Southern Wisconsin Cheap Holidays
Book a Cheap Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to £335 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 + Cheap hotel deals in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North
Downtown Chicago
Save 100% on your flight
Price was £1,455, price is now £894 per person
£894
per person
3 Oct - 10 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (2,028 reviews)
Close to walk most places. Lots of restaurants in the surrounding area. Staff very nice. Rooms clean and spacious.
Reviewed on 22 Aug 2025
Level Chicago - River North
Downtown Chicago
Save 100% on your flight
Price was £1,643, price is now £1,044 per person
£1,044
per person
3 Oct - 10 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (666 reviews)
Hotel is located very centric. Nice view very quiet
Reviewed on 22 Aug 2025
Arlo Chicago
Downtown Chicago
Save 100% on your flight
Price was £1,519, price is now £1,034 per person
£1,034
per person
3 Oct - 10 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,825 reviews)
Staying here was nothing short of amazing thanks to this staff. They were very friendly, courteous and nice. Everyone was attentive and you can tell. They really loved working there and delivering service.
Reviewed on 20 Aug 2025
Virgin Hotels Chicago
Downtown Chicago
Save 100% on your flight
Price was £1,636, price is now £1,118 per person
£1,118
per person
3 Oct - 10 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,336 reviews)
No hot water in the shower for the entirety of our 3 night stay, it was barely warm. Complained multiple times, other guests were also facing the same problem. The responses ranged from "engineers are working on it" to "leave the water running for longer" to finally "that is the hottest water you're going to get". That was unbelievable given that the sink had hotter water than the shower. Upon my insistence, they offered to move us to a different room the next day after 3pm - that meant we would have had to take cold showers for 2 days. In the end we just didn't take up the moving-rooms hassle in the middle of our trip.
Reviewed on 18 Aug 2025
The Langham, Chicago
Downtown Chicago
Save 100% on your flight
Price was £2,345, price is now £1,604 per person
£1,604
per person
25 Oct - 1 Nov
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on 12 Aug 2025
Don't see what you're looking for?
See all available trips from London to Southern Wisconsin
View all trips5* Cheap holidays in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Park Hyatt Chicago
Downtown Chicago
Price was £2,947, price is now £1,375 per person
£1,375
per person
11 Nov - 14 Nov
found 19 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!
Reviewed on 10 Aug 2025
The Langham, Chicago
Downtown Chicago
Save 100% on your flight
Price was £2,345, price is now £1,604 per person
£1,604
per person
25 Oct - 1 Nov
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on 12 Aug 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was £2,481, price is now £1,795 per person
£1,795
per person
9 Oct - 13 Oct
found 13 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.
Reviewed on 19 Aug 2025
Don't see what you're looking for?
See all available trips from London to Southern Wisconsin
View all trips3 Night Cheap holidays in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North
Downtown Chicago
Save 100% on your flight
Price was £710, price is now £475 per person
£475
per person
14 Oct - 17 Oct
found 1 day ago
Return flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (2,028 reviews)
Close to walk most places. Lots of restaurants in the surrounding area. Staff very nice. Rooms clean and spacious.
Reviewed on 22 Aug 2025
Level Chicago - River North
Downtown Chicago
Save 100% on your flight
Price was £780, price is now £547 per person
£547
per person
14 Oct - 17 Oct
found 1 day ago
Return flight included
Toronto (YYZ) to Chicago (ORD)
9/10 Wonderful! (666 reviews)
Hotel is located very centric. Nice view very quiet
Reviewed on 22 Aug 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was £1,391, price is now £1,011 per person
£1,011
per person
18 Nov - 21 Nov
found 1 day ago
Return flight included
London (LCY) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.
Reviewed on 19 Aug 2025
Don't see what you're looking for?
See all available trips from Toronto to Southern Wisconsin
View all trips4 Night Cheap holidays in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North
Downtown Chicago
Save 100% on your flight
Price was £681, price is now £373 per person
£373
per person
3 Oct - 7 Oct
found 1 day ago
Return flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (2,028 reviews)
Close to walk most places. Lots of restaurants in the surrounding area. Staff very nice. Rooms clean and spacious.
Reviewed on 22 Aug 2025
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was £1,509, price is now £873 per person
£873
per person
14 Oct - 18 Oct
found 1 day ago
Return flight included
Toronto (YYZ) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!
Reviewed on 10 Aug 2025
Level Chicago - River North
Downtown Chicago
Save 100% on your flight
Price was £810, price is now £480 per person
£480
per person
3 Oct - 7 Oct
found 1 day ago
Return flight included
Toronto (YYZ) to Chicago (ORD)
9/10 Wonderful! (666 reviews)
Hotel is located very centric. Nice view very quiet
Reviewed on 22 Aug 2025
Don't see what you're looking for?
See all available trips from Toronto to Southern Wisconsin
View all tripsMore 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.