
Great Lakes Pet-friendly Vacations
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Flight and Pet-friendly hotel deals in Great Lakes
Price found within the past 48 hours. Click for updated prices.



The Iron Horse Hotel
Fifth Ward
CA $1,356
per person
Nov 20 - Nov 25
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
9.2/10 Wonderful! (1,353 reviews)
I have stayed at Iron Horse Hotel several times. Celebrated a birthday and an anniversary there. I have recommended it to many people. When I had a very delayed flight into Milwaukee and I needed a place to stay at the last minute, I was very excited to see I could get a room at the Iron Horse. Sadly, it seems to have gone downhill since my last visit. Every interaction with staff in the past was friendly and aimed at making our stay memorable and enjoyable. This time the staff was unfriendly and only the bare minimum of communication. There are no amenities in the room aside from a keurig. There is a musty smell in the rooms and overly scented smell in the lobby area. The fun bar area at a big curtain across it and the restaurant was a ghost town. When I asked for a late checkout because of my very late arrival, the front desk person begrudgingly allowed for me to stay but only for an hour max. It's a small thing but there was no coffee available in the lobby and the water that was out was only available with paper cone shaped cups. That does not reflect a 4 start hotel experience. I really loved all my previous experiences at the Iron Horse. I'm so sad to see that it is no longer up to the same standards.
Reviewed on Oct 15, 2026

Hotel 505 River North
Downtown Chicago
CA $819
per person
Nov 16 - Nov 19
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9.2/10 Wonderful! (2,924 reviews)
The worst staff I’ve come across. The staff at the desk was extremely unprofessional and rude.
I was also supposed to receive a complimentary bottle of wine as stated in my Expedia reservation and after asking for it multiple times, the ladies at the front desk just laughed at me and told me there wasn’t any.
If this is false advertisement, it should not be included as a complimentary service.
Poor experience from poor staff.
Reviewed on Oct 17, 2026

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View all trips3 Night Pet-friendly holidays in Great Lakes
Price found within the past 48 hours. Click for updated prices.

Hotel 505 River North
Downtown Chicago
CA $819
per person
Nov 16 - Nov 19
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9.2/10 Wonderful! (2,924 reviews)
The worst staff I’ve come across. The staff at the desk was extremely unprofessional and rude.
I was also supposed to receive a complimentary bottle of wine as stated in my Expedia reservation and after asking for it multiple times, the ladies at the front desk just laughed at me and told me there wasn’t any.
If this is false advertisement, it should not be included as a complimentary service.
Poor experience from poor staff.
Reviewed on Oct 17, 2026


The Iron Horse Hotel
Fifth Ward
CA $1,074
per person
Nov 27 - Nov 30
found 15 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Milwaukee (MKE)
9.2/10 Wonderful! (1,353 reviews)
I have stayed at Iron Horse Hotel several times. Celebrated a birthday and an anniversary there. I have recommended it to many people. When I had a very delayed flight into Milwaukee and I needed a place to stay at the last minute, I was very excited to see I could get a room at the Iron Horse. Sadly, it seems to have gone downhill since my last visit. Every interaction with staff in the past was friendly and aimed at making our stay memorable and enjoyable. This time the staff was unfriendly and only the bare minimum of communication. There are no amenities in the room aside from a keurig. There is a musty smell in the rooms and overly scented smell in the lobby area. The fun bar area at a big curtain across it and the restaurant was a ghost town. When I asked for a late checkout because of my very late arrival, the front desk person begrudgingly allowed for me to stay but only for an hour max. It's a small thing but there was no coffee available in the lobby and the water that was out was only available with paper cone shaped cups. That does not reflect a 4 start hotel experience. I really loved all my previous experiences at the Iron Horse. I'm so sad to see that it is no longer up to the same standards.
Reviewed on Oct 15, 2026
Don't see what you're looking for?
See all available trips from Columbus to Great Lakes
View all trips4 Night Pet-friendly holidays in Great Lakes
Price found within the past 48 hours. Click for updated prices.



Hotel 505 River North
Downtown Chicago
CA $878
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (2,924 reviews)
The worst staff I’ve come across. The staff at the desk was extremely unprofessional and rude.
I was also supposed to receive a complimentary bottle of wine as stated in my Expedia reservation and after asking for it multiple times, the ladies at the front desk just laughed at me and told me there wasn’t any.
If this is false advertisement, it should not be included as a complimentary service.
Poor experience from poor staff.
Reviewed on Oct 17, 2026
Don't see what you're looking for?
See all available trips from Columbus to Great Lakes
View all tripsPet-friendly Hotels in Great Lakes

Chelsea Hotel, Toronto
22 Elm St Toronto ON
Book a stay at this family-friendly hotel in Toronto. Enjoy free WiFi, 2 indoor pools, and a rooftop terrace. Our guests praise the pool and the restaurant in ...

River Hotel
75 East Wacker Drive Chicago IL
- 16 hours drive from Lake Superior
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...

The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
- 16 hours drive from Lake Superior
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
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.
Things to do

World of Coca-Cola General Admission Ticket
CA $38
per adult
90% of travellers recommend

Atlanta: Center for Puppetry Arts, Worlds of Puppetry Museum
CA $25
per adult
100% of travellers recommend

Atlanta: Atlanta Braves' Truist Park Guided Tour
CA $49
per adult
100% of travellers recommend
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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.







