Far Southwest Side Luxury Holidays

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Top flight + Luxury hotel deals in Far Southwest Side

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
£729
per person
7 Nov - 12 Nov
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (512 reviews)
Beautiful property in great location! Would have definitely been a 5 but rooms facing the pool was very noisy

Reviewed on 19 Aug 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
£1,159
per person
7 Nov - 12 Nov
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
A+

Reviewed on 20 Aug 2026

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
Save 100% on your flight
£931
per person
7 Nov - 12 Nov
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
Save 100% on your flight
£940
per person
7 Nov - 12 Nov
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Beautiful room & View!! Will definitely book again!

Reviewed on 19 Aug 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£773
per person
7 Nov - 12 Nov
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Very pricey but then again its downtown Chicago. Excellent breakfast buffet, very roomy shower and entire bathroom. Comfortable bed, needs better pillows, very secure.

Reviewed on 20 Aug 2026

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5* Luxury 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
Save 100% on your flight
£1,159
per person
7 Nov - 12 Nov
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
A+

Reviewed on 20 Aug 2026

Park Hyatt Chicago

Park Hyatt Chicago

Downtown Chicago
Save 100% on your flight
£1,501
per person
7 Nov - 12 Nov
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
Save 100% on your flight
£3,409
per person
20 Sept - 25 Sept
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Stayed for a weekend trip. Staff were extremely attentive and knowledgeable about the property and city in general. Room arrangement and amenities were excellent. Pool was larger than expected for a ‘high rise’ pool, and very family friendly - towels/locker room was well stocked. Location in relation to city is perfect for shopping and local excursions, but would recommend uber/lift to get around

Reviewed on 16 Aug 2026

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3 Night Luxury holidays in Far Southwest Side

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
£1,081
per person
7 Oct - 10 Oct
found 22 hours ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Beautiful room & View!! Will definitely book again!

Reviewed on 19 Aug 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£1,222
per person
22 Oct - 25 Oct
found 10 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Very pricey but then again its downtown Chicago. Excellent breakfast buffet, very roomy shower and entire bathroom. Comfortable bed, needs better pillows, very secure.

Reviewed on 20 Aug 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
£1,247
per person
7 Oct - 10 Oct
found 22 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,638 reviews)
Great

Reviewed on 20 Aug 2026

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4 Night Luxury holidays in Far Southwest Side

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
£873
per person
3 Oct - 7 Oct
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
8.2/10 Very good! (2,899 reviews)
Great staff, very clean property. Enjoyed the café for lattes and cocktails! Breakfast is a fair price for being additional. I loved the location many bars and restaurants just a few minutes walk away.

Reviewed on 19 Aug 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£1,133
per person
3 Oct - 7 Oct
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Very pricey but then again its downtown Chicago. Excellent breakfast buffet, very roomy shower and entire bathroom. Comfortable bed, needs better pillows, very secure.

Reviewed on 20 Aug 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
£1,026
per person
3 Oct - 7 Oct
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
The property was wonderful and the proximity to Fulton Market can't be beat. The staff were always helpful when we had questions and when I faced an unexpected event they were understanding and accommodating. If you are looking for a space where you can spread out, be outdoors, and have beautiful surroundings, I highly recommend Level Fulton Market. We loved the pool and variety of outdoor spaces as well as lounge areas that allowed our group to have separate hang out areas. While you are of course in the heart of the city, the noise fell to the background and we had no issues sleeping or feeling rested. Everything was comfortable and clean. Easy walking to the best dining in the city.

Reviewed on 17 Aug 2026

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All you need to know about luxury holidays in Far Southwest Side

What can I expect from a luxury Far Southwest Side holiday?

Luxury on holiday is all about relaxing and feeling good. Whether you choose a sumptuous spa, Michelin-starred restaurant or super-king bed is your call. Use our amenities filters to find the things that tick all your boxes.

How can I find all-inclusive luxury holidays in Far Southwest Side?

Tick the all-inclusive and 5-star filters to find the crème de la crème of Far Southwest Side holidays. With everything included in the package price, you can drink and dine to your heart’s content, without worrying about that bill at the end.

Can I book a cheap luxury holiday to Far Southwest Side?

A luxury holiday doesn’t have to break the bank. Travel out of peak season, choose a hotel or resort a little way out or go for a last-minute getaway and you’ll find some cracking deals. Sort by price to find luxury holidays to Far Southwest Side starting at £729. Prices and availability are subject to change. Additional terms may apply.

Are there luxury spa holidays in Far Southwest Side?

For sunset massages on the shoreline and view-filled saunas, use our spa filter to find your ideal Far Southwest Side spa hotel. Book a whole weekend soaking away your stresses, or hop into the spa after the beach, some golf or a local advent-ahhhh.

What should I look for when booking a luxury family holiday in Far Southwest Side?

Luxury isn’t just for adults. Those little touches designed for little people make a family holiday genuinely stress free … which is the greatest luxury of all. Look for spacious suites, pools toddlers can splash in, and breakfast buffets with waffles, pancakes and Nutella galore.

Can I book luxury last-minute holidays to Far Southwest Side?

You can wangle a top-notch luxury holiday in Far Southwest Side for a fraction of the normal price by booking last minute. Just enter your dates and see what’s available – if you’re flexible ... even better!

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

If you’re splashing out on a luxury holiday, make sure your money is safe by booking with free cancellation. Just use the fully refundable filter and make sure you read all the terms and conditions.

Why should I book my luxury travel to Far Southwest Side with Expedia?

Nobody does luxury quite like Expedia. With so many gorgeous properties in Far Southwest Side to choose from, as well as access to first-class flight deals and hire cars with horsepower, there’s no better place to book.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

£35
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£18
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Far Southwest Side

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* 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.