How To Spend 2 Days In Chicago

After visiting some of the best cities in the world I honestly didn’t expect Chicago to compare… how wrong I was. Perhaps it was naive of me to think this, after all, Oprah does live there! But none the less, I was pleasantly surprised to find that Chicago was a city packed with some of the best food, culture, art and architecture.

I only spent a few days in Chicago, but made the most of my short trip. This itinerary is filled with ideas and inspiration in case you also find yourself trying to pack this huge city into 2 days.

Day 1

Millennium Park

Start your day by visiting Millennium Park, which is free to walk through. Depending on the time of year, you can easily spend hours walking through this park, which is home to the famous bean. Don’t rush through your time at Millennium Park or you could miss some of it’s other attractions like the Jay Pritzker Pavilion, Crown Fountain,Wrigley Square, Boeing Galleries, or Frank Gehry’s BP Bridge.

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A Famous Chicago Hot Dog

For lunch, try a famous Chicago hot dog (a beef frankfurter on a poppy seed bun, topped with yellow mustard, white onions, relish, a dill pickle spear, hot peppers, and tomato wedges). If hot dog’s aren’t your thing try a famous Chicago beef dip sandwich (thin slices of seasoned roast beef, on a Italian-style roll dipped in au jus).

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If you’re looking for a classic Chicago experience, spend your afternoon at the Willis Tower, formerly known as the Sears Tower, the tallest building in the Western Hemisphere. For $22 USD per adult you can visit the Skydeck and feel your heart drop as you step onto the glass ledge and take in the spectacular Chicago views. Just beware that getting up to the Skydeck can take hours in line followed by a long wait to step onto the glass ledge.

If the Willis Tower doesn’t interest you, spend your afternoon at one of Chicago’s many museums, like the Art Institute of Chicago or the Shedd Aquarium, or just explore the fascinating streets in the downtown core. I enjoyed going into the lobby’s of the office buildings, where visitor’s are often welcomed to come in to view the history and architecture.

If you’re in Chicago for baseball season, you can even spend an afternoon at a baseball game rooting for one of Chicago’s 2 teams, The Cubs or the White Sox.

Gino’s East

For dinner make sure you try some famous Chicago deep dish pizza. I loved Gino’s East, which had gluten free options.

Day 2

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Begin your day at Navy Pier, and enjoy walking up and down the pier and taking a ride on the ferris wheel or other carnival rides. There are a lot of good and quick restaurants in this area for lunch, at various price points.

Michigan Avenue – Garrett Popcorn

Spend your afternoon walking up and down Michigan Avenue, one of the best streets to shop and take in the city. I’m not going to lie, I spent all my shopping money at Garrett Popcorn, which sells a Chicago classic, gourmet cheese and caramel popcorn (sound disgusting, tastes delicious), made famous by Oprah.


Glenn’s Dinner – Image Source:

There are many famous restaurants in Chicago to try for dinner. If you’re looking for something unique venture uptown to Glenn’s Dinner, which was featured on the TV show Diners, Drive-Ins and Dives. Glenn’s Dinner is known for it’s delicious seafood, but also weirdly has EVERY cereal imaginable, which a lot of people were ordering for dinner!

Architecture River Cruise

Just before sunset, head back downtown and take an evening architecture river cruise. This was the highlight of my time in Chicago because the architecture of the buildings is world renowned and so unique. Although, you can take this tour during the day, the evening cruise allows you to see the city against the sunset.  There are many different companies that offer this tour, and the price is approximately $45 USD per person.

Note: This tour is only available from April-November. Also, if you plan your tour in advanced, some of the tours have fireworks.

Chicago has a lot to offer and it’s nearly impossible to see it all in just 2 days, but hopefully with this itinerary as your guide you’ll feel like you really experienced this great city.

Have you been to Chicago? Let me know how you made the most of your time there in the comments below.


