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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 £63 per night!

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Bed and breakfast Magnolia Glen
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

B&B with terrace, barbeque & garden | Garden view | Good for workation

Magnolia Glen, Chicago, Illinois, United States
This bed and breakfast in Magnolia Glen features a spa, kitchen, garden, and beach access, perfect for a relaxing getaway.
from £164
per night
Excellent(517 ratings)
from £164
per night
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Bed and breakfast Wicker Park
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed and breakfast with garden

Wicker Park, Chicago, Illinois, United States
Set in vibrant Wicker Park, this bed and breakfast offers a spa, garden, free breakfast, and parking for a perfect getaway.
from £224
per night
Excellent(281 ratings)
from £224
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
This Roscoe Village bed and breakfast features a fireplace, kitchen, and garden, perfect for a family getaway for two.
from £197
per night
Outstanding(115 ratings)
from £197
per night
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Motel Rogers Park
Motel ∙ 2 guests ∙ 1 bedroom

Motel with fast internet | Close to the beach

Rogers Park, Chicago, Illinois, United States
This Rogers Park motel offers convenient parking and a welcoming space for two, perfect for your next getaway.
from £93
per night
Very good(60 ratings)
from £93
per night
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Motel West Woodlawn
Motel ∙ 2 guests ∙ 1 bedroom

Motel for 2 persons

West Woodlawn, Chicago, Illinois, United States
This West Woodlawn motel offers convenient parking and a perfect base for two to explore the vibrant local area.
from £100
per night
from £100
per night
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Motel Washington Heights
Motel ∙ 2 guests ∙ 1 bedroom

Pleasant motel for 2 persons

Washington Heights, Chicago, Illinois, United States
This Washington Heights motel offers convenient parking and a perfect base for exploring vibrant city life with a partner.
from £63
per night
Good(465 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 £92
per night
(1004 ratings)
from £92
per night
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Motel North Park
Motel ∙ 2 guests ∙ 1 bedroom

Wonderful motel for 2 persons

North Park, Chicago, Illinois, United States
This North Park motel features convenient parking and is perfect for a getaway with a companion in a vibrant neighbourhood.
from £69
per night
Good(889 ratings)
from £69
per night
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Motel River North
Motel ∙ 2 guests ∙ 1 bedroom

Pleasant motel | Close to Magnificent Mile

River North, Chicago, Illinois, United States
This River North motel offers beach access, free breakfast, and parking for a perfect getaway for two by the water.
from £121
per night
Excellent(1192 ratings)
from £121
per night
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Motel Peterson Park
Motel ∙ 2 guests ∙ 1 bedroom

Nice motel for 2 persons

Peterson Park, Chicago, Illinois, United States
This motel in Peterson Park offers convenient parking and a perfect base for exploring the scenic beauty of the area.
from £66
per night
(842 ratings)
from £66
per night
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Bed and breakfast East Village
Bed and breakfast ∙ 16 guests ∙ 8 bedrooms

B&B with garden | Perfect for remote work

East Village, Chicago, Illinois, United States
This East Village bed and breakfast features a spa, kitchen, garden, and balcony, perfect for groups of up to 16 guests.
from £3,008
per night
from £3,008
per night
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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
Nestled in Bucktown, this pet-friendly bed and breakfast features a kitchen, spa, garden, and free breakfast for three guests.
from £141
per night
Outstanding(413 ratings)
from £141
per night
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Bed and breakfast Sheffield & DePaul
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

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

Sheffield & DePaul, Chicago, Illinois, United States
This bed and breakfast in Sheffield Neighbors features a fireplace, balcony, garden, and beach access, perfect for a romantic getaway.
from £180
per night
Excellent(123 ratings)
from £180
per night
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Bed and breakfast Old Town
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

B&B with terrace

Old Town, Chicago, Illinois, United States
This bed and breakfast in Old Town offers beach access, a fireplace, and free breakfast, perfect for a romantic getaway.
from £130
per night
Outstanding(545 ratings)
from £130
per night
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Bed and breakfast Fulton Market
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & breakfast for 2 persons

Fulton Market, Chicago, Illinois, United States
This intimate Bed and Breakfast in West Loop offers free breakfast and a perfect setting for an unforgettable wedding getaway.
from £228
per night
Outstanding(212 ratings)
from £228
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 Bucktown
from £148 per night
Bed and breakfast ∙ 5 guests ∙ 1 bedroom

B&B with terrace & garden

4.9
Outstanding(413 ratings)
Bucktown, Chicago, Illinois, United States
View deal
Bed and breakfast Sheffield & DePaul
from £220 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Charming B&B with terrace, BBQ & garden | Perfect for remote work

4.7
Excellent(123 ratings)
Sheffield & DePaul, Chicago, Illinois, United States
View deal
Bed and breakfast Fulton Market
from £229 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Pleasant bed and breakfast for 2 persons

4.9
Outstanding(212 ratings)
Fulton Market, Chicago, Illinois, United States
View deal

Information about City Breaks in Chicago

💳 Highest rates in September
😎 Quietest month September
🛏️ Popular accommodation types Apartment rental and Bed and breakfast rental
🌡️ 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
8,040 reviews
Chicago holiday rentals have an average rating of 4.3/5 across 8,040 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 £63 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 £370 per night.

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

You can find more than 5,669 lettings to rent in Chicago with nightly prices starting from £63 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 50 Bed and breakfast rental and 166 Apartment rental on offer.

Do many accommodations in Chicago offer a pool?

Sure, 31% of lettings in Chicago offer a pool.

The Weather in Chicago

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