As told by DIWYY guest writer, Patricia, who grew up in Chicago and continues to make trips back.
Getting There: Chicago has two airports, Chicago O’Hare (ORD), and Chicago Midway (MDW). Upon arrival, you can take the train or a taxi into downtown.
Accomodation Recommendations: I usually stay with friends or family, but if you can afford it, book a reservation with a hotel located downtown. Most of Chicago’s shopping and attractions are located downtown, so it’s best to stay there. You can find great hotel deals on Priceline.com and Hotels.com. Also, if you want other travelers’ reviews on hotels, go to TripAdvisor. The last hotel I made reservations with, the Omni Chicago Hotel, was due to advice/recommendations from these websites. I admit, I had an awesome stay at the Omni.
Patricia’s Recommendations for things to do: From museums to professional sports events to neighborhood festivals to world class dining – there is plenty to do and see in Chicago. This can also make it very difficult to plan a trip itinerary, so I would recommend checking out the many tours the city has to offer.
During my last trip, I brought along two friends who had never been to city. So I researched tours that showcased Chicago’s history, culture, and architecture. The first tour I booked was with Bobby’s Bike Hike. Bobby’s features four different biking tours that range from 4-8 miles in length, so it’s a great way to sightsee and get your exercise. The tour that my friends and I chose was The Obama Bike Tour, which took us all around the Hyde Park neighborhood where President Obama and his family resided. We not only saw the President’s former hangouts, such as his favorite restaurant Dixie Kitchen & Bait Shop and the lecture hall he taught in at the University of Chicago Law School, but we also spotted Muhammad Ali’s childhood home, Frank Lloyd Wright’s Robie House, and the site of the first nuclear reaction.
The next tour we went on was a walking tour of modern skyscrapers. We decided to book this tour with the Chicago Architectural Foundation (CAF) because of the stunning downtown high-rises, as well as the happy hour drink that came at the end of the tour. While the tour was very informative, it was also difficult to hear our docent due to the noise (cars honking, El train passing the tracks, etc.). I did notice that the last group had tour headsets, so I’d inquire with the CAF about guided tours with headsets. If you’d rather not deal with wearing a headset, I’d suggest trying their boat tours.
The last and best tour we took was the Bucktown/Wicker Park Food Tour with Chicago Food Planet. Food tours are wonderful because you get to sample food from various restaurants without having to spend a lot of money. The food that we tasted on this particular tour was delicious and generously portioned: George’s Hot Dogs gave us each an entire Chicago-style hotdog; Hot Chocolate offered a medium-sized cup of iced hot chocolate with a homemade marshmallow; The Goddess & Grocer handed out pasta salad, Piece dished out slices of handcrafted pizza and beer, Sultan’s Market served falafel pita sandwiches, and iCream scooped delicious frozen treats. You definitely won’t go home hungry after this tour! In addition to the food, I appreciated the tour guide’s thorough explanations about local architecture and businesses while walking through the neighborhood.
Please note that these tours are typically offered late Spring – early Fall; so if you’re visiting during the cold Winter months I’d recommend purchasing the Chicago CityPass where you get admission into five of the city’s most popular indoor attractions. Also, if you’re interested in art, admission is free at the Art Institute of Chicago every Thursday from 5 p.m. – 8 p.m. and the Museum of Contemporary Art Chicago is free every Tuesday.
Getting around town: The CTA is the best way to get around the city. CTA buses and trains can get you very close to your destination. You may buy 1-day, 3-day, 7-day, and 30-day transit passes online. If you’d rather purchase passes in-person, try the airport or grocery stores (Dominick’s, Jewel, etc.). To me, the easiest location to pick up a CTA pass is the currency exchange located on Chicago Ave. and Rush St. (close to the Chicago red line stop).
Language tips: Everyone in Chicago pretty much speaks English. But if you want to sound like a true Chicagoan, remember to exaggerate your vowels!
Other Advice: If you plan to fly to Chicago, arrive at the Midway Airport instead of O’Hare Airport. Flights are much cheaper to and from Midway. And, if you choose public transportation to get to your hotel, the El train’s orange line from Midway to downtown is more scenic than the blue line from O’Hare.
Another tip is to check out the Metromix Chicago website. Metromix has A LOT of event reviews and listings, so you’ll know what’s happening on the day, week, or month you’re visiting!
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