May 31, 2018

Chicago, Illinois | Adventures

Chicago will always hold a special place in our hearts.  So many incredible places to see and things to do and people to visit!  When we make travel plans, we meticulously plan out each detail making sure to not miss out on any iconic stops the city has for us.  Well…Anna does.  Shane prefers to relax and take things as they come as we travel.  So we compromise.  Anna plans.  Shane chooses which of the activities to do that day and which to skip!  Win-win!  Here is what our 3 day itinerary looked like for our trip to Chicago, all of which we highly recommend!:

Day 1:

  1. Drive to Chicago (about 6 1/2 hours) with a stop in Wisconsin Dells for lunch.
  2. Purchase Transit Passes upon arrival & check into Hotel – Best Western River North – best value in the area!
  3. Eat dinner at Rosebud Trattoria – the food was amazing!
  4. Explore Navy Pier & ride the  ferris wheel – the view of the city lights and the water glistening in the moonlight was like nothing else!
  5. Stroll along the Riverwalk on the way back to our hotel for the night.


Day 2:

  1. Eat breakfast in the hotel.
  2. Visit family & friends along Huron Street, do a little shopping and take some time to photograph the city as we walked the streets of Chicago.
  3. Eat lunch at Lou Malnati’s Pizzeria – CLASSIC Chicago deep dish pizza!
  4. Explore Oak Street Beach – this place is amazing and we loved the beach vendors, the street artists, and the men playing chess along the edge of the walk.
  5. Spend some time shopping complete with a stop at Burton (for Shane).
  6. Tour John Hancock Center/360 Chicago – the view was absolutely worth the price of the tour!
  7. Eat dinner at the Cheesecake Factory – a favorite of Anna’s!
  8. Explore the Magnificent Mile of shops and see the Chicago Harbor Lighthouse.
  9. Experience sunset on the Wendella Lake & River Architecture Tour – perhaps our highlight of the trip!
  10. Walk back to the hotel for swimming and late-night snacks on the hotel rooftop.


Day 3:

  1. Eat breakfast in the hotel.
  2. Take the L Train to see Cloud Gate (better known as the Bean) in Millennium Park.
  3. See Buckingham Fountain & bask in the sun watching the sailboats & seagulls.
  4. Eat Lunch at Portillo’s with friends!
  5. Check out of our hotel & stock up on a few souvenirs before heading back home through Wisconsin.