Diamond Holidays from £1,424
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Top Diamond Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Thompson Chicago, by Hyatt
Downtown Chicago
Price was £1,820, price is now £1,424 per person
£1,424
per person
20 Jun - 25 Jun
found 12 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,361 reviews)
This is our favorite hotel in chicago. Great location and staff. Rooms very comfortable.
Reviewed on 11 May 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was £2,531, price is now £1,804 per person
£1,804
per person
14 Jun - 21 Jun
found 23 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
If you plan on staying in this hotel by all means the view is great, but if you plan on moving your vehicle at all the hotel does not validate In-N-Out parking. You have to pay every time you want to leave and come back. Unlike the normal hotel, La Quinta downtown Chicago validate parking yes it’s $70 but you can drive in and out as many times as you want during your stay. Unlike this hotel.
Reviewed on 8 May 2026
Chicago Marriott Downtown Magnificent Mile
Downtown Chicago
Price was £1,959, price is now £1,506 per person
£1,506
per person
14 Jun - 21 Jun
found 23 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
8.8/10 Excellent! (1,002 reviews)
Breakfast menu was good, staff at the lounge was good. Checking in was not so good, they wanted to charge me $25 to check in 15 minutes before the time. I think it would be better to say the room is not ready yet the saying your room is ready but is not 2 and if you want it now it will be an extra $25. That I think is ridiculous, which took away from my experience.
Reviewed on 11 May 2026
L7 Chicago by LOTTE
Downtown Chicago
Price was £2,162, price is now £1,705 per person
£1,705
per person
14 Jun - 21 Jun
found 23 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (3,985 reviews)
We celebrated my husband's birthday and Laura (or Lauren) was amazing! Super pleasant check in experience, we got aa beautiful room with a magnificent vibes of the Chicago River. We had a dinner at the Korean restaurant on premises, absolutely delicious and interesting. Definitely would recommend this hotel as a romantic getaway, amazing location too.
Reviewed on 12 May 2026
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
Downtown Chicago
Price was £2,922, price is now £2,353 per person
£2,353
per person
14 Jun - 21 Jun
found 23 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
I loved staying here!! Very upscale. Staff was so nice. I can’t wait to go back.
Reviewed on 4 May 2026
Diamond Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 2,500 |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 27ºC |
Top Sights | Heidecke Lake State Fish and Wildlife Area, Gebhard Woods State Park and William G. Stratton State Park |
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Diamond IL
Red Roof Inn Chicago - Joliet
1750 Mcdonough St Joliet IL
Fully refundableReserve now, pay when you stay
The price is £45 per night from 31 May to 1 Jun
£45
31 May - 1 Jun
includes taxes & fees
6.8/10 (1,013 reviews)
This place is nasty. The bathtub has rust in it and the TV remote does not work.
Reviewed on 5 May 2026
Wingate by Wyndham - Joliet
101 McDonald Avenue Joliet IL
Fully refundableReserve now, pay when you stay
The price is £77 per night from 19 May to 20 May
£77
19 May - 20 May
includes taxes & fees
8.4/10 Very Good! (1,002 reviews)
Always check to see if there’s construction going on in the hotel. They’re updating all the rooms and didn’t let us know and we had to live through all the noise and the loud worker staying at the hotel. Irritating and they were very rude.
Reviewed on 12 May 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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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.
