Central Chicago Luxury Holidays

Book a Luxury Hotel + Flight or Car together to unlock savings

Photo by Phil Ostroff

  • Plan, book, travel with confidence

  • Better together

    Save up to £250 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Packages with flights are ATOL protected

Top flight + Luxury hotel deals in Central Chicago

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

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was £1,256, price is now £929 per person
£929
per person
9 Jul - 13 Jul
just found
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (3,280 reviews)
Really good spot and location. Staff was super helpful and nice.

Reviewed on 22 Apr 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was £1,327, price is now £982 per person
£982
per person
9 Jul - 13 Jul
just found
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (455 reviews)
Great staff, full kitchen and living room, good location, friendly people, safe. I would stay here again.

Reviewed on 23 Apr 2026

The Rose Chicago, Tapestry Collection by Hilton

The Rose Chicago, Tapestry Collection by Hilton

4 out of 5
Price was £3,256, price is now £2,479 per person
£2,479
per person
8 Jun - 12 Jun
found 24 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Great waist staff loved that the shuttle will take you pretty much anywhere around the Clock 24 hours a day every half hour.

Reviewed on 21 Apr 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was £1,763, price is now £1,379 per person
£1,379
per person
26 May - 30 May
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (932 reviews)
Extremely friendly staff and was able to get an early check-in and an upgraded room. The room itself was everything thats advertised...amazing amenities and a beautiful view from the balcony. There could have been a few dings and scuffs in the room, but it was perfect for my two-day stay and someplace I would come back to again and again

Reviewed on 22 Apr 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was £1,336, price is now £1,075 per person
£1,075
per person
26 May - 30 May
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (2,636 reviews)
The hotel was in great location downtown. The rooms and bedding was also clean and nice. We had to request a room change because the toilet and sink were not working correctly. In the new room, the bathroom sink continued to not drain. It was definitely annoying and disgusting. I probably won’t be staying here again due to the bathroom issue, but overall if that won’t bother you - it’s a good clean hotel with great staff.

Reviewed on 22 Apr 2026

Don't see what you're looking for?
See all available trips from Dublin to Central Chicago
View all trips

5* Luxury holidays in Central Chicago

Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Price was £1,623, price is now £1,426 per person
£1,426
per person
9 Jul - 13 Jul
just found
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,003 reviews)
Beautiful and in walking distance to so many shops and cafes! We had a great stay.

Reviewed on 6 Apr 2026

Don't see what you're looking for?
See all available trips from Dublin to Central Chicago
View all trips

3 Night Luxury holidays in Central Chicago

Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was £1,552, price is now £1,325 per person
£1,325
per person
28 May - 31 May
found 20 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
8.8/10 Excellent! (2,131 reviews)
I have stayed at a few Fairmount properties in the past and I would say this was not my favorite of the brand. Overall a nice hotel but not for the price point.

Reviewed on 20 Apr 2026

Grand Geneva Resort & Spa

Grand Geneva Resort & Spa

4 out of 5
Price was £2,261, price is now £1,918 per person
£1,918
per person
10 Jul - 13 Jul
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
8.6/10 Excellent! (1,004 reviews)
All the hype ended up not so grand of a stay. Beds aren’t comfortable, the club lounge was not worth the money for the food they served and they tack taxes and fees on everything from the resort fees to the club lounge to the rooms. Made the mistake of Easter weekend and were over run with families with small children running around. They have a reward point system that no one tells you about and good luck getting any receipts to submit for it! Highlight of the stay was not part of resort but the best part….was the horse riding trail great staff there and horses are gentle ! Won’t stay here again, unfortunately not worth the money to stay there!

Reviewed on 12 Apr 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was £1,560, price is now £1,335 per person
£1,335
per person
28 May - 31 May
found 20 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (455 reviews)
Great staff, full kitchen and living room, good location, friendly people, safe. I would stay here again.

Reviewed on 23 Apr 2026

Don't see what you're looking for?
See all available trips from London to Central Chicago
View all trips

4 Night Luxury holidays in Central Chicago

Price found within the past 48 hours. Click for updated prices.
Motel 6 Elk Grove Village, IL

Motel 6 Elk Grove Village, IL

2 out of 5
Price was £2,844, price is now £2,049 per person
£2,049
per person
8 Jun - 12 Jun
found 24 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
8.2/10 Very Good! (1,202 reviews)
Very comfortable beds, very clean room. Remodeled shower with great water pressure and lots of hot water.Coffee was great.What a deal

Reviewed on 16 Apr 2026

Motel 6 Glenview, IL - Chicago North

Motel 6 Glenview, IL - Chicago North

2 out of 5
Price was £2,850, price is now £2,059 per person
£2,059
per person
8 Jun - 12 Jun
found 24 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
7.2/10 Good! (1,006 reviews)
Outstanding Service and Property Management.

Reviewed on 15 Mar 2026

Extended Stay America Suites Chicago Elmhurst O'Hare

Extended Stay America Suites Chicago Elmhurst O'Hare

2.5 out of 5
Price was £2,906, price is now £2,100 per person
£2,100
per person
8 Jun - 12 Jun
found 24 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
7.2/10 Good! (1,013 reviews)
Property was clean and affordable.

Reviewed on 11 Apr 2026

Don't see what you're looking for?
See all available trips from Edinburgh to Central Chicago
View all trips

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 £929. 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.

More holidays you might like

All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

* 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.