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I have decided to write about my Chicago trip similar to how the New York Times reviews their 36 hour travel experiences. I am going to give you a day-by-day itinerary of how I spent my weekend in Chicago.


12:00 p.m. – We checked into the Courtyard Marriott Downtown/Magnificent Mile. The hotel’s interior is stylish and contemporary with large guest bedrooms. The hotel has an adjacent parking garage that seemed reasonable, $44 a day, along with a Starbucks, full-service restaurant, workout facility and large swimming pool. My main attraction to the hotel was its location, right near Nordstrom, Coach and other stores along Michigan Ave!

1:00 p.m. – Started our afternoon with a trip to Navy Pier. Navy Pier is Chicago’s lakefront playground. Situated on Lake Erie, the pier offers locals and tourists a place to eat, shop, drink and relax under the sun. We ate at Harry Caray’s Tavern, which is an American restaurant located right at the pier. Navy Pier also has a 15-story tall Farris Wheel that provides amazing views of the city, and it is affordable at $6.

6:00 p.m. – We went to Reggie’s Rock Club for the Timeflies/IanJ concert. The venue is a quick cab ride away from the Mag Mile area. I thought Reggie’s was a great place for a concert and I would definitely go back for another.

9:00 p.m. – Since we were in Chicago, we had to try the city’s famous deep dish pizza! Being only 2 blocks from our hotel, we went to Gino’s East for deep dish cheese and pepperoni pizza. Word of caution, the pizza takes an hour to bake so be prepared to spend some time waiting around for your dinner! However, it was well worth the wait! The pizza was delicious and extremely filling!


9:30 a.m. – Breakfast that is filling, healthy and delicious, go to Eggsperience Cafe in Chicago’s River North neighborhood. The prices were reasonable for being in the heart of Chicago and the portions were big enough that I did not even need lunch! I had Eleni’s Egg White Delight omelet and let me tell you, the word HUGE doesn’t even begin to describe how massive of a portion I got! The omelet is something that at least 2 people could share!

11:00 a.m. – Shopping on Michigan Avenue. The Magnificent Mile is filled with amazing stores to spend the afternoon strolling through! Nordstrom and Crate and Barrel were by far my favorite! They were both absolutely massive and filled with over 4 floors of stuff! This area was also great to walk around at night when it was lite up.

1:00 p.m. – If you have a sweet tooth like me, you MUST pay a visit to Sprinkles Cupcakes in Chicago’s Gold Coast neighborhood. The cupcakes are so delicious and fresh that you will leave wanting more! I tried the red velvet and raspberry chocolate and both were delicious!

2:00 p.m. – A must see spot for visitors is Millennium Park in Chicago’s The Loop neighborhood. It is filled with neat architectural and artistic structures, a venue for outdoor concerts and or course the famous elliptical, stainless steel structure in the park’s Could Gate area. This park is perfect for a sunny afternoon and not too long of a walk from Michigan Ave.

7:00 p.m. – Chicago has a huge range of steakhouses but one that I love and recommend is Tavern on Rush, located in the area’s Gold Coast neighborhood. Tavern on Rush is chic and sophisticated seafood and steakhouse that is in a very hip part of downtown. The two story restaurant features a stylish bar on the first level and glamorous dinning room on the upper level. Be sure to make reservations, though, because the restaurant is a very popular spot for on the weekends.

10:00 p.m. – End the night with a drink at Donald Trump’s hotel Trump Chicago in Rebar, the hotel’s sleek and uber-popular bar. Rebar is a place to be and be seen in Chicago. With views of the Chicago River surrounding the bar, it makes a beautiful ending to a long day. However, the drink menu is not inexpensive, so be ready to splurge.


9:00 p.m. – I am sure there are more unique breakfast places, but Jon and I stopped in to Panera for oatmeal and coffee because of it’s convenient location to the hotel. However, their steel-cut oatmeal was delicious!

11:00 p.m. – Drive by the original Playboy Mansion, which has since been converted into luxury, multi-million dollar condos. The mansion is located at 1340 North State Parkway, Chicago, IL 60610.