South Side Holidays from £955
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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 £1,123, price is now £955 per person
£955
per person
1 Jul - 5 Jul
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
8.2/10 Very Good! (2,707 reviews)
The staff at Hotel Felix were kind, thoughtful, and genuinely helpful throughout my stay. The location is also a strong point — walking distance to a lot of great Chicago spots, which made getting around easy.
My experience was somewhat diminished by the mandatory Urban Fee added at check-in. I understand many hotels are moving in this direction, but travelers should be aware of the additional required cost when budgeting for their stay. Outside of that, the team and location were the highlights for me.
Reviewed on 12 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 18 hours ago
Return flight included
London (LON) to Chicago (ORD)
8.4/10 Very Good! (2,293 reviews)
Quiet, clean space. Great bedding. Location to airport terminals a short walk.
Reviewed on 14 May 2026
Swissotel - Chicago
Downtown Chicago
Price was £1,238, price is now £991 per person
£991
per person
1 Jul - 5 Jul
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
It’s my favorite hotel always clean smell good and river walk across the street and all the staff always very helpful
Reviewed on 15 May 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was £1,242, price is now £1,041 per person
£1,041
per person
1 Jul - 5 Jul
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (3,692 reviews)
Great location.
Very friendly and helpful staff.
Reviewed on 13 May 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was £1,164, price is now £981 per person
£981
per person
1 Jul - 5 Jul
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
8.8/10 Excellent! (2,148 reviews)
Staff was very good, attentive. The property itself is in a great location, but the room showed some wear and tear - exposed drywall screws holding on bathroom door trim with some paint slapped on it, smelly sink, water damage and peeling paint on inside window sill, visually boring interior that looks like it's from the 1990's
Reviewed on 12 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 £70 per night from 26 May to 27 May
£70
26 May - 27 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 £94 per night from 17 May to 18 May
£94
17 May - 18 May
includes taxes & fees
9.4/10 Exceptional! (847 reviews)
They definitely took a rundown, stripped motel and made it into this really sweet and quaint beautiful place where you can just come back and rest after a day running around. They have a fire pit and a gazebo with a table of pool and a Swing, which I thought was very nice. The staff was super helpful ...
Reviewed on 13 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.