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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 £60 per night!

Bed and breakfast Wicker Park
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed and breakfast with garden

Wicker Park, Chicago, Illinois, United States
Nestled in Wicker Park, this bed and breakfast offers a spa, free breakfast, garden, and parking for a perfect getaway.
from £203
per night
Excellent(242 ratings)
from £203
per night
View deal
Bed and breakfast Magnolia Glen
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed and breakfast with barbeque, terrace & garden | Garden view | Perfect for remote work

Magnolia Glen, Chicago, Illinois, United States
Set in Magnolia Glen, this bed and breakfast offers beach access, a spa, and a garden with a balcony for ultimate relaxation.
from £191
per night
Excellent(472 ratings)
from £191
per night
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Motel Edgewater
Motel ∙ 10 guests ∙ 1 bedroom

Motel for 10 persons

Edgewater, Chicago, Illinois, United States
This Edgewater motel features convenient parking and accommodates up to 10 guests, perfect for your next getaway.
from £95
per night
from £95
per night
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Bed and breakfast Sheffield & DePaul
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

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

Sheffield & DePaul, Chicago, Illinois, United States
This bed and breakfast in Sheffield Neighbors features a fireplace, balcony, and beach access, perfect for a romantic getaway.
from £232
per night
Excellent(100 ratings)
from £232
per night
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Bed and breakfast Fulton Market
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Pleasant bed and breakfast for 2 persons

Fulton Market, Chicago, Illinois, United States
This West Loop bed and breakfast offers a perfect spot for couples, featuring free breakfast and an ideal setting for weddings.
from £284
per night
Outstanding(171 ratings)
from £284
per night
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Bed and breakfast Old Town
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & breakfast with terrace | City view

Old Town, Chicago, Illinois, United States
This bed and breakfast in Old Town offers beach access, a balcony, a fireplace, and free breakfast for a perfect getaway.
from £152
per night
Outstanding(452 ratings)
from £152
per night
View deal
Motel Rogers Park
Motel ∙ 2 guests ∙ 1 bedroom

Motel with fast internet | Close to the beach

Rogers Park, Chicago, Illinois, United States
This motel in Rogers Park offers convenient parking and a perfect base for couples to explore the vibrant local scene.
from £99
per night
Good(540 ratings)
from £99
per night
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Motel North Park
Motel ∙ 2 guests ∙ 1 bedroom

Motel for 2 persons

North Park, Chicago, Illinois, United States
This North Park motel offers convenient parking and a perfect base for couples seeking adventure in the vibrant local area.
from £69
per night
Good(636 ratings)
from £69
per night
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Resort Bucktown
Resort ∙ 10 guests ∙ 1 bedroom

Pleasant resort with sauna, terrace & heated pool

Bucktown, Chicago, Illinois, United States
This Bucktown resort offers a heated pool, spa, and wellness facilities, perfect for gatherings of up to 10 guests.
from £205
per night
from £205
per night
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Bed and breakfast Boystown
Bed and breakfast ∙ 10 guests ∙ 1 bedroom

B&B for 10 persons

Boystown, Chicago, Illinois, United States
This Boystown bed and breakfast offers parking and accommodates up to 10 guests for a vibrant getaway in the heart of the city.
from £115
per night
from £115
per night
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Bed and breakfast West Ridge
Bed and breakfast ∙ 3 guests ∙ 2 bedrooms

B&B with 2 rooms for 3 persons

West Ridge, Chicago, Illinois, United States
This Bed and Breakfast rental in West Ridge features a kitchen and parking, perfect for an unforgettable getaway with friends.
from £54
per night
from £54
per night
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Motel River North
Motel ∙ 4 guests ∙ 1 bedroom

Motel | Near Magnificent Mile

River North, Chicago, Illinois, United States
This River North motel offers beach access, free breakfast, parking, and a balcony for a perfect getaway for four.
from £114
per night
Very good(1001 ratings)
from £114
per night
View deal
Motel Peterson Park
Motel ∙ 2 guests ∙ 1 bedroom

Motel for 2 persons

Peterson Park, Chicago, Illinois, United States
Set in Peterson Park, this motel offers convenient parking and a perfect base for exploring the area's natural beauty.
from £63
per night
(634 ratings)
from £63
per night
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Motel Archer Heights
Motel ∙ 2 guests ∙ 1 bedroom

Motel for 2 persons

Archer Heights, Chicago, Illinois, United States
This motel in Archer Heights features a fireplace, free breakfast, and parking, perfect for a memorable getaway for two.
from £94
per night
(1000 ratings)
from £94
per night
View deal
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
This Roscoe Village bed and breakfast features a fireplace, kitchen, and garden, perfect for a family getaway for two.
from £237
per night
Outstanding(110 ratings)
from £237
per night
View deal

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 Bucktown
from £162 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

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

4.9
Outstanding(349 ratings)
Bucktown, Chicago, Illinois, United States
View deal
Bed and breakfast Old Town
from £203 per night
Bed and breakfast ∙ 10 guests ∙ 1 bedroom

Bed & breakfast with terrace | City view

4.9
Outstanding(452 ratings)
Old Town, Chicago, Illinois, United States
View deal
Bed and breakfast Wicker Park
from £176 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed and breakfast with garden

4.5
Excellent(242 ratings)
Wicker Park, Chicago, Illinois, United States
View deal

Information about City Breaks in Chicago

📏 Average size of a holiday home 68 m²
🥳 Busiest month January
🛏️ 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

City Breaks in Chicago: frequently asked questions

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

Vacation homes cost around £60 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 4 guests and costs around £413 per night.

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

You can find more than 5,678 lettings to rent in Chicago with nightly prices starting from £60 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 54 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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