You can find many parks in Chicago, IL where you can take your pets along with you. Some of the parks even have special facilities which will make your trip a real joy. If you are going along with your friends or family members then you can take the help of pet sitters who will take care of your pets.

Below mentioned are some of the popular pet parks:

- Grant bark park - this is located at 900 S Columbus Dr

- Pup town park - you can get to this park at 4921 N Marine Dr

- Winnemac park - it is at 5100 N Damen Avenue

- Hamlin Dog Park etc.

http://www.yelp.com/search?find_desc=dog+friendly+parks&find_loc=Chicago%2C+IL

Most of the good hotels are equipped with swimming pools in Chicago, IL. Some of the hotels are:

- The Palmer House Hilton

- The Peninsula Chicago

- Lakeshore - W Chicago

- Intercontinental Chicago

- Four Seasons Hotel

- Park Hyatt Hotel

The Palmer House is a gorgeous hotel in Chicago, IL with 1,639 rooms. It has an indoor pool and a fitness center. The other hotels also have great swimming pools and spas for their guests where you can relax in the pool and have a splendid time.

http://www.travelmuse.com/hotels-with-swimming_pool-chicago-illinois-031-il-us

http://www.tripadvisor.com/Hotels-g35805-zfa3-Chicago_Illinois-Hotels.html