Title: Pet-friendly Vacations in Far Southeast Side 2026 | Expedia.ca

![](https://images.trvl-media.com/place/829/b4cf8e95-0f92-4795-af28-19f97bbf7dad.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Far Southeast Side Pet-friendly Vacations

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## Flight and Pet-friendly hotel deals in Far Southeast Side

Price found within the past 48 hours. Click for updated prices.

![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Riu Plaza Chicago

Downtown Chicago

CA $762

per person

May 8 - May 11

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (3,495 reviews)

Great location. Clean, comfortable, friendly staff.

Reviewed on Mar 30, 2026

![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

CA $1,063

per person

May 8 - May 11

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,401 reviews)

Amazing experience will be back soon

Reviewed on Mar 29, 2026

![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/989904ac_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago Fulton Market

Downtown Chicago

CA $1,178

per person

Jun 20 - Jun 23

found 23 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Chicago (ORD)

9.2/10 Wonderful! (421 reviews)

10/10 makes you feel at home. One of the best hotels I’ve ever stayed in.

Reviewed on Mar 23, 2026

![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8c061e2a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago – Old Town

Downtown Chicago

CA $1,534

per person

Jun 7 - Jun 10

found 3 hours ago

Roundtrip flight included

Calgary (YYC) to Chicago (ORD)

9/10 Wonderful! (441 reviews)

The rooms are extremely clean and have everything you need. The staff is so accommodating and friendly. The view is amazing

Reviewed on Mar 27, 2026

![Staypineapple, An Iconic Hotel, The Loop](https://images.trvl-media.com/lodging/1000000/290000/284800/284792/bbf9e380_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Staypineapple, An Iconic Hotel, The Loop

Downtown Chicago

CA $1,019

per person

Jun 19 - Jun 22

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,021 reviews)

Great property, so many cute details in this historic hotel. The staff was friendly, the property was pristine, and it’s close to so many things to visit and do in Chicago. A close walk to Millennium Park, and many shops.

Reviewed on Mar 27, 2026

Don't see what you're looking for?

See all available trips from Columbus to Far Southeast Side

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-04-30/2026-05-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 5\* Pet-friendly holidays in Far Southeast Side

Price found within the past 48 hours. Click for updated prices.

![The Ritz-Carlton, Chicago](https://images.trvl-media.com/lodging/1000000/20000/14500/14447/29a217ee_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Ritz-Carlton, Chicago

Downtown Chicago

CA $1,418

per person

May 8 - May 11

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,001 reviews)

Enjoyed a very comfortable stay.

Reviewed on Mar 30, 2026

![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c8149674_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Park Hyatt Chicago

Downtown Chicago

CA $3,796

per person

Jun 3 - Jun 8

found 24 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.6/10 Exceptional! (1,004 reviews)

Room clean , large comfoy

Reviewed on Mar 15, 2026

![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/4465cc02_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,638

per person

Jun 19 - Jun 22

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,852 reviews)

Thank you for your exceptional hospitality

Reviewed on Mar 29, 2026

Don't see what you're looking for?

See all available trips from Columbus to Far Southeast Side

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-04-30/2026-05-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 3 Night Pet-friendly holidays in Far Southeast Side

Price found within the past 48 hours. Click for updated prices.

![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Riu Plaza Chicago

Downtown Chicago

CA $762

per person

May 8 - May 11

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (3,495 reviews)

Great location. Clean, comfortable, friendly staff.

Reviewed on Mar 30, 2026

![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

CA $1,177

per person

Jun 19 - Jun 22

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Chicago (ORD)

9.4/10 Exceptional! (2,401 reviews)

Amazing experience will be back soon

Reviewed on Mar 29, 2026

![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8c061e2a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago – Old Town

Downtown Chicago

CA $978

per person

May 8 - May 11

found 4 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (441 reviews)

The rooms are extremely clean and have everything you need. The staff is so accommodating and friendly. The view is amazing

Reviewed on Mar 27, 2026

Don't see what you're looking for?

See all available trips from Columbus to Far Southeast Side

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-04-30/2026-05-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 4 Night Pet-friendly holidays in Far Southeast Side

Price found within the past 48 hours. Click for updated prices.

