Photo by Juan L. Zavala

Summit Holiday Rentals

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Check prices for these dates

In two weeks
16 Jan - 18 Jan
In two months
27 Feb - 1 Mar
In three months
27 Mar - 29 Mar
In four months
24 Apr - 26 Apr

Our top choices for Summit holiday rentals

Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1026)
"My favorite place to stay hands-down"
United States
Michele
The price is S$216
includes taxes & fees
4 Jan - 5 Jan, 2026
Sentral Michigan Avenue
Front of property
Chicago luxury home suites

Chicago luxury home suites

Chicago luxury home suites
2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (4)
"Amazing stay! The location is very central and close to everything. The room was spotless, and the mattress was very comfortable. I really appreciated that the property is pet friendly. I was able to bring my dog along, which made the trip even better. The view was absolutely stunning. The hosts were very responsive and helpful throughout our stay. Highly recommend!"
Canada
Alex
The price is S$198
includes taxes & fees
18 Jan - 19 Jan, 2026
Chicago luxury home suites
Business centre
Kasa River North Chicago

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (182)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Front of property – evening/night
Level Chicago – Old Town

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (406)
"Great location, clean room and friendly staff!"
United States
Scott
Level Chicago – Old Town
Private kitchen
River West, Third Floor Chicago by 747 Lofts

River West, Third Floor Chicago by 747 Lofts

River West, Third Floor Chicago by 747 Lofts
2.0 star property
West Town
9.0 out of 10, Wonderful, (17)
"Loved the space and location "
United States
Caroline
River West, Third Floor Chicago by 747 Lofts
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Summit Hotel Reviews

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

10/10 Excellent
" We took Amtrak so no problems with parking etc."
Charles 2-night trip
Posted 19 hours ago
Silversmith Hotel Chicago Downtown

Frequently asked questions

Can I find holiday rentals in Summit?

Yes, there are holiday rentals close to the most popular sights in Summit, or you can select a more secluded option if you're looking for a relaxing stay. Summit is known for its restaurants and breweries. Make sure you have time to check out the shopping and churches during your trip.

What can I see and do in Summit?

While exploring the area, visit family-friendly sights like Galloping Ghost, or get outside and enjoy nature at Millennium Park. Other popular places to visit in the area include Michigan Avenue and Wrigley Field.

What are holiday rentals like in Summit?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Summit. Holiday rentals feature extras like laundry facilities and kitchens so you'll have everything you need. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from public hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a family trip.