The Loop beach rentals

We found 33 beach rentals — enter your dates for availability

Where to?

Dates

Calendar
Flexible dates

September 2025

October 2025

Explore The Loop beach rentals

Kasa Magnificent Mile Chicago

Sleeps 3 · 1 bedroom

Top rated beach rentals - The Loop

Premier Host

Fantastic city base

Gorgeous property in a fantastic location right by restaurants, shopping and the lake front. Tonya was an excellent host and very helpful with any and all questions. Would definitely return!

Debbie H.

Stayed Aug 2022

Premier Host

Best Apartment I’m Chicago

Facing Lake Michigan, with all the major tall buildings in view, this is THEE only place to vacation in Chicago. Jewel Osco supermarket on the ground floor, can be described as UK Marks and Spencer’s plus....... Door staff friendly and great. Apartment surperbly appointed with kitchen and the best appliances. 2 bedrooms ensuite. Just amazing We will definitely return .

Turlough M.

Stayed Dec 2018

Find spaces that suit your style

House

Condo/Apartment

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, pools, gardens and more
More for less
More space, more privacy, more amenities — more value