This is a listing of a few possible day trips you can make from Chicago.

North:

The Chicago Cubs and Andersonville boutique shopping.  If not everyone is interested in baseball, it is a good location to split up the group.  There is a nearby northside neighborhood called Andersonville that is great for dining and boutique shopping.  With a little planning, you can take in a Pilates, Yoga or Cooking classes and socialize a bit... it is not well-known by tourists and is full of hidden gems.  It is easily accessible by cab along lake shore drive, the CTA redline, the CTA 22 Bus from Wrigely Field.  Dining - don't miss:  Hop Leaf (Belgian), M Henry (brunch), Lady Gregory (Irish), Ann Sathers (Swedish) and Acre/Ombra (American/Italian tapas).   

Chicago Botanic Garden  1000 Lake Cook Road, Glencoe,  IL 60022  ( 847-835-5440 ) . It is 20 miles North of Chicago.  Huge botanic garden with a lot to see. 

The town of Gurnee, about 45 miles north of the loop, is well known for two attractions - the huge Gurnee Mills shopping mall and Six Flags Great America with its awesome collection of coasters and new water park.  If you are visitng the area on a summer weekend, you can also enjoy the Bristol Renaissance Faire on the Illinois / Wisconsin state line.

Milwaukee  is about 85 miles north of Chicago and has its own set of attractions as a large city.

 

West:

For the kids, the Chicago Zoological Society in Brookfield, a short distance west of Chicago, is one of the country's largest and is particularly known for its enclosed habitats.  It is also one of the relatively few zoos to have okapis, an animal once described by the Chicago Tribune as looking like it had been designed by a bunch of Chicago aldermen.

A nice day trip for shppers to to take I-88 west to Aurora and then head north to the Geneva (not to be confused with Lake Geneva, Wisconsin)  / St. Charles area.  Both villages are very lovely and quaint with a number of upscale shopping and dining venues.  If they prove too pricey, head instead to the Chicago Premium Outlets in Auruora to visit one of the areas largest outlet malls.

 

Northwest:

The Illinois Railway Museum off of I-90 in Union is a wonderful collection with a lot of rolling stock.  Many special events and train rides on summer weekends.  Both the big and little kids will love this one.    Further west on I-90, about 90 miles from the Loop, is the city of Rockford which boast a number of sightseeing attractions.

In a slightly more northerly direction, you can stop at the antique shop filled town of Richmond before heading to theLake Geneva area in southern Wisconsin, a popular getaway for Chicagoans for 150 years.

 

Southwest:

Starved Rock State Park  is a popular hiking and picnickking location.  It is 100 miles west southwest of the loop.

 

The Middle East Conflicts Wall Memorial is located on the south side of the village of Marsailles, just 77 miles southwest of Chicago's city center off on Interstate 80 at exit 97. Friends and family members of fallen veterans from recent military conflicts in the Middle East may use the information kiosks located at the memorial to locate names of loved ones engraved into the granite.  Etching papers are also available to transpose engraved names to take with them.  There is a museum located in the building on the west side of the parking lot where one may view the mementos, articles, and stories left behind by visitors of the heroes whose names are found on the wall.  Each year on the Saturday before Father's Day, the Illinois Motorcycle Freedom Run conducts a tribute ride from Grundy Fairgounds to the memorial. 

 

 East:

The southern and western shores of Lake Michigan are popular summer beach spots for Chicagoans.  Check out the Indiana Dunes National Lakeshore.

 On the south lakeshore is the 31st Street Harbor - which is a beautiful new harbor and the winner of the Fabien Cousteau Blue Award in 2012. It also is the host of the very fun Chicago Water Sport Rentals, which rents various water equipemnt from state-of-the-art kayaks to paddleboards to incredible jet skis. It has enough fun for everyone and is a great way to spend a summer afternoon!

Further afield, in Michigan, is the popular  New Buffalo Area.