Vacation homes in Chicago - Casamundo base64Hash Vacation homes in Chicago - Casamundo

Vacation homes in Chicago

Anytime
Guests
Anytime
Guests
15 accommodations available

  • Price per night

    • Up to €100
    • €100 - €199
    • From €200

  • Distance to center

    • 2 mi
    • 3 mi
    • Any

  • Rating

    • 4.5+
    • 4+

  • Services

    • WiFi
    • Kitchen
    • TV
    • Air conditioning
    • Washing machine
    • Microwave
    • Dishwasher

  • Accommodation type

    • Pet-friendly
    • No smoking
    • No pets
    • Wheelchair access

Top 15 most Recommended Vacation Rentals in Chicago

Discover your ideal Chicago vacation rental with real-time comparisons of 15 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

Bed and breakfast Sheffield Neighbors
Bed and breakfast ∙ 2 guests
Sheffield Neighbors, Chicago, Illinois, United States
This delightful bed and breakfast in Sheffield Neighbors offers a fireplace, kitchen, free breakfast, and beach access. Perfect for a romantic getaway or a wedding celebr...
from €206
per night
Excellent(99 ratings)
from €206
per night
Check prices
Bed and breakfast Sheffield Neighbors
Bed and breakfast ∙ 4 guests
Sheffield Neighbors, Chicago, Illinois, United States
This delightful bed and breakfast in Sheffield Neighbors accommodates up to four guests, featuring a cozy fireplace, a fully equipped kitchen, free breakfast, and beautif...
from €287
per night
Excellent(99 ratings)
from €287
per night
Check prices
Bed and breakfast Old Town
Bed and breakfast ∙ 3 guests
Old Town, Chicago, Illinois, United States
Experience a delightful stay at this Old Town bed and breakfast, featuring a cozy fireplace, beautiful balcony, free breakfast, convenient parking, and easy beach access ...
from €157
per night
Outstanding(444 ratings)
from €157
per night
Check prices
Bed and breakfast Sheffield Neighbors
Bed and breakfast ∙ 2 guests
Sheffield Neighbors, Chicago, Illinois, United States
Experience a delightful bed and breakfast rental in Sheffield Neighbors, featuring a cozy fireplace, kitchen, and balcony. Enjoy free breakfast, beach access, and a beaut...
from €207
per night
Excellent(99 ratings)
from €207
per night
Check prices
Bed and breakfast Wicker Park
Bed and breakfast ∙ 2 guests
Wicker Park, Chicago, Illinois, United States
Nestled in vibrant Wicker Park, this inviting bed and breakfast offers a rejuvenating spa, complimentary breakfast, and serene yard space, perfect for a relaxing getaway ...
from €198
per night
Excellent(240 ratings)
from €198
per night
Check prices
Bed and breakfast Wicker Park
Bed and breakfast ∙ 2 guests
Wicker Park, Chicago, Illinois, United States
This delightful bed and breakfast in Wicker Park offers a serene spa, a lovely yard, and free breakfast, providing the perfect retreat for two. Enjoy convenient parking a...
from €187
per night
Excellent(240 ratings)
from €187
per night
Check prices
Bed and breakfast Wicker Park
Bed and breakfast ∙ 2 guests
Wicker Park, Chicago, Illinois, United States
Experience a delightful stay at this Wicker Park bed and breakfast, featuring a relaxing spa, free breakfast, a lovely yard, and convenient parking, perfect for a romanti...
from €187
per night
Excellent(240 ratings)
from €187
per night
Check prices
Bed and breakfast Wicker Park
Bed and breakfast ∙ 2 guests
Wicker Park, Chicago, Illinois, United States
Experience a delightful stay at this Wicker Park bed and breakfast, featuring a relaxing spa, complimentary breakfast, beautiful yard, and convenient parking for a perfec...
from €198
per night
Excellent(240 ratings)
from €198
per night
Check prices
Bed and breakfast Sheffield Neighbors
Bed and breakfast ∙ 5 guests
Sheffield Neighbors, Chicago, Illinois, United States
This inviting bed and breakfast in Sheffield Neighbors offers a fireplace, kitchen, free breakfast, and beautiful yard, perfect for weddings. Enjoy beach access and a bal...
from €264
per night
Excellent(99 ratings)
from €264
per night
Check prices
Bed and breakfast Wicker Park
Bed and breakfast ∙ 4 guests
Wicker Park, Chicago, Illinois, United States
Experience a delightful bed and breakfast in Wicker Park, accommodating up to four guests. Enjoy free breakfast, a relaxing spa, a fully equipped kitchen, a yard, and con...
from €248
per night
Excellent(240 ratings)
from €248
per night
Check prices
Bed and breakfast Magnolia Glen
Bed and breakfast ∙ 2 guests
Magnolia Glen, Chicago, Illinois, United States
This delightful bed and breakfast in Magnolia Glen offers a serene escape for two, featuring a spa, kitchen, free breakfast, inviting yard, balcony, parking, and beach ac...
from €165
per night
Excellent(472 ratings)
from €165
per night
Check prices
Bed and breakfast Wicker Park
Bed and breakfast ∙ 2 guests
Wicker Park, Chicago, Illinois, United States
Experience a delightful stay in Wicker Park at this inviting bed and breakfast featuring a relaxing spa, complimentary breakfast, a beautiful yard, and convenient parking...
from €221
per night
Excellent(240 ratings)
from €221
per night
Check prices
Bed and breakfast Old Town
Bed and breakfast ∙ 2 guests
Old Town, Chicago, Illinois, United States
This inviting bed and breakfast in Old Town features a cozy fireplace, private balcony, and beach access, perfect for a romantic getaway for two. Enjoy complimentary brea...
from €131
per night
Outstanding(444 ratings)
from €131
per night
Check prices
Bed and breakfast Wicker Park
Bed and breakfast ∙ 2 guests
Wicker Park, Chicago, Illinois, United States
This delightful bed and breakfast in Wicker Park offers a serene spa, complimentary breakfast, a spacious yard, and convenient parking, making it the perfect getaway for ...
from €221
per night
Excellent(240 ratings)
from €221
per night
Check prices
House Oak Park
139 m² house ∙ 9 guests ∙ 3 bedrooms
Oak Park, Oak Park Township, Illinois, United States
This spacious house in Oak Park accommodates up to 9 guests and features a family-friendly environment with a kitchen, yard, parking, and pet-friendly options. Perfect fo...
from €261
per night
Very good(5 ratings)
from €261
per night
Check prices

