5 Days in Chicago-and Had the Time of our Lives!!!

We have a paper bag.

In the bag are slips of paper listing places that we would like to go on a 4-5 day fall adventure. Last October, after visiting our "bag destination" Napa Valley, we reached in and grabbed Chicago.

For the following year I researched the heck out of Chicago so that we could make the most efficient use of our time, and have a great trip. We did it!!!!

After looking at hotels that met our needs (walking to most places, breakfast included, good reviews)...I booked Hotel RIU Plaza Chicago.  We have stayed at all-inclusive RIU resorts in the Caribbean.  Although not one of our most favorites-this Spanish chain is relatively new to the market in the United States.  The hotel is only a couple of years old.  We know that they start out with "lower" rates-then after they are established and reviews are positive, they up the rates.  We stayed 4 nights and booked in November 2025 for our September 2026 trip.  The total went up $800 ($200 per night), then was sold out.  Book early...most hotels have a 48 hour cancellation policy.

As usual, we stayed overnight in Syracuse at Hampton Inn & Suites for our 6AM flight.  So nice to have them drop us at the door, then return for us on Friday.  Our car stays parked safely at the hotel.  We had direct flights to Chicago-which was nice.  Going early Monday AM and returning Friday PM is perfect for business travelers-and worked out great for us too!!

We were wheels up at 6:02 AM...snacks by 6:10.  We arrived by 6:40 (1 hour time difference) in Chicago (scheduled for 7:30).  Uneventful flight!

Once we arrived, we grabbed luggage and a taxi to the city.  We knew we were at rush hour time, and Uber and Lyft have surge pricing.  Our taxi driver was an Indian man named Sodhi who has driven in Chicago for 52 years.  Oh my!!!  As Al said...it was literally like being in a video game.  He would force his way from lane 1 to lane 5...exit, get back on...force his way to lane 1...and over and over for the ride.  It was 1 1/2 hours...to drive 18 miles!  Although it was a harrowing ride, he was safe enough-and we actually hired him to take us back to the airport (which took 25 minutes). 

It was raining when we got to the hotel, but after leaving our luggage we spoke to a concierge who suggested Wildberry Pancake Restaurant for breakfast.  Super easy to get to-but we were totally unfamiliar with the city so we were walking down Michigan Ave., trying to use GPS, looking at everything, trying not to run into people, and hoping to stay dry!!!  We knew there would be a wait for the breakfast place-but it was less than 5 minutes.  Incredible food, and an amazing start to the city!!

It stopped raining during breakfast.  The restaurant is right along Millennium Park, so we walked all over the park.  The park is absolutely gorgeous!  The highlight of the park is Cloud Gate..."The Bean".  It was so cool...and absolutely not to be missed. 

Underside of The Bean

The Flowers in Millennium Park were stunning 

Our goal that morning was to go to the Art Institute of Chicago around the 11AM opening time.  I had looked at the website and determined what we actually wanted to see.  We are into Impressionist Art, and have been to many art museums all over the world.  Going into an art museum without a game plan is a total waste of time.  You end up spending way too much time on stuff that you aren't interested in, then miss the good stuff.  For us...Floor 2 was the plan.  I actually had a list of paintings that we did not want to miss, and where they were located.  Obviously, we did see other art, but what we saw was exactly what we were interested in.  It is an amazing museum.  We bought tickets right at the door-but likely summer and weekends it would be harder to do that. This is a wonderful Art Museum...not to be missed if you are into art!

Our next activity was walking back towards the hotel to pick up an Architecture Boat Tour on the River-First Lady.  Lucky timing, we bought tickets about 5 minutes before the 1PM sailing. Harry was our guide for the 90 minute cruise on the River. It was great...we were right up on top in the middle.  I think we would have seated ourselves on a side if we had arrived early-but in retrospect the middle seats give the most visibility to everything.  You are always looking up at the skyscrapers...and they are just stunning.  People suggested that we do this the first day-and we are glad that we did.  It gives the overall view of Chicago, and we easily navigated the city-without GPS once we figured  out the lay of the land. 

The gorgeous St. Regis Chicago

I was working on adrenaline by this point-but Al was bushed.  We walked back to the hotel and stopped at Crushed by Giants Brewery for a flight.  We really liked the beer-but were actually too tired to even have a glass, just sharing a flight it was! We checked into the hotel for a brief rest, and to check out the room.

