Private Vacation Homes in Chicago, the USA

Search & Book Private Vacation Homes with Cryptocurrency or Card

July 2026
Jul 2026
MonTueWedThuFriSatSun
Aug 2026
MonTueWedThuFriSatSun

Thursday 30 July 2026 - Friday 31 July 2026 (1 night)

30 Jul 2026
Thursday
31 Jul 2026
Friday
2 Adults - 0 Child
1 room

Chicago - 7 Private Vacation Homes to Choose From

Find deals where other travellers are staying

See map view

Star Rating

Best Price Guarantee

We guarantee we won't be beaten on price. If you find a cheaper hotel deal on another website after you book with us, we’ll refund the difference!

Learn more

Chicago - 7 Properties found

Most booked in last 6 months
Recommended
Star rating
Price
Top rated by customers
Deals
Lang House Chicago
Lang House Chicago

7421 N. SHERIDAN RD.

Amenities

Exceptional

51 reviews

9.8
3-Level Bucktown Home - Amazing Outdoors & Parking
Windy City Wanderer - Depaul, Train, Wrigley Field

2% giveback on bookings

Create an account or login to unlock these rewards

Chicago Townhome
Chicago Townhome

659 N Carpenter St

Amenities
Lynx606
Lynx606

1817 N Lawndale Ave

Amenities
Bucktown, Urban Luxury and Convenience, Near L Train Stop at Western

Top Picks for Private Vacation Homes in Chicago

Try one of these popular top-rated private vacation homes in Chicago

Lang House Chicago

Chicago, US.
9.8
Exceptional

3-Level Bucktown Home - Amazing Outdoors & Parking

Chicago, US.

Windy City Wanderer - Depaul, Train, Wrigley Field

Chicago, US.

Explore Chicago

Discover new destinations in Chicago and find your next stay!

Bucktown, Urban Luxury and Convenience, Near L Train Stop at Western

Chicago, US.

Chicago Townhome

Chicago, US.

Lynx606

Chicago, US.

Perfect Multi-level Wicker Park Home With Parking! 4 Bedroom Home by Redawning

Chicago, US.
FAQs About Private Vacation Homes in Chicago
The best place is The Langham hotel, known for its luxurious stay.
Destination

Discovering Chicago's Coastal Charm and Urban Wonders

Discover what to do and what to see in Chicago

Welcome to the enchanting city of Chicago, Illinois! Nestled on the shores of Lake Michigan, this vibrant metropolis offers a plethora of attractions and landmarks that are sure to captivate any traveler. One of the must-visit landmarks in Chicago is the iconic Navy Pier. Take a leisurely stroll along the pier, which offers beautiful views of the lake, and indulge in exciting activities such as rides on the Ferris wheel, dining at delicious restaurants, and enjoying live entertainment. For art enthusiasts, a visit to the Art Institute of Chicago is a must. Home to an extensive collection of artworks from around the world, including famous pieces by renowned artists like Monet and Van Gogh, the museum promises a truly immersive cultural experience. No trip to Chicago is complete without witnessing the magnificent architecture that defines the city. Embark on an architectural boat tour along the Chicago River and marvel at the stunning skyline, adorned with the towering skyscrapers designed by architectural giants like Frank Lloyd Wright. Exploring Chicago's vibrant neighborhoods is a delightful adventure in itself. From the trendy shops and eateries in Wicker Park to the historic charm of Old Town, each area offers its own unique atmosphere and charm, waiting to be discovered. When it comes to accommodation, Travala.com offers a selection of private vacation homes in Chicago that provide the perfect retreat after a day of exploring. Relax in the comfort and privacy of your own space, while still being just steps away from the city's most sought-after attractions. To make your booking process hassle-free, Travala.com offers multiple payment options, including credit cards, debit cards, and even cryptocurrencies like Bitcoin. Choose the option that suits you best and book your dream vacation home in Chicago today! Experience the allure of Chicago, from its renowned landmarks to its lively neighborhoods. Start planning your unforgettable trip to the Windy City with Travala.com.

Read more
Inspiration

Where To Go & What To See

Get inspired with travel guides and destination ideas from our blog

Explore Our Travel Guides

  • Travel Planning
  • CRYPTO
  • Travel Destination
  • Accommodation Guides
  • Travel Trends
  • News

FAQs

  • Hotel Bookings
  • Hotel Cancellations & Refunds
  • Partial Payment
  • Best Price Guarantee
  • AVA Smart Program
  • Travel Credits & Promo Credits
  • Discount Vouchers

Hotel Bookings

  • When will I receive my hotel confirmation email?

    icon toggle

    You will receive your accommodation booking confirmation within 24 hours of placing your reservation. We also recommend to check your junk mail or spam folder for your itinerary.

    Please also note that you can always view your booking status online using My Trip on our website or by signing in and selecting My Bookings from the account menu.

