Compare Cottages, Resorts, & Rentals in South Loop, Chicago, Illinois, USA
About South Loop Vacation Rentals
There are over 557 amazing vacation rentals available in South Loop. Choose from a variety of options including villas, hotels, and other rental properties. Explore a vast selection of luxury amenities at unbeatable prices, providing you with the ideal spot for your next getaway. Life is Better at the Cottage with Vacation Cottage, where you can discover fantastic stays in South Loop.
Vacation Cottage offers numerous last-minute deals on villas, hotels, and rentals, both near you and across the globe. Whether you need accommodations for a group or event, such as a hotel or vacation rental (including cabins and private luxury villas), let us assist you. With Vacation Cottage in South Loop, you can easily compare options from multiple suppliers with just a click to find the perfect price point, amenities, and style of stay for you. Whether you're seeking group discounts, private pools, hot tubs, pet-friendly options, or spacious master suite bedrooms with open-air showers, you can find it all with Vacation Cottage vacation rentals, resorts, and Airbnb-style properties in South Loop. The average size of places to stay near South Loop is approximately 802.67 ft², with prices averaging US $471 per night.
Vacation Cottage helps you discover the perfect holiday rental to create lasting travel memories in South Loop. Prices listed often feature discounts compared to rack rates. Simply search for your destination and secure your ideal place to stay today.
Find Vacation Cottage Rentals in these Cities and Neighborhoods South Loop, IL
Frequently Asked Questions About South Loop?
What are the top cottages, summer homes, and lake houses in South Loop?
- Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba
- Cozy Downtown MICH AVE #7 | gym+rooftop
- Chic 2-Bedroom Townhouse with Rooftop, Free Parking, in Downtown Chicago!
- Dtown Penthouse 11+Parking, Gym, Pvt Patio
- Downtown 2bd #4 - Near Grant Park, Museums, Lake
- Walkable 2BR Apartment in Chicago South Loop with Optional Parking and Gym Access Near McCormick Place, Museum Campus & Lakefront
- Cozy 2BR South Loop Condo with Optional Parking and Gym Near McCormick Place, Public Transit & City Hotspots
- Spacious 2BR South Loop Suite with Skyline View, Optional Parking and Gym Access Close to McCormick Place, Grant Park, Museum Campus & CTA Lines
- South Loop 2BR Retreat Near Grant Park, Soldier Field & Columbia College
- Spacious 2BR in Chicago Near McCormick Sleeps 8
How many rentals, hotels, or resorts are available in South Loop?
Vacation Cottage consistently updates its selection, offering a blend of new options alongside well-established accommodations in prime locations. Currently, there are over 557 properties listed by Vacation Cottage in the South Loop area for the year 2026, with this number increasing daily. By aggregating listings from various websites and travel providers, Vacation Cottage ensures a diverse array of choices for the best luxury stays in South Loop.
Nearby Neighborhood (7)
| Neighborhood | Property Count |
|---|---|
| Downtown Chicago Rental Cottages and Private Getaways in Chicago, Illinois | 1365 |
| The Loop Rental Cottages and Private Getaways in Chicago, Illinois | 627 |
| Near South Side Rental Cottages and Private Getaways in Chicago, Illinois | 244 |
| Prairie District Rental Cottages and Private Getaways in Chicago, Illinois | 184 |
| Printers Row Rental Cottages and Private Getaways in Chicago, Illinois | 4166 |
| Ickes Praire Homes Rental Cottages and Private Getaways in Chicago, Illinois | 2101 |
| Chicago Museum Campus Rental Cottages and Private Getaways in Chicago, Illinois | 3309 |
