Central Chicago Luxury Holidays

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Top flight + Luxury hotel deals in Central Chicago

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

The Emily Hotel

Downtown Chicago
£619
per person
25 Nov - 30 Nov
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,338 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
£1,276
per person
26 Nov - 3 Dec
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
£1,695
per person
26 Nov - 3 Dec
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
My Labor Day weekend stay at Trump International Hotel & Tower Chicago was exceptional in every regard, marked by refined service, remarkable amenities, and a level of hospitality that felt both genuine and elevated. From the moment I arrived, the staff set a distinguished tone, greeting me with champagne and ensuring every detail of my visit was handled with care. The concierge team was attentive and polished, and throughout my stay I felt consistently supported by a standard of service that exceeded expectations. Room 2791 offered a breathtaking view of the city, with floor‑to‑ceiling windows framing Chicago’s skyline in a way that felt both serene and spectacular. The terrace added an unforgettable dimension, providing a private space to enjoy the city’s energy from above while still feeling completely at ease. Room service was prompt, beautifully prepared, and consistently excellent, enhancing the comfort of the stay. The spa and wellness facilities were equally impressive. Ashanti, Christian, and Byron delivered warm, professional service that made each visit feel personal, and my massage therapist provided a treatment that was both restorative and skillfully executed. The sauna, steam room, and gym were immaculate, calming, and thoughtfully maintained, offering a perfect balance of relaxation and rejuvenation. Pablo also stood out for his gracious and attentive service. This stay left a lasting impression, and I will be making Trump Hotels a part of future travels.✨

Reviewed on 18 Sept 2026

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago
£1,095
per person
26 Nov - 3 Dec
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
8.6/10 Excellent! (1,011 reviews)
There were a couple of things about this hotel that threw me for a loop (no in room coffee machine -- but plenty of coffee at the bar with choice of skim, half and half and cream; you first encounter the bar versus the registration area), but I would definitely stay here again, and for that I compliment the staff. Fatima greeted us at check in and immediately noticed my daughter had mobility issues and offered to change our room for an accessible one. Since this was my first overnight trip with my daughter I hadn't even thought of that! I appreciated that she saw a way to make our stay better and made it happen. Fatima also always had a smile on her face when we saw her and was always ready to answer any question. I didn't get the name of the doorman we interacted with the most (but I did get a photo with him!), which I regret. He was an older many who worked day shift and he touched my heart when he stayed by my daughter while I went to get our car from the parking garage. He didn't have to do that. The people definitely made this staff wonderful!

Reviewed on 18 Sept 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
£981
per person
26 Nov - 3 Dec
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (165 reviews)
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5* Luxury holidays in Central Chicago

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
£1,695
per person
26 Nov - 3 Dec
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
My Labor Day weekend stay at Trump International Hotel & Tower Chicago was exceptional in every regard, marked by refined service, remarkable amenities, and a level of hospitality that felt both genuine and elevated. From the moment I arrived, the staff set a distinguished tone, greeting me with champagne and ensuring every detail of my visit was handled with care. The concierge team was attentive and polished, and throughout my stay I felt consistently supported by a standard of service that exceeded expectations. Room 2791 offered a breathtaking view of the city, with floor‑to‑ceiling windows framing Chicago’s skyline in a way that felt both serene and spectacular. The terrace added an unforgettable dimension, providing a private space to enjoy the city’s energy from above while still feeling completely at ease. Room service was prompt, beautifully prepared, and consistently excellent, enhancing the comfort of the stay. The spa and wellness facilities were equally impressive. Ashanti, Christian, and Byron delivered warm, professional service that made each visit feel personal, and my massage therapist provided a treatment that was both restorative and skillfully executed. The sauna, steam room, and gym were immaculate, calming, and thoughtfully maintained, offering a perfect balance of relaxation and rejuvenation. Pablo also stood out for his gracious and attentive service. This stay left a lasting impression, and I will be making Trump Hotels a part of future travels.✨

Reviewed on 18 Sept 2026

The Langham, Chicago

The Langham, Chicago

Downtown Chicago
£2,899
per person
12 Nov - 16 Nov
found 20 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.8/10 Exceptional! (1,004 reviews)
Nobu Hotel Chicago

