Top Things to Do in Chicago

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Chicago Questions and Answers

1. How do I get around in Chicago?

Chicago is a pretty large city but also boasts of the second-largest public transit system in the country - the CTA (Chicago Transit Authority). The CTA runs both the train lines (popularly called the ‘L’) and the bus routes. Then there is Metra Rail, the high-speed commuter train that connects the suburbs to downtown Chicago. So public transit should be able to get you anywhere you'll need to go while in Chicago. You can also taxis, water taxis and ridesharing services like Uber and Lyft.

2. What are the best things to do in Chicago?

There are loads of exciting places to visit and fun things to do in Chicago. You could try and squeeze all of them into one experience by booking the Go Chicago Explorer Pass or Chicago CityPASS. You could also book tickets for the Big Bus Chicago Hop-On Hop-Off Tour or Chicago City Sights Helicopter Tour. River cruises like the Lake Michigan Sightseeing Cruise and the Chicago Architecture River cruise are other fun things to do in Chicago. For great views, the Skydeck , located on the 103rd floor of Willis Tower (formerly Sears Tower) and 360 Chicago (formerly John Hancock Observatory) are both must-visit places in Chicago. Millennium Park, Navy Pier, and the Chicago Lakefront are other interesting places to see in Chicago.

3. Which are the best places to go shopping in Chicago?

The entire city of Chicago offers excellent shopping experiences. The mile-long stretch popularly known as the Magnificent Mile is chock-full of departmental stores, shopping malls, branded stores, and upmarket boutiques. Oak Street is the best place to find a large number of designer boutiques, especially French and Italian labels. The Loop is also a great place for shopping in Chicago, especially along State Street. One of the largest department stores in the world, Macy’s is located on State Street. For sidewalk sales and indie shopping, you can’t beat Andersonville. Another upcoming shopping area is Wicker Park and Bucktown, especially if you are looking for hipster fashion choices.

4. Is Chicago safe for tourists?

Despite its worrying reputation as a crime capital, Chicago is generally considered safe for tourists. Especially if they stay away from troubled spots like certain stretches on the South and West Sides. Most areas frequented by tourists, like those around the Loop and north of downtown are pretty safe. Tourists are advised to follow basic safety measures to minimize the odds of anything going wrong.

5. Which are the best places to stay in Chicago?

The best place for travelers to stay in Chicago would be in and around the Loop District in downtown Chicago. This is where you'll find most of the sights and attractions of Chicago. The area popularly known as Magnificent Mile gives you access to the best shopping as well as easy access to Oak Street Beach. If you are looking for peaceful and secluded Peaceful and secluded is a good choice. You could also try finding accommodation near McCormick Place – isn’t far from downtown, yet feels away from the hustle and bustle.

6. Which are the best places to eat in Chicago?

While Chicago is most well-known for its deep-dish pizza and loaded hot dogs without ketchup, it also boasts a bustling restaurant scene with both high-end restaurants and inexpensive street food and a variety of cuisines. Freddie's Pizza and Sandwiches is famous for its quintessential Chicago foods - Chicago-style hot dogs and pizzas. If you feel like a fancy brunch, you could go to the Margeaux Brasserie a French-inspired restaurant inside the Waldorf Astoria. Smoque BBQ, Harold’s Chicken Shack, Irazú, Rajun Cajun, Passerotto and the Chicago Diner are some of the other best places to eat in Chicago.

7. When is the best time to visit Chicago?

Summer (June-August) is by far the most popular time to visit Chicago but also tends to be the most expensive time to visit if you aren’t all that particular about the weather, you would do well to visit Chicago in spring (April to June) or fall (September-November).