![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8c061e2a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago – Old Town

Downtown Chicago

CA $1,346

per person

Apr 30 - May 4

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Chicago (ORD)

9/10 Wonderful! (441 reviews)

The rooms are extremely clean and have everything you need. The staff is so accommodating and friendly. The view is amazing

Reviewed on Mar 27, 2026

![Viceroy Chicago](https://images.trvl-media.com/lodging/19000000/18620000/18614200/18614145/69dc07eb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Viceroy Chicago

Downtown Chicago

CA $1,546

per person

May 26 - May 30

found 15 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,187 reviews)

Very nice place on the Gold Coast!

Reviewed on Mar 23, 2026

![LondonHouse Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/7aab5ae1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

CA $1,375

per person

May 6 - May 10

found 7 hours ago

Roundtrip flight included

Toronto (YTZ) to Chicago (ORD)

9.4/10 Exceptional! (3,646 reviews)

Super clean, super friendly staff.

Reviewed on Mar 29, 2026

Don't see what you're looking for?

See all available trips from Columbus to Far Southeast Side

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-04-30/2026-05-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## Pet-friendly Hotels in Far Southeast Side

![Admiral Motel By Oyo Chicago I-94](https://images.trvl-media.com/lodging/113000000/112490000/112484100/112484089/cdb6bc21_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Admiral Motel By Oyo Chicago I-94

9118 S Cottage Grove Ave Chicago IL

- 19 min walk from Abbott Park

Stay at this hotel in Chicago. Enjoy free parking, room service, and a 24-hour front desk. Popular attractions Griffin Museum of Science and Industry and Jackson ...

[](https://expedia.ca/Chicago-Hotels-Admiral-Motel-By-Oyo-Chicago-I-94.h112484089.Hotel-Information)

![4/20 Friendly 12PM Check Out 1 Bedroom Basement](https://images.trvl-media.com/lodging/124000000/123230000/123225500/123225487/0a35506e_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

4/20 Friendly 12PM Check Out 1 Bedroom Basement

 Chicago IL

- 5 min drive from Abbott Park

Stay at this vacation home in Chicago. Popular attractions Griffin Museum of Science and Industry and Jackson Park are located nearby.

10/10 Exceptional! (1 review)

Perfect for parties love every thing about it

Reviewed on Mar 14, 2026

[](https://expedia.ca/Chicago-Hotels-420-Friendly-12PM-Check-Out-1-Bedroom-Basement.h123225487.Hotel-Information)

![ Charming 5 bedrooms 2 bath near Downtown Loop and Mc cormick Place, Museum ](https://images.trvl-media.com/lodging/100000000/99700000/99692300/99692300/dfe91bbb_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

 Charming 5 bedrooms 2 bath near Downtown Loop and Mc cormick Place, Museum 

 Chicago IL

- 6 min drive from Abbott Park

Stay at this vacation home in Chicago. Enjoy a garden, laundry facilities, and patios. Popular attractions Griffin Museum of Science and Industry and Jackson ...

[](https://expedia.ca/Chicago-Hotels-Charming-5-Bedrooms-2-Bath-Near-Downtown-Loop-And-Mc-Cormick-Place.h99692300.Hotel-Information)

[See all 4,678 properties in Far Southeast Side](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&regionId=553248635976475411)

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.

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## More Vacations Ideas

[Flights to Far Southeast Side

](https://expedia.ca/Cheap-Flights-To-Far-Southeast-Side.d553248635976475411.Travel-Guide-Flights)[

Far Southeast Side Hotels

](https://expedia.ca/Far-Southeast-Side-Hotels.d553248635976475411.Travel-Guide-Hotels)[

Far Southeast Side Vacation Rentals

](https://expedia.ca/Far-Southeast-Side-Vacation-Rentals.d553248635976475411.Travel-Guide-VacationRentals)[

Far Southeast Side Car Rentals

](https://expedia.ca/Car-Rentals-In-Far-Southeast-Side.d553248635976475411.Car-Rental-Guide)[

Far Southeast Side Vacations

](https://expedia.ca/Far-Southeast-Side.d553248635976475411.Destination-Travel-Guides)

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

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