South Side Fishing Holidays
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Top flight + Fishing hotel deals in South Side
Price found within the past 48 hours. Click for updated prices.
Bluegreen Vacations Hotel Blake, Ascend Resort Collection
Downtown Chicago
per person
12 Sept - 16 Sept
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (1,004 reviews)
All staff were very friendly and helpful. Hotel was in convenient location for walking.
Reviewed on 27 Jul 2025
Pendry Chicago
Downtown Chicago
per person
5 Oct - 8 Oct
found 22 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,031 reviews)
The stay so far has been great, but we attempted to order in room dining which, according to the menu, is available until 5AM, but were advised by the front desk staff that we would not be able to order food for at least 40 minutes while the kitchen was “cleaned”. No other solutions were provided and we were very disappointed in this interaction.
Reviewed on 30 Jul 2025
5* Fishing holidays in South Side
Price found within the past 48 hours. Click for updated prices.
The Peninsula Chicago
Downtown Chicago
per person
8 Sept - 12 Sept
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Just a fantastic check-in, very classy hotel and went overboard decorating for my 19-year-old’s birthday and giving Little goodies!
Reviewed on 26 Jul 2025
3 Night Fishing holidays in South Side
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
per person
19 Sept - 22 Sept
found 21 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,253 reviews)
I loved how smooth the check in process was and all the amenities. Great rooms.
Reviewed on 1 Aug 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
19 Sept - 22 Sept
found 21 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,659 reviews)
Great, comfortable beds, spacious rooms. The bathroom was very clean and spaciousZ loved it
Reviewed on 3 Aug 2025
4 Night Fishing holidays in South Side
Price found within the past 48 hours. Click for updated prices.
Level Chicago - River North
Downtown Chicago
Save 100% on your flight
per person
4 Oct - 8 Oct
found 21 hours ago
Return flight included
Toronto (YYZ) to Chicago (ORD)
9/10 Wonderful! (652 reviews)
Quick and easy check in. Parking in their private garage was breeze. Plenty of space, mostly empty, and our vehicle could stay in the garage until 2:00 PM the next day. Beautiful 1 BR condo. Full kitchen, beautiful views of the city on the balcony and from the living room, and very clean space overall. Need your key card for just about everything (pool, lounge, some of the outdoor bathrooms, elevators, etc.).
Reviewed on 27 Jul 2025
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Save 100% on your flight
per person
5 Oct - 9 Oct
found 21 hours ago
Return flight included
Toronto (YYZ) to Chicago (ORD)
9/10 Wonderful! (1,000 reviews)
Beautiful historic old building, with significant attention paid to historical preservation in conversion to hotel. Quiet, relaxing atmosphere in lobby and contiguous rooms.
The advertised “view of Millennium Park” was exaggerated, actually only possible if one kneels on the sofa and cranes your neck. Shower is problematic as the glass enclosure leaks, creating a huge puddle extending across the entire room to the toilet. It took 5 large bath towers to sop it up. Otherwise we had a pleasant stay.
Reviewed on 28 Jul 2025
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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.