You should plan before you start your trip to Chicago, there are many travel agencies help for planning your tours and trips, you must sign in the website and be a member of that the website to get more additional mails.

Take a look on the example planning website:

http://www.explorechicago.org/city/en/trip_planner/usingtripplanner.html

You can also compare the fares of the travel agencies by getting quotations regarding the trip and all the transports, and then you can enter to bookings, check the following link for making a plan:

http://www.orbitz.com/App/DisplayCarSearch?OSC=LX1Q9BYuSL!1373149128!183215146!7001!-1&z=9429&r=b

There are many cruise travel providers in Chicago, check the link for a simple travel agency:

http://local.yodle.com/profile/cruise-holidays-chicagos-cruise-travel-agency-chicago-il/5187413?cid=arb_ssp_cs_10_19&yluid=test

There are some guest houses in Chicago, IL which offers rental facility. Some provides the guest houses on weekly basis, some on daily and some on monthly basis. One has to choose the guest house accordingly.

Some of guest houses which provide rental facility are listed below:

1. Old Town Chicago Guest House- This guest house is located near North Park Avenue in Chicago, IL. The charges for 4 bedroom-4 bathrooms for 4 to 11 people are $4550 to $7000 per week.

2. Chicago Guest House- This guest house also provides rooms on rent. The charges are $396 to $495 per day.

http://www.vacationrentalpeople.com/rental-property.aspx/World/USA/Illinois/Chicago/Guest-House-13100

http://www.vacationrentalpeople.com/rental-property.aspx/World/USA/Illinois/Chicago/Guest-House-9758