Explore Downtown Chicago Golf Retreats

About Downtown Chicago Vacation Rentals

Explore over 2861 golf accommodation rentals in Downtown Chicago. From luxurious golf villas to cozy golf cabins, golf resorts, and exclusive golf hotels, each offers premium amenities designed for families, groups, and golf enthusiasts. Enjoy exceptional comfort and a one-of-a-kind golf experience with these incredible accommodations. Perfect for tranquil golf escapes, relaxing retreats, or golf-inspired getaways, these properties provide style and comfort in Downtown Chicago.

Looking for last-minute deals or the best offers on golf villas, golf cabins, golf resorts, and other golf retreats? StayAndPlay makes it easy to compare options in Downtown Chicago. Choose from spacious family-friendly stays, charming golf escapes, or luxurious golf retreats tailored for ultimate relaxation and play.

Find spacious family-friendly golf accommodations, golf cottage, or luxurious golf villas—all designed for maximum comfort and convenience during your visit.

On average, golf accommodation rentals in Downtown Chicago offer approximately 742.72 ft² of space, giving you and your group plenty of room to relax and enjoy the stunning golf course surroundings.

The average nightly rate for golf accommodation rentals in Downtown Chicago typically ranges around US $407.

StayAndPlay offers a secure and convenient platform to compare and book the best golf retreats in Downtown Chicago. Explore a wide range of properties at unbeatable rates, and enjoy a unique stay immersed in golf with us.

Show more
Show less

Top Golf Accommodation Types in Downtown Chicago

Type Count
Holiday Apartments1762
Vacation Homes334
B&B3
Cabin Rentals2
Villas1

Use these Quick Filters to Find a Vacation Rental in Downtown Chicago

★ Pro Tip: StayAndPlay simplifies your search for the best golf accommodations from leading vacation rental OTAs like Booking.com and more. Use our Advanced Filter to explore golf villas, cozy golf cabins, golf hotels, and golf resorts. Filter by availability, pricing, cancellation options, and amenities to discover the ideal golf retreat in Downtown Chicago.

Weather in Downtown Chicago, IL

View the weather forecast for Downtown Chicago before booking your Downtown Chicago Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Find Nearby Cabin Rentals in these Cities & Neighborhoods


Chicago 6,368 Properties
Chicago 3,729 Properties
Central Chicago 1,480 Properties
The Loop 620 Properties
Near North Side 580 Properties
River North 345 Properties
West Loop 183 Properties
Streeterville 122 Properties
Rush and Division 67 Properties
West Loop Gate 38 Properties
Gold Coast 38 Properties
Killgubbin 31 Properties

Frequently Asked Questions About Downtown Chicago?

What are the best golf resorts, luxury villas, and vacation rentals in Downtown Chicago?

Looking for a place to stay in Downtown Chicago? Explore these highly-rated golf vacation rentals for a one-of-a-kind golf retreat, where you can relax, unwind, and get ready to play your best game:

How many golf stays with private pools are available in Downtown Chicago?

Find exceptional golf retreats with private pools near Downtown Chicago on StayAndPlay. Relax in serene golf vacation rentals with exclusive pool access and picturesque golf course views. Whether it's a spacious golf villa or a secluded golf cabin, these properties offer the perfect blend of luxury and relaxation, so you can focus on your game.

What are the top-rated golf retreats in Downtown Chicago for family stays?

Searching for a family-friendly golf retreat in Downtown Chicago? Explore these top-rated options, each loved by families and groups who have stayed in Downtown Chicago:

How many StayAndPlay golf vacation rentals are available in Downtown Chicago?

StayAndPlay, as of 2026, features over 2861 unique golf villas, golf hotels, golf resorts, and more in Downtown Chicago. Choose from eco-friendly golf accommodations, golf hotels and golf resorts, with new options added frequently.

By 2026, StayAndPlay has curated over 2861 stunning properties in Downtown Chicago, sourced from trusted platforms. Plan your next golf trip now.

For 2026, StayAndPlay provides access to over 2861 premier golf accommodations in Downtown Chicago. Find your ideal golf-retreat and play your best game with StayAndPlay.

Nearby Neighborhood (16) 

NeighborhoodProperty Count
The Loop Golf Rental Cottages and Golf Getaways in Chicago, Illinois 620
Near North Side Golf Rental Cottages and Golf Getaways in Chicago, Illinois 580
River North Golf Rental Cottages and Golf Getaways in Chicago, Illinois 345
Near West Side Golf Rental Cottages and Golf Getaways in Chicago, Illinois 314
West Town Golf Rental Cottages and Golf Getaways in Chicago, Illinois 310
South Loop Golf Rental Cottages and Golf Getaways in Chicago, Illinois 295
Near South Side Golf Rental Cottages and Golf Getaways in Chicago, Illinois 276
West Loop Golf Rental Cottages and Golf Getaways in Chicago, Illinois 183
Lincoln Park Golf Rental Cottages and Golf Getaways in Chicago, Illinois 127
Streeterville Golf Rental Cottages and Golf Getaways in Chicago, Illinois 122
University Village / Little Italy Golf Rental Cottages and Golf Getaways in Chicago, Illinois 85
River West Golf Rental Cottages and Golf Getaways in Chicago, Illinois 44
Old Town Golf Rental Cottages and Golf Getaways in Chicago, Illinois 40
Gold Coast Golf Rental Cottages and Golf Getaways in Chicago, Illinois 38
Printers Row Golf Rental Cottages and Golf Getaways in Chicago, Illinois 4161
Lakeshore East Golf Rental Cottages and Golf Getaways in Chicago, Illinois 3988

There are 646 hotels in Downtown Chicago 11 resorts, and 2099 rentals

Recently Booked Private Villas, Cabin Resorts, and Rentals Downtown Chicago