18 Comments Add yours

  1. The Chicago hotdog looks very tempting! Wow! Looks like we have to pay special attention to our weight if we visit Chicago!

    Liked by 1 person

    1. Jessica Lim says:

      Yes if I was there for more than 2 days my weight probably would have been in trouble haha!

      Liked by 1 person

  2. Thank you for an accurate and insightful review of Chicago. Your photos are very impressive, especially the one of Marina City at sunset from the evening tour.

    Another enticing museum is the Chicago History Museum, with a wide variety of exhibits, some permanent and some temporary. The fashion exhibits are always first rate, and seem to be done about every other year, with one coming later this year. If you want to look at the books from past fashion exhibits, peek at those in their shop. Perhaps your library even has a copy. The CHIC CHICAGO exhibit/book is tops.

    Liked by 1 person

    1. Jessica Lim says:

      Thanks for your comment! I wish I was able to go to some of the museums while I was there so I will have to check out your suggestions for next time.

      Liked by 1 person

  3. I’m so glad you enjoyed Chicago. You are right, there is too much to see it all in two days, but you certainly found a lot of the highlights. The architecture tour on the river is certainly a must. I would add that garden lovers visiting Millennium Park should take time to see the Lurie Garden. For people who have extra time, I might suggest visiting some of Chicago’s neighborhoods: Pilsen, which is like a slice of Mexico City that has become a magnet for artists: Devon Avenue, which has the biggest concentration of South Asian businesses (including lots of good restaurants) in North America. Hyde Park, around the University of Chicago, has interesting architecture and shops and also a couple of excellent but lesser known museums: the DuSable Museum of African-American History and the Oriental Institute. Oh, and we have two good-sized Chinatowns: one on the north side on Argyle, and one on the South on Cermak near Sox Park

    Liked by 1 person

    1. Jessica Lim says:

      Great suggestions! I would have loved to see some of those neighbourhoods and both of the Chinatowns. I guess I will just have to go back.


  4. kateamirault says:

    Great post. We love Chicago. You did many of the things we did a few yrs ago. When Oprah had a studio there that was cool too. Great food everywhere and music. It’s a great American city with lots of diversity & intriging elements. Glad you enjoyed it!

    Liked by 1 person

    1. Jessica Lim says:

      I would have loved to have gone when Oprah had her show there! Thanks for your post!

      Liked by 1 person

  5. I am not a ‘city’ person and prefer wide-open spaces, but I absolutely fell in love with Chicago. I didn’t sit in the Willis Tower boxes as comfortably as you did, though. 🙂 Beautiful city with friendly people, and a place I know I’ll definitely visit again. Awesome review and photographs. Safe travels!

    Liked by 1 person

    1. Jessica Lim says:

      I’m actually the exact same, I love living away from the big cities but love visiting different cities around the world. Thanks for your comment!


  6. I’m a Chicagoan so I’m happy you had fun while you were here.


  7. I spent about 2 days in Chicago last winter. It was freezing, but a lot of fun. The art institute was great and Gino’s east was probably the highlight of the trip. Since my fiancé is a big Chicago sports fan we saw the Blackhawks and bulls play as well.


  8. Globetrotter says:

    The hot dog and pizza look amazing! This is a really good guide for touring the 2nd city! I will be sure to use this one too in my travels there.


  9. I went during winter of 2013, I absolutely loved the museums and the vibe of this city. Uno ‘s pizza are crazy and typical of Chicago I liked it a lot.


  10. Great post! I also really love your blog. So many inspirational travel stories! Thanks for the recent like on my Art in Bloom post. Follow for follow?


  11. Thanks for the gluten-free suggestion!!


  12. ramblingjed says:

    I liked your Chicago post. It was very unique. I went to the Bean and the Willis Tower, but not the others. Next time I will try your other stuff.


  13. Reblogged this on Journal Edge and commented:
    Article/ Image Source:
    Must Read this amazing blog post 🙂


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