Downtown Chicago lake rentals

We found 60 lake rentals — enter your dates for availability

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

Can I find lakefront holiday homes in Downtown Chicago?
Yes, so get ready for lovely scenery and loads of fun both on and off the water. Whether you're after an intimate cabin retreat or a sprawling house to fill with family and friends, there's a lakefront holiday home in Downtown Chicago that'll float your boat (or kayak):

  • If you want to do some windsurfing or cycling during your visit, "53th Floor Magmile Penthouse - Views" in Near North Side will be a terrific choice.
  • Another excellent choice is "52nd Floor Magmile Penthouse - Views". With fun activities like cycling and sailing nearby, this Near North Side retreat will be ideal if you love being outdoors.

Are there any lake house holiday homes with a private pool in Downtown Chicago?
Lock in a lake house holiday home with a private pool in Downtown Chicago and every day can be a swim day. Having a splashing great time is the top priority at one of these superb escapes:

  • The pool at "Luxury Loyola 3 Bedroom, 2 Bath" will add a whole new level of fun to your lakeside stay. Located in Rogers Park, this holiday property also features a nearby marina and free WiFi.
  • Start the day with a dip in your own pool and then roam around the lake at "Wrigleyville | Chicago Guest House | Not Just A Holiday Holiday home". Located in North Side, an oven and off-street parking options will help make your stay even better.

How can I find the best waterfront cabin holiday homes in Downtown Chicago?
Simply enter your travel dates, then use our filter tool to refine your search by price, location and more. We know that flexibility is important, which is why we also have holiday properties that offer free cancellation. Whether it's a lakeside mansion with room to spare or a charming little place in the woods, we'll help you discover the best waterfront cabin holiday home.
Are there pet-friendly lake house holiday homes in Downtown Chicago?
Give your favourite four-legged pal an amazing outdoor adventure at one of these pet-friendly lake house holiday homes in Downtown Chicago:

  • Whether you have two legs or four, every family member will be warmly welcomed at "Amazing 2b/2ba Condo In Downtown Chicago". This escape in The Loop offers a range of handy amenities, including high-speed internet services and a restaurant dining guide.
  • "The Guild | Mag Mile - Gold Coast 6bd" in Streeterville is another lake house holiday home that'll make your dog howl with joy. A fridge and internet services are among the conveniences available.

Are there any luxury lake holiday houses in Downtown Chicago?
If you've been dreaming about a waterside escape, give the beach a miss and stay at one of these luxury lake houses in Downtown Chicago instead:

  • Boasting lots of style and space for the entire family, "53th Floor Magmile Penthouse - Views" in Near North Side is popular for a good reason. Enjoy perks such as a sauna and a swimming pool in addition to the natural scenes around you.
  • "52nd Floor Magmile Penthouse - Views" in River North is another popular pick. From its tranquil lakeside vibe to its quality amenities such as a swimming pool and beauty services, this is where holiday memories are made.

How can I find cheap lake house holiday homes in Downtown Chicago?
Securing a cheap lake house holiday home on Bookabach is a breeze. Type in your travel details, then use our handy filter tool to narrow your results by price, location and more. Flexibility counts, so you'll be pleased to know that you can seek out properties that also offer free cancellation. Our Book with Confidence Guarantee means you can enjoy a hassle-free holiday with Bookabach.
What are some of the best lake houses to rent for a weekend in Downtown Chicago?
Turn your Friday into a real "Fri-yay!" by leaving work and going somewhere exciting for the weekend. These lake houses in Downtown Chicago are ideal for squeezing in a little R&R by the water:

  • "53th Floor Magmile Penthouse - Views" in Near North Side proves life is just better by the lake. Spend your time making the most of the water and discovering close-by attractions, such as Wrigley Field and McCormick Place.
  • Adventure or relaxation? Whichever you prefer, you'll have loads of both at "52nd Floor Magmile Penthouse - Views" in Near North Side. Take it easy in your cosy lake house or set out and discover Millennium Park and Willis Tower.