    Cryptocurrency payments require a certain number of blockchain confirmations for the booking to proceed. The number of blockchain confirmations required for the most commonly used payment options are as follows:

    • BTC payments: 3 confirmations
    • ETH payments (incl. ERC20): 20 confirmations
    • BNB payments (incl. BEP20): near-instant
    • TRON payments (incl. TRC20): near-instant
  • What is the maximum number of rooms that I can book per booking?

    icon toggle

    You can book up to four rooms per booking. For group bookings that exceed four rooms, please contact our Customer Support Team via [email protected].

  • When will I receive my hotel confirmation email?

    icon toggle

    Hotel reservations are usually confirmed within 60 minutes of booking.

    Once confirmed, your official hotel itinerary will be emailed to you. 

    Where to track booking status

    You can view your booking status via My Trips on our website, or the My Bookings section of your account dashboard.

     

    If you need further assistance, please contact our Customer Support team via Live Chat or email [email protected].

    To help us resolve this quickly, please provide your Order Number and your Transaction Hash / Proof of Payment.

     

  • Why isn't there any hotel availability showing?

    icon toggle

    If our website displays no availability, that unfortunately means we have no available rooms at your chosen property for your preferred dates. Please try updating your search criteria with new dates or filters.

    If your travel arrangements are not flexible and you must stay at this property, please live-chat us or submit a Contact Us form for assistance.

  • My order is expired

    icon toggle

    If your flight, hotel, activity, or car rental booking shows a status of expired after you made a payment, please do not attempt to rebook. Bookings automatically expire if a payment is not fully confirmed within our 10-minute window.

    Why did my booking expire?

    Due to fluctuating product rates and real-time currency or cryptocurrency exchange shifts, we limit the initial reservation window to 10 minutes. The reservation will be marked as expired if a successful payment confirmation is not received before this timer runs out.

    I already sent the payment, what happens next?

    Some payment methods, particularly cryptocurrency transactions, can experience blockchain network delays, exceeding our reservation window. Once the payment is detected, our system will automatically attempt to make the reservation again. 

    What should I do if my booking fails after payment is made?

    Our team will find you another alternative for your booking. If there are no suitable alternative options available, we will refund the amount you paid.

     

    If you haven't receive an email after 60 minutes, please reach out to speak to our Customer Support team via Live Chat or email [email protected].

    To help us resolve this quickly, please provide your Order Number and your Transaction Hash / Proof of Payment.

  • Is there any discount available if I do not have any AVA tokens?

    icon toggle

    Each accommodation and activity booking made on Travala will receive a 2% giveback in the form of AVA tokens. In order to receive this giveback, simply activate your FREE Smart Basic account. The giveback will be credited directly to your wallet after you complete your stay. If you don’t have a Travala account yet, create an account here

  • What should I do if my hotel booking expires or fails after payment is made?

    icon toggle

    Please contact our Customer Support team via chat or email [email protected] and the team will find you another alternative for your booking. If there are no suitable alternative options available, we will refund the amount you paid.

  • How do we determine our hotel sort and filter order?

    icon toggle

    Sort and Filter functions in the search result page support you in finding the best accommodation offers as quickly as possible.

    •  
      •  
        • Sort function at the top of the search page enables you to order accommodation search results according to your preference, such as price, rating, distance, guest recommendation, and other criteria.
        • The Filter function enables you to include or exclude various options to suit your travel needs.

    By default, if you do not use either Sort or Filter function, your search results may be ordered based on two factors:

    •  
      •  
        • The nearest distance to the destination/landmark you searched for
        • Property ratings based on top reviews

    SORT

    •  
      •  
        • Price: sorts your search results based on the property price from high to low and low to high
        • Rating: sorts your search results based on the accommodation star rating from 5 stars to 1 star and 1 star to 5 stars.
        • Distance from downtown: sorts properties nearest to the location you searched for.
        • Property Rank: sorts properties based on transactional data and details about the property.
        • Top Rated: sorts properties with the outstanding ratings based on our data.
        • Guest Recommended: sorts by the percentage of guests who recommend staying at this property. Use this option to get the properties with the highest recommendation score display first.

    FILTER

    •  
      • Search Hotels: filters properties by name once the hotel/property name is entered.
      • Price per night: filters properties by price range once the minimum and maximum price range is selected.
      • Popular Filters: we show the most common filters here that help you easily find the best choice from one or more filters.
      • Star Rating: filters by desired minimum star rating, e.g. only 5-star hotels, both 4-star and 5-star hotels, etc.
      • Guest Review: filters by guest review types, including Excellent, Very Good, etc.
      • Property Type: filters by property types, e.g. Hotel, Villa, Apartment, etc.
      • Amenities: filters by desired amenities, e.g. Swimming Pool, Free WiFi, etc.
      • Hotel Chain: filters by properties that belong to a particular hotel chain.
  • How can I obtain a payment receipt or invoice for my hotel booking?

    icon toggle

    To request a payment receipt or invoice for your hotel booking, please submit a Contact Us request form. Once your request is received we will email you an electronic receipt.

Customer Reviews
What our customers say

Crypto-friendly Bookings

Your money’s good here.

We pride ourselves on being the leading crypto-native travel platform. Pay for your travel anywhere in the world seamlessly using 100+ cryptocurrencies or traditional payments.