South Side Holidays from £1,397
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Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was £1,849, price is now £1,397 per person
£1,397
per person
31 Jul - 5 Aug
found 21 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
8.2/10 Very Good! (2,707 reviews)
It was very close to restuarants, easy to find and very accessible. All staff were really helpful.
Reviewed on 16 May 2026
Hilton Chicago O'Hare Airport
O'Hare
Price was £1,902, price is now £1,508 per person
£1,508
per person
5 Aug - 12 Aug
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
8.4/10 Very Good! (2,293 reviews)
Clean room, comfortable beds and pillows, great coffee shop in lobby.
Reviewed on 16 May 2026
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
Downtown Chicago
Price was £2,548, price is now £2,056 per person
£2,056
per person
31 Jul - 5 Aug
found 21 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (1,006 reviews)
No coffee machines in the room but free coffee in the lobby. Great location. The bar is a scene and the rooftop patio is a beautiful space. Great sound insulation and comfy beds.
Reviewed on 13 May 2026
Swissotel - Chicago
Downtown Chicago
Price was £1,866, price is now £1,513 per person
£1,513
per person
3 Aug - 7 Aug
found 5 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
It was very pleasant and safe. I liked that you needed a room key to use the elevator which made us feel safe. The hotel is located very central and walking distance to everything. The staff was very friendly.
Reviewed on 16 May 2026
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was £2,012, price is now £1,662 per person
£1,662
per person
31 Jul - 5 Aug
found 21 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,059 reviews)
Easy access to many points of interests and shopping
Reviewed on 16 May 2026
Where to stay in South Side
Find the best South Side areas and neighborhoods for the activities you enjoy most. Learn more about South Side
North Side
1 out of top 10 points of interest in this area
While visiting North Side, you might make a stop by sights like Michigan Maritime Museum and North Beach.
Top hotels in South Side
Overlook South Haven Harbor steps from South Beach and Downtown
South Haven MI
10/10 Exceptional! (189 reviews)
We love South Haven in October and this trip did not disappoint! The location and charm of Crimson Sun was just what we were looking for.
Reviewed on 21 Oct 2025
Baymont by Wyndham South Haven
1555 Phoenix Rd South Haven MI
Fully refundableReserve now, pay when you stay
The price is £83 per night from 17 May to 18 May
£83
17 May - 18 May
includes taxes & fees
7.8/10 Good! (1,001 reviews)
Convenient location with very reasonable pricing.
Reviewed on 8 May 2026
Starlite Resort
3353 Blue Star Highway Saugatuck MI
Fully refundableReserve now, pay when you stay
The price is £102 per night from 2 Jun to 3 Jun
£102
2 Jun - 3 Jun
includes taxes & fees
9.4/10 Exceptional! (848 reviews)
Quaint motel very well upkept. Has a classic Americana / Route 66 feel but it's near Lake Michigan. Multiple fire pits, grills, play area, and quiet!! Highly recommend.
Reviewed on 16 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.
* 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.