 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Apartment with Garden

McKinley Park, Chicago, Illinois, United States
Free cancellation
Details
Evolve
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Apartment Oak Park
26 Oct - 2 Nov
-30%
£233
£163 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Flat with 2 Rooms for 4 Persons

4.8
Outstanding (4 ratings)
Oak Park, Oak Park Township, Illinois, United States
Free cancellation
Details
Evolve
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Information about City Breaks in Chicago

📏 Average size of a holiday home 86 m²
😎 Quietest month August
🛏️ Popular accommodation types Apartment rental and House rentals
🌡️ Warmest weather 29 °C in July and August
🥶 Coldest weather -8 °C in January and February
🌧️ Rainiest months 9 rainy days in March and April

Frequently Asked Questions

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

Holiday rentals in Chicago are between £186 and £462 per night.

Can I find holiday lettings for City Breaks in Chicago that's suitable for a family or large group?

Apartment rental in Chicago can accommodate 4 people on average, with options for larger and smaller groups.

How many holiday homes are available to book for a weekend in Chicago?

There are more than 9,460 lettings available in Chicago costing upwards of £70 per night.

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

There's plenty of variety available when it comes to holiday rentals for City Breaks in Chicago, with 2,016 Apartment rental and 528 House rentals on offer.

Do many vacation rentals in Chicago offer a pool?

Yes, 25% of holiday homes 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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Find holiday inspiration for your next trip

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