Going To Chicago? Here’s A Free 3-Day Itinerary
This summer, I was the stereotypical tourist in Chicago. Here’s what I did in 3 days.
Where I Stayed
The Pendry is within walking distance of major tourist attractions like, the Chicago Riverwalk, Millennium Park and “The Bean.” There’s a fabulously cozy rooftop restaurant with a stunning city view, and a downstairs breakfast cafe made for people watching.
Scroll to the bottom for a downloadable itinerary!
Places To Visit
- Chicago Riverwalk
- Millennium Park
- “The Bean” aka Cloud Gate
- Lurie Gardens
- Art Institute of Chicago
- Crown Fountain
- Skydeck Chicago at the Willis Tower
- “Chicago Observatory” aka 360 CHICAGO
- Magnificent Mile
- The World’s Largest Starbucks
Things To Try
- A deep dish pizza
- A Chicago dog
- Chicago River Architecture Tour
Day 1
I landed in Chicago at 1:15 pm. It took about 50 minutes to get to my hotel, and the cost was nearly $60.
While we waited to check-in, we had lunch at Venteux, a French restaurant in the Pendry. We shared oysters and sipped on Spritz.
After lunch, we crossed the historic DuSable Bridge, staring up at the beautifully, odd buildings looming around us. We bought tickets for the 90-minute Chicago River Architecture Tour, and it was one of my favorite moments of the trip.
- Even if you aren’t a fan of architecture, the buildings along the Chicago riverwalk are deceptively stunning. Again, it was a summer evening, so we watched the sunset, peaking around building corners. Cool river air blew past us as we took pictures.
After the boat tour, we went to the Navy Pier. In the summer, there are fireworks every Wednesday and Saturday at 9 p.m.
I made dinner reservations that we ultimately skipped. Instead, we tried a deep dish pizza around our hotel and watched Rush Hour on cable. As a hand-tossed or thin-crust pizza lover, I actually liked the pizza more than I imagined. So many layers of pepperoni and cheese!
Day 2
We woke up early the next morning to have breakfast at Wishbone. Delicious! They serve coffee and liquor. That’s my type of place.
It was a short, neighborly walk to Millennium Park.
- First, we took pictures of ourselves and the skyline at “The Bean” aka Cloud Gate. There are restaurants and shops nearby. We tried our first Chicago Dog, eating the colorful concoction on a park bench.
- Next, we found the Lurie Gardens. Butterflies and dragonflies hang around these ginormous, wild flowers. It’s a hidden oasis in this busy city. There are shaded sitting areas to lose track of time in.
The Nichols Bridgeway connects Millennium Park to The Art Institute of Chicago. It’s a convenient, breezy walk across the silver bridge. I highly recommend.
- Tickets for out-of-state visitors are about $35. I also bought an additional ticket for one of the special exhibits they were having at the time.
- The museum is massive. You can definitely spend the whole day staring at the art. I loved the sculptures and the modern art.
We left the museum in the late afternoon. Before walking back to the hotel, we splashed around in Crown Fountain. Children running, screaming, squealing, and playing drowned out the city. There are food trucks nearby, so I had an ice cream and just sat.
That evening, we booked a Chicago River Dinner Cruise. It was really expensive, so I wouldn’t recommend. But we were out on the river all night — we ate dinner and drank (weak) cocktails, staring out at the city. We saw the Chicago skyline light up, and for that, it was worth it.
Day 3
One thing about Chicago: the city loves heights. After a mimosa and a latte, we spent out last day in the sky. Our first stop was the Skydeck Chicago in the Willis Tower.
- I bought three tickets for about $120, and I picked the time slot.
- Each group has (I think) a minute and a half to stand on the clear skydeck and take pictures. But you can get back in line as many times as you want. The line moved quickly, too.
- I was too busy snapping pictures to be scared of the height. But I did look down for a few moments, and even thinking about it now, gives me the chills.
Next, we ate at a restaurant nearby until it was time for the Chicago Observatory, or 360 CHICAGO.
- I paid around $140 for three tickets. This observatory wraps around the building, overlooking the entire city. You watch traffic move, people sitting on rooftops, boats floating off in the distance.
- There’s also a bar to order drinks from. I bought three drinks, so that was also included in my charge.
For the rest of the evening, we walked down the Magnificent Mile. We visited the world’s largest Starbucks and tried sugary sweets.
Dinner was at the Chateau Carbide at the Pendry. It’s an intimate, cozy lounge that was the perfect finale to a long weekend.
