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City Breaks in Chicago

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City Breaks in Chicago: Recommended holiday rentals

City Breaks in Chicago: find your perfect rental from just £48 per night!

Bed and breakfast South Austin
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

B&B with 1 room for 2 persons

South Austin, Chicago, Illinois, United States
from £99
per night
from £99
per night
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Bed and breakfast West Woodlawn
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & breakfast with 1 room for 2 persons

West Woodlawn, Chicago, Illinois, United States
from £62
per night
from £62
per night
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Bed and breakfast Illinois Medical District
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Charming bed and breakfast for 2 persons

Illinois Medical District, Chicago, Illinois, United States
from £152
per night
from £152
per night
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Bed and breakfast Bridgeport
Bed and breakfast ∙ 9 guests ∙ 3 bedrooms

Wonderful bed and breakfast with 3 rooms for 9 persons

Bridgeport, Chicago, Illinois, United States
from £227
per night
Outstanding
from £227
per night
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Bed and breakfast University Village / Little Italy
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & breakfast for 2 persons

University Village / Little Italy, Chicago, Illinois, United States
from £172
per night
from £172
per night
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Bed and breakfast Illinois Medical District
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & breakfast for 2 persons

Illinois Medical District, Chicago, Illinois, United States
from £106
per night
from £106
per night
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Bed and breakfast Bucktown
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Family-oriented wonderful bed and breakfast with terrace & garden | Suitable for remote work | Pets are welcome

Bucktown, Chicago, Illinois, United States
from £173
per night
Outstanding(341 ratings)
from £173
per night
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Bed and breakfast Rogers Park
Bed and breakfast ∙ 4 guests ∙ 1 bedroom

Nice bed and breakfast for 4 persons

Rogers Park, Chicago, Illinois, United States
from £66
per night
from £66
per night
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Bed and breakfast Sheffield Neighbors
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Nice bed & breakfast with garden, terrace & barbeque | Good for workation

Sheffield Neighbors, Chicago, Illinois, United States
from £179
per night
Excellent(99 ratings)
from £179
per night
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Bed and breakfast West Woodlawn
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed and breakfast with barbecue, garden & terrace

West Woodlawn, Chicago, Illinois, United States
from £59
per night
Outstanding
from £59
per night
View deal
Bed and breakfast Sheffield & DePaul
Bed and breakfast ∙ 6 guests ∙ 2 bedrooms

B&B with garden, jacuzzi & terrace

Sheffield & DePaul, Chicago, Illinois, United States
from £237
per night
Good
from £237
per night
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Bed and breakfast Rogers Park
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & breakfast with garden

Rogers Park, Chicago, Illinois, United States
from £66
per night
Excellent
from £66
per night
View deal
Bed and breakfast Englewood
Bed and breakfast ∙ 3 guests ∙ 1 bedroom

Bed & breakfast for 3 persons

Englewood, Chicago, Illinois, United States
from £49
per night
from £49
per night
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Bed and breakfast West Ridge
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

B&B with 1 room for 2 persons

West Ridge, Chicago, Illinois, United States
from £114
per night
from £114
per night
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Bed and breakfast West Woodlawn
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

B&B with terrace & garden

West Woodlawn, Chicago, Illinois, United States
from £62
per night
from £62
per night
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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.
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

Bed and breakfast North Center
from £228 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Wonderful B&B with 1 room for 2 persons

North Center, Chicago, Illinois, United States
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Bed and breakfast Sheffield Neighbors
from £160 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

B&B with terrace, BBQ & garden | Suitable for remote work

4.6
Excellent(99 ratings)
Sheffield Neighbors, Chicago, Illinois, United States
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Bed and breakfast Hyde Park
from £108 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed and breakfast with 1 room for 2 persons

Hyde Park, Chicago, Illinois, United States
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Information about City Breaks in Chicago

📏 Average size of a holiday home 72 m²
😎 Quietest month August
🛏️ Popular accommodation types Apartment rental and Bed and breakfast rental
🌡️ Warmest weather 29 °C in July and August
🥶 Coldest weather January and February
🌧️ Rainiest months March and April
54,612 reviews
Chicago holiday rentals have an average rating of 4.4/5 across 54,612 reviews left by travellers.

City Breaks in Chicago: frequently asked questions

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

Vacation homes cost around £48 in Chicago per night.

Can I find holiday rentals for City Breaks in Chicago that can host a family or large group?

When plannin a trip for a big family it's useful to know that average Bed and breakfast rental in Chicago can accommodate 3 guests and costs around £386 per night.

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

You can find more than 5,415 lettings to rent in Chicago with nightly prices starting from £48 per night.

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

There are a lot of options available when it comes to holiday rentals for City Breaks in Chicago, with 59 Bed and breakfast rental and 166 Apartment rental on offer.

Do many accommodations in Chicago offer a pool?

Sure, 33% of lettings in Chicago offer a pool.

More city breaks in Other Great Spots

Check out other holiday accommodation options in Chicago

Check out more holiday options

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