Far Southwest Side Golf Holidays

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    Packages with flights are ATOL protected

Top flight + Golf hotel deals in Far Southwest Side

Price found within the past 48 hours. Click for updated prices.
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
£1,086
per person
11 Nov - 15 Nov
found 15 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Room was dated and showed signs of hard wear; front desk staff unfriendly; door men never once open the door for us from the street; area around hotel dirty. Shay, the concierge was super nice though and the lobby was attractively decorated.

Reviewed on 4 Oct 2026

The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

Downtown Chicago
£1,431
per person
28 Dec - 2 Jan
found 8 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
The hotel was beautiful, the room was comfortable, and the staff was welcoming and attentive. Everything was clean and well maintained, and the location made it easy to get around the city. Overall, it was a really nice stay and I’d definitely consider coming back.

Reviewed on 24 Sept 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,915
per person
27 Dec - 1 Jan
found 8 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile

Downtown Chicago
£1,167
per person
28 Dec - 2 Jan
found 8 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,643 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
£1,552
per person
1 Dec - 4 Dec
found 1 day ago
Return direct flight included
Newcastle (NCL) to Chicago (ORD)
9.8/10 Exceptional! (1,015 reviews)
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5* Golf holidays in Far Southwest Side

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,410
per person
16 Nov - 20 Nov
found 14 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

Downtown Chicago
£1,431
per person
28 Dec - 2 Jan
found 8 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
The hotel was beautiful, the room was comfortable, and the staff was welcoming and attentive. Everything was clean and well maintained, and the location made it easy to get around the city. Overall, it was a really nice stay and I’d definitely consider coming back.

Reviewed on 24 Sept 2026

The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
£1,552
per person
1 Dec - 4 Dec
found 1 day ago
Return direct flight included
Newcastle (NCL) to Chicago (ORD)
9.8/10 Exceptional! (1,015 reviews)
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3 Night Golf holidays in Far Southwest Side

Price found within the past 48 hours. Click for updated prices.
Kinzie Hotel

Kinzie Hotel

Downtown Chicago
£1,151
per person
1 Dec - 4 Dec
found 1 day ago
Return direct flight included
Newcastle (NCL) to Chicago (ORD)
9.2/10 Wonderful! (2,172 reviews)
All good

Reviewed on 4 Oct 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,349
per person
1 Dec - 4 Dec
found 1 day ago
Return direct flight included
Newcastle (NCL) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
£1,552
per person
1 Dec - 4 Dec
found 1 day ago
Return direct flight included
Newcastle (NCL) to Chicago (ORD)
9.8/10 Exceptional! (1,015 reviews)
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4 Night Golf holidays in Far Southwest Side

Price found within the past 48 hours. Click for updated prices.
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago
£1,013
per person
11 Nov - 15 Nov
found 15 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (3,324 reviews)
Clean sensible hotel. Can’t beat location.

Reviewed on 5 Oct 2026

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
£1,086
per person
11 Nov - 15 Nov
found 15 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Room was dated and showed signs of hard wear; front desk staff unfriendly; door men never once open the door for us from the street; area around hotel dirty. Shay, the concierge was super nice though and the lobby was attractively decorated.

Reviewed on 4 Oct 2026

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

Downtown Chicago
£1,044
per person
11 Nov - 15 Nov
found 15 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,421 reviews)
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Find amazing golf holidays in Far Southwest Side

How can I find the best golf holidays in Far Southwest Side?

Tee off your top golfing holiday in Far Southwest Side by searching for the perfect accommodation on Expedia. Pop in your dates and start looking at your options. You can even check and book flights, too – just don’t forget to include your golf bag as luggage!

Are there cheap golf packages available in Far Southwest Side?

Bundling your accommodation, flights and car hire together is a great way to save money and ensure everything is easily organised. We have stacks of very tempting luxury and cheap golf packages, with those in Far Southwest Side starting from £1,013. Prices and availability are subject to change. Additional terms may apply.

Can I book Far Southwest Side golf and spa packages?

There’s no better way to unwind after a step-heavy day on the course than with a few hours in the spa. Or, for golf-widowed husbands or wives, a golf and spa package holiday could be a winning way to spend some quality time together, with activities to keep everyone happy. Use the spa filter to find golf holidays in Far Southwest Side with that added level of bliss.

How can I find luxury golf holidays in Far Southwest Side?

Score under par on the course and go overboard on everything else with a luxury golf holiday to Far Southwest Side. To find the most special spots, use the 5-star properties filter, and – go on – treat yourself to business class flights.

Can I book all-inclusive golf holidays in Far Southwest Side?

Use the all-inclusive filter to hunt out those glorious all-inclusive golf holidays in Far Southwest Side. If there are none available, consider half board – you’ll likely be out on the golf course at lunchtime anyway.

Why should I book Far Southwest Side golf holidays including flights?

Save money, save time and save paperwork by booking your accommodation, flights and even car hire all with Expedia. It takes just a few clicks to see all the options and book in one fell swoop.

Should I book a last-minute golf holiday in Far Southwest Side?

If you have free time on your side or annual leave to use up, a spontaneous last-minute golf trip in Far Southwest Side is a wonderful idea. Pop in a few dates to see what’s available – you might even save money with last-minute deals.

Can I book a golf holiday in Far Southwest Side with free cancellation and/or flexible dates?

Flexibility is the spice of life, so use our dedicated filter to find accommodation and flights with free cancellation options. Remember, though, always check the small print before booking!

Why should I book my golf trip to Far Southwest Side with Expedia?

Booking a golf trip to Far Southwest Side with Expedia feels like getting a hole-in-one on your first shot on the course. It’s smooth, easy and, with so many options to choose from, you’ll feel giddy with excitement.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£18
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

£32
per adult
88% of travellers recommend
Skydeck Chicago at Willis Tower
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Far Southwest Side

More holidays you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.