Good airlines for a faming travel

The  Piper Arrow

   is suitable for small family sizes.

Large family sizes can look out for the Dakota. More spacious and powerful than the piper arrow. You would also get the chance to interact with other tourists on the airline.

The Beechcraft Bonanza

. Most of those aircraft should get you pretty close to the East coast non-stop from Chicago, it might be cutting it pretty close on fuel, though. Cessna 177, 182, 206, or 210

 The Cessna 182

is the model most people agree to be one of the best. It's a proven workhorse, been around for decades, has at least a 600-650nm range, is easy to work on and parts are plentiful.
Its impressive interior designs also makes it suitable for a tour around the city..

It can hold about 4 passengers in a flight making it the best choice for small families.



Versions of the AB-95 are also good alternatives : includes the AB-95 Standard, the AB-95 De Lujo with a 75kW (100hp) Continental O-200A engine, the AB-95A Fumigador ag aircraft with the O-200A engine and fitted for crop dusting or spraying, the AB-115BS air ambulance fitted with a stretcher, the more powerful AB-95B, and the AB-95-115 with a more streamlined engine cowling housing a 85kW (115hp) O-235 engine, and main wheel fairings.


From the AB-95-115 Aero Boero

        

 developed the AB-115BS with increased wing span, greater fin sweepback and longer range, and the AB-115 Trainer. Brazil ordered 450 Trainers in the late 1980s for its aero clubs. 

                           

The AB-180 first flew in the late 1960s and was offered in three and four seat versions with differing wingspans and a more powerful powerplant than those featured on the earlier AB-95 and AB-115. Developments included the AB-180RV with greater range, reprofiled fuselage and sweptback fin; the glider tug AB-180RVR; the high altitude AB-180 Condor with optional engine turbocharger; AB-180AG agricultural aircraft and the two seat AB-180PSA preselection aircraft for student pilot flight grading. An experimental biplane AB-180SP was also developed.           

The  Piper Arrow, Dakota, or anything larger; ; or Beechcraft Bonanza. Most of those aircraft should get you pretty close to the East coast non-stop from Chicago, it might be cutting it pretty close on fuel, though. I would personally suggest a turbo pressurized Cessna 210. It'll be able to get you to the east coast and be able to handle the high altitudes out west. You'll need to have a high performance/complex to fly it and instrument rating to take full advantage of it though. Enjoy your travels!

With this in mind, I agree fully with the answer Cessna 182. During this financial crunch that is still up to debate whether we will get out of or not, the C-182 prices have now been in the range of what I would call normal. That is, you can get a mid to late 80's 182 with a fresh annual and low hour engine for the low to mid 100's. This will get you a plane that can haul three adults with all the luggage you can fit into the other open seat and luggage area or four adults with nominal luggage each. All of this with full tanks and the range your looking for.

These planes are also good options

Piper PA-6 Sky Sedan

 Can be piloted by 1 with a capacity of 4 powered by a one Franklin, 140 hp (100 kW) with a maximum speed of 140 mph (230 km/h)

Piper Cherokee Six

 Piloted by one (capacity of five or six) with a gross weight of 3400 Ib. A maximum speed of 174 mph (280 km/h) though cruise speed is 168 mph. The range is 840 miles. It is a single engine plane.

Piper PA-28 Cherokee

 Capacity of three passengers with a NACA 652-415 Airfoil and a take-off maximum weight of 2150 Ibs. Cruise speed is 108 knots (124 mph, 201 km/h), stall speed is 47 knots. Range is 465 nautical miles (867 km) - single engine.

Cessna 172

 Single engine, four seat aircraft with a max take off weight of 2,450 Ib. Maximum speed of 123 knots, cruise speed at 122 knots (140 mph, 226 km/h), range of 610 nautical miles (790 miles or 1272 km) at 55% power at 12000 feet.

Beechcraft Musketeer

 Four seat aircraft, 2400 Ib takeoff weight, 650 mile range, cruise speed of 146 mph (235 km/h)