1.Wrigleyville – Boystown

Fresh off an historic Cubs victory, Wrigleyville is definitely among the top spots to visit during the last few weeks of warm weather. The north side is abundant with quaint eateries and bars with street-facing patio decks from which to view the gentle flow of activity. Chicago visitors looking for nightlife in an area not as imposing (or pricey) as the Loop might consider taking the red line to Belmont or Addison where the city takes on a different atmosphere. The streets are narrower, the area more residential, and the feeling is intimate compared to the city’s vertical core.

2.Little Italy – Taylor Street

Today’s Little Italy is only a fraction of what was once a large Italian community composed of natives and immigrants alike, located in the west loop backed up to Halstead. Despite the disappearance of many of the original communities in the area, a short walk down Taylor Street will send you down a strip of eclectic cuisine and pleasant parks to experience Autumn in the city. Italian, Greek, and Indian are some of the neighborhood’s featured food choices. The area's proximity to the University of Illinois provides a relaxed yet active ambiance appreciated by students, tourists and locals alike.

3.Chinatown

Take the red line a few stops south of downtown and reach Chinatown. Terrific restaurants, unique shopping, and bubble tea – Chinatown is the place. The markets in Chinatown offer an experience unlike any other in the city. Looking for durian or lychee? You will certainly find both here. If you are new to bubble tea, don’t remain a stranger, because it’s fantastic. Granted you can find it anywhere now, but know you will come across it here. In addition, the Chicago Public Library System recently opened its newest location in Chinatown. With its glossy finish and specific style of architecture, this original utility is worth a visit.

4.West Loop

Chicago’s West Loop is a quickly developing community with a young population and the independent cafes to prove it. The former industrial quarter known for its textile plants in the late nineteenth and early twentieth century has in recent years experienced a renaissance. The trendy area is home to neighborhoods including Greektown on Halstead and to the north Fulton Market on Randolph. The West Loop is unique in that is diverse in its amenities. Farther up Halstead boasts bars and an active nightlife with views of the skyline. Keep west, and the United Center where the Bulls and Blackhawks play marks the edge of the loop. The West Loop is a big area, with plenty to take advantage of.

5.Grant Park – Lake Front

OK, Grant Park is beautiful any time of year, nothing challenges the fall colors though. Stroll down Michigan, pay the Art Institute a visit, have a coffee. My personal favorite, head east down Roosevelt past the Field Museum and Shedd. From here you will simply not find a better angle from which to view the city. Run to the Adler just before dawn, the Sun rises over the lake and the water is crystal – perfect.

6.River Walk

If you are not a fan of River North because it’s too congested or too mainstream, spend at least a few hours walking along the extended river walk recently installed and opened in October. The city of Chicago has done a terrific job renovating the spaces along the river. Featuring restaurants, cafes, parks, and seating the long awaited effort is an instant classic.