We were in Chicago for Chicagohenge-the time of year when the ball of the sun at sunset is directly between the tall buildings on a few streets in the city.  To get there...we needed to walk back down Magnificent Mile almost to the Art Museum.  Despite being totally tired, Al agreed to walk back down with me!! Unfortunately, the clouds won the day...and it was not a good sunset-but we tried.  I give Al all the credit in the world for making that walk back there (to see basically nothing...) We walked 9 miles that day/27 miles for our total trip!

This was all we could get for the day.  Those pesky clouds!

Not my photo...what "real" Chicagohenge is supposed to look like!!

Dinner that night was on the rooftop of our hotel.  It is gorgeous up there, with a glass floor extending out from the 27th floor of the hotel over the sidewalk.  It was a little chilly for eating outdoors, but the food was good.  It was 8PM...felt like midnight!!!

Tuesday our plan was to go to the Northwest side of Chicago for a Wrigley Field Tour. We started with an included amazing buffet breakfast at our hotel!! Figured out how to take the L Red Line (easy to get there, not crowded at the time we went).  There was a 10AM tour, and we got there 10 minutes before and bought a ticket at the door.  We knew there was another tour at noon if our transportation took longer.  Definitely always have to plan around time it takes to get places in a large city!!  The tour was amazing.  Brian was our guide and he was super funny, and of course a huge Cubs fan!

After the tour, I wanted to get a Chicago Hot Dog, since baseball and hot dogs do go together!! Trip Advisor and Google helped us find Wrigleyville Dogs...exactly what I wanted.  

Took the L back, and went to rest up at the hotel.  Had a drink at the lobby bar. Having traveled together for so long, we know that we can stay busy and see lots of things as long as we have a down time to relax.  I also stayed on my local time schedule by getting up at 6AM (usually 7 at home), and just relaxing and getting ready slowly to begin the day.  No jet lag at all for this trip!!

We had to go to the North of the city to go to our planned Broadway Theater show Jekyll & Hyde.  Went early enough to locate the place!! It was only a few blocks from the hotel.  I bought tickets several months early.  We were in Row B...paying NYC prices!!! Stopped off at the Harry Potter Store to look around.  Before the show we went to dinner at Gino's East to have Deep Dish Chicago Pizza.  It was close to the theater.  We did not preplan any dinners, but once we figured out the schedule I did look at places that might be options.  Pizza was great-loved the atmosphere!! The show was only OK.  Loved the singing, acting, and music...but the storyline was a bit strange for us.

Wednesday was our day to go to the Southside of Chicago.  We could have taken public transport-but decided to just get a Lyft.  He dropped us at the Griffin Science Museum.  We aren't interested in Science-but they have a special amazing Anne Frank Exhibit.  We have been to visit the Annex in Amsterdam-and this exhibit was much more complex and informative.  We bought tickets at the door-and were very pleased that Anne Frank was not an additional charge.  It originally was, but people complained so much that an anonymous donor donated the $$ to pay for September and October.  Hopefully that will be able to continue! Wandered a few minutes around the museum.  It is beautiful-but our grandchildren would enjoy it more than we did.

From there, we walked to the Obama Presidential Center.  After the emotional trip to Anne Frank, this just continued the smiles thru tears.  We did not have tickets to the museum itself...but somehow I just knew that what I needed to feel was not contained in those 4 walls.  The gardens and playground are beautiful.  There is a statue of Barack and Michelle Obama right outside the museum welcoming people to the museum.  There was a line waiting to see it to take pictures.  We stood in about a half hour line-I'm sure that it is much longer on weekends.  There was so much joy in that line.  Almost all were people of color...coming to honor the Obamas.  We laughed as everyone posed for pictures and just handed the camera to the person behind them to snap shots.  We took a lot of pictures for people-they took them for us.  What an honor!!!  Without tickets people are still able to go into the museum on the 1st and ground floor. We really wanted to see the painting of the Obamas...with Michelle placed thoughtfully in the foreground.  The entire center is intentionally done-honoring all humans, and reminding us that some (including people of color, indigenous persons, those with intellectual disabilities, and people with fragile financial situations) are needed and wanted in this space.  It was placed on the Southside for that very reason...and it was so obvious.  Loved all the art-and the descriptions of why that art was chosen.  A day that we will never forget!

We took Uber to Chicago Brewhouse on the Riverwalk.  Had a beer-and tried Chicago Italian Beef. Walked back to the hotel with no plans whatsoever for dinner-just knew that we didn't want to go too far.  I contacted 2 places nearby, which were both full-with only 9PM or later available.  We ended up booking at Volare.  #18 out of over 10,000 restaurants in Chicago-and it was so amazing, and our favorite place that we ate dinner-that we kind of just fell into!!  It was LOUD when we walked in-business workers, families, all trying to outtalk each other.  The typical Italian family-and yes, we did feel just like family!!!  Amazing homemade food/pasta, homemade limoncello...homemade dark chocolate gelato.  Wow!!  Carlos was our server, and he was simply awesome. I'll never understand how we lucked into this place-but it was the highlight of our dining experiences in Chicago. 

