Heart of Chicago Winter Rentals & Holiday Homes

Discover winter rentals Heart of Chicago - We found 12 exact matches

About Heart of Chicago Winter Rental on SunSkiResorts

Planning a winter vacation in Heart of Chicago? Discover 12 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Heart of Chicago, IL perfect for your seasonal escape. Our listings include private vacation homes, cabins, condos, villas, resorts, and pet-friendly apartments. SunSki's winter vacation homes feature top amenities such as Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.

Winter accommodations in Heart of Chicago start at US $264. The most popular properties in Heart of Chicago include cabins, bungalows, and rental homes. Planning a snowboarding adventure? Explore our snowboard-friendly ski resorts, chalets, and cabins available for short-term or long-term stays. Whether it's a weekend getaway, monthly retreat, or an extended stay, SunSki ensures a memorable winter trip.

To book your winter vacation homes in Heart of Chicago, visit SunSki's filter option, enter your travel dates, narrow down your preferences, and choose from our extensive list of rentals hassle-free. Explore our interactive map to uncover all accommodations in or around Heart of Chicago and unlock incredible deals.

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Frequently Asked Questions About Heart of Chicago Winter Rentals

There are a lot of options in Heart of Chicago. If you plan on staying in the Heart of Chicago area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Heart of Chicago:

The average cost for winter rentals in Heart of Chicago is $264 per night. SunSki has a wide list of great winter places to stay near Heart of Chicago that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage/chalet rentals in Heart of Chicago that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Heart of Chicago on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Heart of Chicago to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 12 private swimming pools or indoor pools accommodations near Heart of Chicago along with other great amenities.

About 12 holiday rentals in Heart of Chicago boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:

Yes, there are many luxury places to stay in Heart of Chicago for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Heart of Chicago with all the best amenities for your next trip.