
West Side Fishing Holidays
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Top flight + Fishing hotel deals in West Side
Price found within the past 48 hours. Click for updated prices.


Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
4 Aug - 11 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,623 reviews)
Amazing hotel with large rooms right off Michigan avenue. Staff is amazing, they are always friendly and helpful.
Reviewed on 27 Jun 2025


Arlo Chicago
Downtown Chicago
per person
4 Aug - 11 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,769 reviews)
Comfortable, stylish, friendly hotel in a fabulous location near Millennium Park, Art Institute, and Riverwalk. Friendly staff throughout but the cherry on top was Antoine who checked our bags and arranged out transportation to the airport when we checked out
Reviewed on 29 Jun 2025

5* Fishing holidays in West Side
Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
4 Aug - 11 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,623 reviews)
Amazing hotel with large rooms right off Michigan avenue. Staff is amazing, they are always friendly and helpful.
Reviewed on 27 Jun 2025


3 Night Fishing holidays in West Side
Price found within the past 48 hours. Click for updated prices.

Swissotel - Chicago
Downtown Chicago
per person
4 Sept - 7 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
8.8/10 Excellent! (2,274 reviews)
The staff were marvelously friendly and helpful, and the room had spectacular views of the Chicago River, Lake Michigan, Navy Pier, the Wrigley Building and more. Nice gym on 43rd floor, too. Wonderful sunrises and sunsets. Nicely located not too far from Michigan Avenue and easy access to the Riverwalk. Awesome stay.
Reviewed on 5 Jul 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
per person
4 Sept - 7 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,623 reviews)
Amazing hotel with large rooms right off Michigan avenue. Staff is amazing, they are always friendly and helpful.
Reviewed on 27 Jun 2025

Level Chicago – Old Town
Downtown Chicago
per person
21 Aug - 24 Aug
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (320 reviews)
This was a wonderful location.
It wasn't a type of stay that I am familiar with, in that, there isn't really a lot of people to reach out to ask for assistance. But, all in all, I would definitely stay there again.
Reviewed on 29 Jun 2025
4 Night Fishing holidays in West Side
Price found within the past 48 hours. Click for updated prices.

Hilton Chicago
Downtown Chicago
per person
27 Aug - 31 Aug
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
8.4/10 Very Good! (1,950 reviews)
The property was very nice until we got to the room. The room seemed more dark and dingy. Very expensive for the quality of the room. Staff were extremely nice and the hotel was more central to different parks and modes of transportation.
Reviewed on 2 Jul 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
per person
15 Sept - 19 Sept
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (2,058 reviews)
Overall it was a beautiful experience. I had a corner suite on a high floor, and the views of Lake Michigan were absolutely stunning truly a highlight of my stay. The check-in process was smooth and the staff at the front desk were incredibly warm and welcoming.
However, I did have one unfortunate experience that put a damper on an otherwise perfect stay. About two hours before checkout, while I was still in the room getting ready (having just gotten out of the shower), a room service staff member entered without me hearing her knock likely due to the music I had playing. Not only did this feel like a significant intrusion on my privacy, but she also began throwing away my drinks that were still on the table.
When I confronted her, she apologized and explained that she had been told I had already checked out. While I understand mistakes happen, it was disappointing that she continued clearing items even after seeing I was clearly still in the room. It was a frustrating and awkward situation that left a negative impression at the end of an otherwise lovely visit.
With better communication between departments and a bit more sensitivity to guests’ privacy, this stay would have been perfect. I truly loved everything else about the hotel and hope this feedback helps improve the experience for future guests.
Reviewed on 28 Jun 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
per person
5 Aug - 9 Aug
found 11 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,623 reviews)
Amazing hotel with large rooms right off Michigan avenue. Staff is amazing, they are always friendly and helpful.
Reviewed on 27 Jun 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.