Vacation rentals and apartments with air conditioning

Cool comfort in Chicago: Choose a vacation rental with air conditioning - book your stay!

Bed and breakfast Wicker Park
from €224 per night
2 guests ∙ 1 bedroom

Room, 1 King Bed (Concord)

4.5
Excellent(240 ratings)
Wicker Park, Chicago, Illinois, United States
Air conditioning
Check prices
Bed and breakfast Old Town
from €112 per night
2 guests ∙ 1 bedroom

Suite, 1 Queen Bed

4.9
Outstanding(444 ratings)
Old Town, Chicago, Illinois, United States
Air conditioning
Check prices
Bed and breakfast Magnolia Glen
from €673 per night
4 guests ∙ 1 bedroom

Presidential Suite, 1 Bedroom (1st Floor)

4.5
Excellent(472 ratings)
Magnolia Glen, Chicago, Illinois, United States
Air conditioning
Check prices
See all offers

Vacation Rentals with a Patio

Sunset bliss: book your Chicago vacation rental with a private terrace - your relaxation awaits!

Bed and breakfast Magnolia Glen
from €160 per night
2 guests ∙ 1 bedroom

Superior Room (Room 4)

4.5
Excellent(472 ratings)
Magnolia Glen, Chicago, Illinois, United States
Balcony/Patio
Check prices
Bed and breakfast Magnolia Glen
from €136 per night
2 guests ∙ 1 bedroom

Premier Room (Room 1)

4.5
Excellent(472 ratings)
Magnolia Glen, Chicago, Illinois, United States
Balcony/Patio
Check prices
Bed and breakfast Sheffield Neighbors
from €207 per night
2 guests ∙ 1 bedroom

Venetian Suite

4.6
Excellent(99 ratings)
Sheffield Neighbors, Chicago, Illinois, United States
Balcony/Patio
Check prices
Show more offers
3 reviews
3 travelers who stayed in Chicago gave their vacation rental an average rating of 4.3/5 stars.

Frequently asked questions

What are the most popular accommodations in the area?

The most booked accommodations in Chicago are bed and breakfast rental and house rentals. We search from more than 15 accommodations in Chicago to help you find the perfect place to stay during your trip.

How much does it cost to stay the night?

With Casamundo, you will find vacation rentals starting from €134 in Chicago. On average, accommodations in Chicago will have a size of 167 m² (House rentals) and 66 m² (Bed and breakfast rental).

Do you offer pet-friendly bed and breakfast rental in Chicago?

If you are traveling with your pet, we have the perfect solution: Hotel room are the most pet-friendly accommodations in Chicago. On average a pet-friendly rental costs €226 per night.

Do you offer accommodations for traveling with a group?

Yes, we definitely have accommodations for groups in Chicago. On average, the bed and breakfast rental has space for 3 guests.

Find the perfect accommodation to stay in Chicago

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