3-Day Chicago Itinerary

Escaping on a quick road trip to the Windy City of Chicago was such a great way to end the summer! Over 3 days, we explored the city – tasting & seeing all the main sites, including hanging over the ledge of the famous Willis Tower and exploring all the amazing museums! This 3-day Chicago Itinerary summarizes our adventures:

Chicago Skyline | Chicago Travel Guide | The Spectacular Adventurer

3 Days in Chicago

Similar to other city guide (see Seattle Travel Guide), we like to stay in the downtown central area so we can make the most of our time in the city. This trip was no exception. We choose to stay at the beautiful and historic Palmer House – Hilton Hotel. Not only was this hotel within walking distance of most of the main attractions (a total must for me!), it had a great roaring 20s vibe. From lavish grand staircases to golden decorated parlors, it was like stepping back in time every time we walked in the doors. It was a great escape from the bustling city; however, with only 3 days to explore we rarely were at the hotel …

Chicago Buckingham Fountain ... 3-day Chicago Itinerary ... The Spectacular Adventurer

Day 1 – Millennium Park & Chicago Museums

If you missed it, the complete post of day 1 can be found here

On our first day, we explored Millennium Park, Cloud Gate, & the amazing Chicago museums. We set out early (before 8AM), to explore Millennium Park which was just down the street from the Palmer House. We first stopped at ‘Cloud Gate’ or better known as ‘The Bean’.

Cloud Gate in Millennium Park | Chicago Travel Guide | The Spectacular Adventurer

We then headed out to explore all the famous museums in the city, our first being the Art Institute of Chicago (~$25 for an adult ticket) that was located within the park. After marveling at the famous art works, we headed to the Field Museum and Shedd Aquarium (~$40 each for adults). Both were extradorinaiy and we easily could have spent half days exploring each. After the museums, we headed for dinner at the famous Lou Malnati’s for some deep dish Chicago pizza.

Chicago Field Museum | 3 day Chicago Itinerary | The Spectacular Adventurer

Day 2 – Walking Around Chicago

If you missed it the complete post of day 2 can be found here

Our second day within the city we set out to explore the Magnificent Mile, Navy Pier, and the Hancock Tower. We got a later start to our day (~9AM) and headed along Michigan Avenue to window shop along the Magnificent Mile. From Michigan Avenue, we headed toward the waterfront and arrived at Navy Pier. We loved walking around the area or the pier and the more residential area along the waterfront.

Navy Pier ... 3-day Chicago Itinerary ... The Spectacular Adventurer

We then headed for the Hancock Tower to take in more amazing views of the city via the restaurant. There we grabbed a snack and a drink while enjoying the spectacular views! After spending a while at the Hancock Tower, we headed to dinner at this amazing Italian place in Chicago – La Storia. It was a great end to our second day in the city.

Day 3 – Chicago River Front

If you missed the complete post of day 3 can be found here

On our last day of our 3-day Chicago Itinerary, we set out to explore along the Chicago river front. We took a boat tour along the river & stepped over the ledge of Willis Tower. To start the day, we went to the best brunch in Chicago – Fremont. From their amazing omelettes, bottomless mimosas, and tasty donuts, we were completely full by the time we left. After brunch, our next stop of the day was a tour along the river with Wendellas boat tour (tickets are ~$40).

Our last stop of the day was Willis Tower (tickets are ~$25). Here we payed to go up to the 103 story observation deck & step onto the ledge to see the streets below. Last, no trip to Chicago would be complete without a traditional Chicago Hot Dog. As our final day was coming to an end, we enjoyed this tradition on our way to our hotel.

If you enjoyed this 3-day Chicago Itinerary, you might also enjoy: Chicago Travel Guide and Seattle Travel Guide



  1. September 9, 2019 / 8:40 pm

    Love Chicago! Dinner and drinks at Hancock Tower is so much fun.

    • Liz
      September 9, 2019 / 8:42 pm

      Me too!! The View from the Hancock Tower is my favorite!!!

Leave a Reply

Your email address will not be published. Required fields are marked *