After dinner we went up on the rooftop of our hotel, and I bravely went out on the glass floor!!!  It was absolutely thrilling.  Al was not into it-but he took pictures!

Our final full day we walked out to Navy Pier.  We did ride the Centennial Wheel.  I loved it, Al went along for the ride-not his favorite!  We had Rainbow Cone...originally started in Chicago-so another Chicago iconic food...I think we tried all of the main ones!  Navy Pier is a beautiful walk near Lake Michigan.  From there we went to the Riverwalk and walked a bit more of that.  We went to City Winery for a glass of wine, ceviche, and hanging out sitting next to the river on a sunny day!

Before leaving home we bought tickets to another musical at Drury Lane Theater in Oakbrook Terrace...Buddy, the Buddy Holly Story.  We had seen it twice, and wanted to see it again. "Everyone" on travel forums told us that no one goes to Drury from the city.  It is 20 miles away...and let's be real, traffic is thick.  We didn't care-we wanted to see it!

Our Lyft ride was 1 hour and 20 minutes!!!!😒😒We had actually planned for it.  Dinner was at the theater at 5:00-Lucille.  We left at 3:30 (preordered Lyft) and arrived just in time for dinner.  Dinner was great-pricey, but great!  This theater is very upscale in a very upscale community.  However, every single staff that we met-or talked to prior to arrival was very, very kind and helpful.

Going home we quickly called a Lyft and we were home in less than 30 minutes!! Luckily, we have navigated enough large cities that we knew how to play the travel game effectively.

Friday we packed for home, had another great breakfast, and had Sodhi pick us up by 10:30 for a 1:30 flight.  He thought 11 would be good for pickup time-we were nervous from the arrival mess. We also had seen super long TSA lines on Monday as we left.  Turns out that he was right!! Not only was it a quick trip-but we literally walked thru TSA and got to our gate quickly.  We were able to check our bag outside the airport which was so nice. Now...they did move our gate 4 times, but that is to be expected.  I had upgraded us for this flight, and on the 1 hour 17 minute flight I enjoyed a complimentary glass of wine!!  The flight was uneventful, but we sat 45 minutes on the tarmac upon arrival in Syracuse because the plane parked at our gate had some issues that was not allowing it to move away from the gate.  The pilot was apologizing all over the place...stuff happens, we were parked just hanging out.  We were just fine!!!

Chicago was exactly what we were looking for.  A city that is easily navigated by walking if you stay center city.  We NEVER felt at all uneasy.  We were out at night-and that first night I was going to walk down to sunset by myself...in a city.  I absolutely would never walk in my city at dark.  There are a lot of tourists around, and we felt safe.  Now, there might be some pickpocket/stealing cell phones going on on the Magnificent Mile due to the large amounts of tourists-but we are always conscious of city savvy.  I would say almost every single tourist on the Magnificent Mile held a cell phone taking pictures (that would be me...), and so many were doing Tik Tok content videos.  It's a picturesque city...but it is a city, so be careful, and just use common travel sense!!

This is not mine.  It is from social media.  I would say that it accurately represents the heart and soul of this wonderful city.

Over the 5 days that we were in Chicago we met lots and lots of staff in different capacities.  We always chatted with them. Almost every single one was some kind of non-white ethnic person.  They were all excellent workers.  Recent trends have been to send agents to Chicago to weed out the "immigrants".  Personally, I have no idea how this city would continue without the workers that are there, doing the work, taking care of businesses.  We are hopeful that this practice comes to an end soon, and agents spend their time keeping us safe from people that actually are trying to do harm, not just trying to make a living for their families. 

What did we miss seeing?  Well, obviously Chicagohenge!!!  We were unable to do a stadium tour at the Chicago Bears Football Stadium.  That would have been fun-since they may be moving out of Chicago.  The availability was not there to visit at a time that worked for us.  We didn't do the Willis Tower/Sears Tower because we had a very nice view on our rooftop, and taking the Centennial Wheel gave us a terrific view. Other than that...everything worked out as we wanted. 

We always pick up a couple of kitchen towels from out travel.  Light to pack!!

Everything mentioned in this blog has been individually reviewed on Trip Advisor.  I will answer any questions or respond to any respectful comments.