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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 £42 per night!

Bed and breakfast Bucktown
Bed and breakfast ∙ 3 guests ∙ 1 bedroom

Bed and breakfast with garden & terrace | Good for workation

Bucktown, Chicago, Illinois, United States
from £144
per night
Outstanding(341 ratings)
from £144
per night
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Bed and breakfast Old Town
Bed and breakfast ∙ 3 guests ∙ 1 bedroom

Bed & breakfast with terrace

Old Town, Chicago, Illinois, United States
from £121
per night
Outstanding
from £121
per night
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Resort Bucktown
Resort ∙ 4 guests ∙ 1 bedroom

Resort with terrace, sauna & hot tub | Suitable for remote work

Bucktown, Chicago, Illinois, United States
from £257
per night
Excellent
from £257
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 £149
per night
Outstanding(341 ratings)
from £149
per night
View deal
Bed and breakfast Canaryville
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & breakfast | Suitable for remote work

Canaryville, Chicago, Illinois, United States
from £42
per night
from £42
per night
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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 £189
per night
Good
from £189
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 £61
per night
from £61
per night
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Bed and breakfast Roscoe Village
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Family-oriented charming B&B with terrace & garden

Roscoe Village, Chicago, Illinois, United States
from £243
per night
Outstanding(110 ratings)
from £243
per night
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Bed and breakfast North Center
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed and breakfast with 1 room for 2 persons

North Center, Chicago, Illinois, United States
from £235
per night
from £235
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 £67
per night
Outstanding
from £67
per night
View deal
Bed and breakfast North Center
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed and breakfast with 1 room for 2 persons

North Center, Chicago, Illinois, United States
from £134
per night
from £134
per night
View deal
Bed and breakfast West Woodlawn
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

B&B with garden & terrace | Good for workation

West Woodlawn, Chicago, Illinois, United States
from £67
per night
from £67
per night
View deal
Bed and breakfast Hyde Park
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed and breakfast with 1 room for 2 persons

Hyde Park, Chicago, Illinois, United States
from £120
per night
from £120
per night
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Bed and breakfast Andersonville
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & breakfast for 2 persons

Andersonville, Chicago, Illinois, United States
from £52
per night
Good
from £52
per night
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Bed and breakfast Back of the Yards
Bed and breakfast ∙ 3 guests ∙ 1 bedroom

B&B with garden | Suitable for remote work

Back of the Yards, Chicago, Illinois, United States
from £41
per night
from £41
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

Motel River North
from £72 per night
Motel ∙ 5 guests ∙ 1 bedroom

Motel | Near Magnificent Mile

4.5
Excellent
River North, Chicago, Illinois, United States
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Bed and breakfast West Loop
from £158 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Pleasant B&B for 2 persons

4.9
Outstanding(166 ratings)
West Loop, Chicago, Illinois, United States
View deal
Motel Edgewater
from £103 per night
Motel ∙ 4 guests ∙ 1 bedroom

Charming motel for 4 persons

3.8
Good
Edgewater, Chicago, Illinois, United States
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Information about City Breaks in Chicago

💳 Highest rates in July
🥳 Busiest month October
🛏️ Popular accommodation types Bed and breakfast rental and Apartment rental
🌡️ Warmest weather 29 °C in July and August
🥶 Coldest weather January and February
🌧️ Rainiest months 9 rainy days in March and April
51,545 reviews
Chicago holiday rentals have an average rating of 4.4/5 across 51,545 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 £42 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 £333 per night.

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

You can find more than 5,524 lettings to rent in Chicago with nightly prices starting from £42 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 55 Bed and breakfast rental and 166 Apartment rental on offer.

Do many accommodations in Chicago offer a pool?

Sure, 32% of lettings in Chicago offer a pool.

The Weather in Chicago

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