Nobu Hotel Chicago

Downtown Chicago
£2,520
per person
12 Nov - 16 Nov
found 20 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (922 reviews)
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3 Night Luxury holidays in Central Chicago

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£941
per person
12 Nov - 15 Nov
just found
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,095
per person
12 Nov - 15 Nov
just found
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
My Labor Day weekend stay at Trump International Hotel & Tower Chicago was exceptional in every regard, marked by refined service, remarkable amenities, and a level of hospitality that felt both genuine and elevated. From the moment I arrived, the staff set a distinguished tone, greeting me with champagne and ensuring every detail of my visit was handled with care. The concierge team was attentive and polished, and throughout my stay I felt consistently supported by a standard of service that exceeded expectations. Room 2791 offered a breathtaking view of the city, with floor‑to‑ceiling windows framing Chicago’s skyline in a way that felt both serene and spectacular. The terrace added an unforgettable dimension, providing a private space to enjoy the city’s energy from above while still feeling completely at ease. Room service was prompt, beautifully prepared, and consistently excellent, enhancing the comfort of the stay. The spa and wellness facilities were equally impressive. Ashanti, Christian, and Byron delivered warm, professional service that made each visit feel personal, and my massage therapist provided a treatment that was both restorative and skillfully executed. The sauna, steam room, and gym were immaculate, calming, and thoughtfully maintained, offering a perfect balance of relaxation and rejuvenation. Pablo also stood out for his gracious and attentive service. This stay left a lasting impression, and I will be making Trump Hotels a part of future travels.✨

Reviewed on 18 Sept 2026

Pendry Chicago

Pendry Chicago

Downtown Chicago
£993
per person
12 Nov - 15 Nov
just found
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,146 reviews)
Don't see what you're looking for?
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4 Night Luxury holidays in Central Chicago

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£2,026
per person
12 Nov - 16 Nov
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
£2,409
per person
12 Nov - 16 Nov
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (3,512 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£2,250
per person
12 Nov - 16 Nov
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
My Labor Day weekend stay at Trump International Hotel & Tower Chicago was exceptional in every regard, marked by refined service, remarkable amenities, and a level of hospitality that felt both genuine and elevated. From the moment I arrived, the staff set a distinguished tone, greeting me with champagne and ensuring every detail of my visit was handled with care. The concierge team was attentive and polished, and throughout my stay I felt consistently supported by a standard of service that exceeded expectations. Room 2791 offered a breathtaking view of the city, with floor‑to‑ceiling windows framing Chicago’s skyline in a way that felt both serene and spectacular. The terrace added an unforgettable dimension, providing a private space to enjoy the city’s energy from above while still feeling completely at ease. Room service was prompt, beautifully prepared, and consistently excellent, enhancing the comfort of the stay. The spa and wellness facilities were equally impressive. Ashanti, Christian, and Byron delivered warm, professional service that made each visit feel personal, and my massage therapist provided a treatment that was both restorative and skillfully executed. The sauna, steam room, and gym were immaculate, calming, and thoughtfully maintained, offering a perfect balance of relaxation and rejuvenation. Pablo also stood out for his gracious and attentive service. This stay left a lasting impression, and I will be making Trump Hotels a part of future travels.✨

Reviewed on 18 Sept 2026

Don't see what you're looking for?
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All you need to know about luxury holidays in Central Chicago

What can I expect from a luxury Central Chicago 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 Central Chicago?

Tick the all-inclusive and 5-star filters to find the crème de la crème of Central Chicago 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 Central Chicago?

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 Central Chicago starting at £619. Prices and availability are subject to change. Additional terms may apply.

Are there luxury spa holidays in Central Chicago?

For sunset massages on the shoreline and view-filled saunas, use our spa filter to find your ideal Central Chicago 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 Central Chicago?

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 Central Chicago?

You can wangle a top-notch luxury holiday in Central Chicago 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 Central Chicago 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 Central Chicago with Expedia?

Nobody does luxury quite like Expedia. With so many gorgeous properties in Central Chicago 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 Central Chicago

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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.