Chicago is a big diversified city and if you are not familiar with the city, then I recommend an itinerary for visiting. My first suggested itinerary for Chicago is geared towards the sports fan. My second recommended itinerary for Chicago visitors is for shopping . My third suggested Chicago Itinerary is for cultural visitors in this great city. All of these itineraries are for a two day stay.
Two day sports itinerary for Chicago
Day one
No sports fan can visit Chicago without a trip to Wrigley Field, and hopefully you will be visiting during baseball season and take in a game. Remember if you catch a homerun ball by the visiting team, it is tradition to throw it back on the field. If the timing is wrong to take in the game, there are 90 minute tours of the ballpark.
Keeping with the Baseball theme you would then go check out the White Sox and take in a game at U.S. Cellular Field. The old Comiskey Park was destroyed in 1991.
After visiting the ball parks go to the ESPN Zone and unwind at this great sports bar. Enjoy a meal and a drink or two while enjoying the sporting events on television.
Day Two
Go and see the United Center, home of the Chicago Bulls and Blackhawks. Even if not during basketball or hockey season there are other events here you can attend. Check out their site for details.
Ok no Chicago sports itinerary would be complete without a visit to Soldier Field home of the Chicago Bears. After all Bears is what first comes to mind to sports fan when thinking of the Windy City.
Then have dinner at Mike Ditka’s Restaurant where you can have private dining if you choose. Great food and atmosphere and who knows you may even see Mike Ditka there.
Two Day Shopping Itinerary for Chicago
Day One
My first stop would be at the 900 North Michigan Avenue Shops. Check their site for a list of shops which is too large to list here. But just a few are Bloomingdales, Ethel’s Chocolates, Four Seasons Spa, Gucci, Picture Us, and Walden Books. They also have fine dining and hotel packages. There are 6 floors of shops to choose from here.
While on Michigan Avenue look for all the other shopping opportunities in the area, it is known as the Magnificent Mile. The Water Tower, Pucci and Keneth Cole are in the area. Check this site for more information on shops in the area.
The vast majority of your day should be finished after the first excursion but I would head over to Macy’s for my 2nd outing. They also offer fine dining and hotel packages not to mention the experience of shopping at a historical landmark.
Day Two
If you are into boutiques I would consider a guided tour of Chicago boutiques with this company.
Looking for Jewelry in Chicago? I recommend Wedding Bands and Co located at Madison and Wabash Avenue. They have a wide selection of jewelry and do custom work as well.
I also would go check out the Gold Coast with such stores Underdogg, Sur La Table, Sabron and many more. Check out this site for more details.
To round out the day I would visit the Woodfield Mall on Woodfield Road. They offer close to three hundred shops and restaurants in this Chicago Mall.
Chicago Cultural Visitors Itinerary
Day One
My first stop would be the Field Museum and you can get a discount from their website here. Their exhibits include Mythic Creatures, The Aztec World, and the Ancient Americas plus much more.
Then I would head over to my personal favorite the Chicago History Museum this is an amazing place. Check their website for current exhibits and goings on.
That night I would try to attend an event at the Chicago Symphony Orchestra. They offer over 150 events a year so there is a good chance you can attend one during your visit.
Day Two
Your first stop of the day should be the Arts Institute of Chicago, they offer two libraries as well as art exhibits in the Windy City.
Next go to the Museum of Contemporary Art, at 220 East Chicago Avenue. Check their website for current exhibitions or events.
My favorite for day two would be the Shedd Aquarium a must see if you have children. Their site says they have over 32,000 animals on display. They even have sea cucumbers but I think they frown on an impromptu sandwich!
