Chicago, Illinois - July 2nd to 5th, 2026

We spent four nights in Chicago before starting Route 66. That gave us three full days to explore Chicago, both for Route 66 related places of interest and other non-Route 66 places.

Thursday we drove from Rock Island in Illinois to Chicago. It was about a three hour drive. Our only stop for the day was at a Love’s Travel Center, about half way. We spent a little extra time hanging out at Love’s, because we didn’t want to get to Chicago too early. Our reservation at McCormick Place Lot B would not allow us to enter the Bus/RV/Marshaling area until 3 pm.

Even though our reservation to park Red Tail in Chicago would allow us to sleep in our RV, we made a last minute reservation at a Hampton Inn in McCormick Place, about a half hour’s walk from the parking lot. The heat wave we were experiencing gave us second thoughts about sleeping in the RV in the middle of a sea of black top with no amenities.

Before we left the campground in Rock Island, we dumped our gray tank and our cassette. We did not refill our fresh water tank, since it will be sitting in the hot sun for four days while we’re in Chicago. When we stopped for lunch at Love’s, we tried to eat all the food in Red Tail that might not last four days. Even though we don’t like to put bread in the fridge, we put our loaf of bread and package of tortillas in the fridge this time. It’s better than letting the mold grow.

Driving into Chicago went much smoother than we were expecting. Most of the heavy traffic was heading the other direction and McCormick Place Lot B is pretty easy to reach from I-55. The hardest part was figuring out which of the two entrances to enter the parking lot. Everyone seems to call it Lot B, but RV’s are supposed to enter at the gate called Truck Marshaling.

Our bar code on Ann’s phone wouldn’t scan. A guy came out of the office and said if that happens, just push the button for a ticket and go in. We guess we’ll just need to resolve the issue when we leave. We parked at the northern end of the lot, next to a few other RV’s, then packed up what we would need for the next four days.

Walking to Hampton Inn from the parking lot was rather interesting. We started out by following Google Maps, but noticed signs that said Pedestrian Entrance Gate 23. It looked like Google Maps wanted us to go beneath the building on a road, but it was near the pedestrian entrance to the building, so we walked inside instead.

McCormick Place is a large convention center, with several convention buildings along with attached hotels. When we walked inside, the large expansive space looked empty. The only person we saw was a security guard walking towards us. So we asked him for directions. We told him we were trying to get to the Hampton Inn. He asked if we wanted to walk inside or outside. Well, given the heat outside, of course we answered “inside, if possible”.

The issue with Google Maps directions, is that it is two-dimensional, not three. So it didn’t really show that we needed to go up to the third floor of the convention center to get over the train tracks of the Metra. Then we went back down to the first floor only to go back up to the third floor to reach the sky bridge over to the Skyline Ballroom. Going around the far side of the ballroom brought us to another sky bridge over to the Hampton Inn. It was about a 15 minute walk, all inside.

The Hampton Inn was unusual in that the same building housed not only a Hampton Inn, but also a Home2 Suites and a Hilton Garden Inn. From the lobby on the first floor, you just picked the right bank of elevators to go to the appropriate hotel room. Then there was a fourth bank of elevators to go up to the roof top bar.

After checking into our room, we headed out for dinner. Just a few blocks away was Chicago’s Chinatown. We walked up and down Wentworth Avenue, stopping at Legend Dumpling + Bao to eat. It was a counter order place, but that was fine with us.

We ordered a couple of cucumber salads, an order of pork with cabbage Bao, an order of chicken Bao, and pork with green pepper dumplings. The Bao and dumplings could be ordered either steamed or fried. We chose steamed for the Bao and fried for the dumplings. The cucumber salad was a little spicy. It seemed like it was prepared with cilantro and perhaps rice vinegar. We’re not sure what gave it the heat.

There were several dipping sauces to choose from. One was really spicy, so we stayed away from that one. Another was sweet with a strong flavor of ginger. We used that for our Bao. Bao is a fluffy bread that surrounds a meatball center. We’ve had Bao before where the bread was just folded in half around the meat, but these Bao were completely enclosed, more like a dumpling.

The dumplings were smaller than the bao. An order of dumplings included 12 pieces, while an order of bao included two pieces. A friend of ours introduced us to a dumpling house in Colorado. She explained that the traditional way to eat them was with vinegar and thin slices of ginger. The dumplings we had in Colorado were steamed, but we dipped these fried ones in vinegar. We didn’t see any ginger, but we didn’t ask for any, either. But everything was pretty tasty, even without the ginger.

For dessert, we walked across the street to the Legend Tasty House. Their specialty is Thai rolled ice cream. We’ve had rolled ice cream before, in Destin, Florida (Fred Gannon Rocky Bayou State Park, Florida - March 22nd to 25th, 2023). The cream is poured over a chill plate where it is worked while it freezes. It is flattened out and then scraped up into rolls. It is an interesting process to watch. Ann ordered the Legend Storm which was passionfruit and dragon fruit, topped with whipped cream, mango, and small cookies. She could have added other mixins or toppings, but chose to keep it as is. Keith skipped dessert. Ann’s was very refreshing.

After returning to the hotel, Keith headed up to the roof top bar while Ann went for a walk, She still hadn’t closed her rings yet for the day. She walked back through the convention center in order to stay in the air conditioning. When she reached the point where we had entered the center earlier, she continued on over yet another sky bridge over highway 41 to the Lakeside Center. The Lakeside Center looked pretty deserted, but Ann walked through the building and out a door on the far side. She was on a terrace overlooking the Lakefront Trail and the Lake of Michigan.

Unfortunately, Ann could not get back in the door she came out. Uh-oh! How was she going to get back over highway 41? She walked around the Lakeside Center building, along the terrace, and saw there was an outside pedestrian bridge right next to the sky bridge. On the other side of the bridge was an open door back into the convention center. OK, crisis averted.

Upon returning to the hotel, Ann joined Keith up at the roof top bar. There were nice views from the roof, even nicer than the ones from our room. We had picked out a room on the top floor, hoping we might be able to see the 4th of July fireworks from there. However, some of the surrounding buildings are taller than our hotel, which may block our view.

We started out Friday walking the lake front up to Navy Pier. After walking through the convention center inside, we picked up the Lakefront Trail. The pedestrian portion of the trail is 18.5 miles long while the separated bicycle trail is 18 miles long. It runs from Kathy Osterman Beach in the north down to the South Shore Golf Course and Beach in the south. We were only on about four miles of the trail.

We walked past several boat docks, marinas, and yacht clubs along the way. It was Friday, the start of a holiday weekend and people were loading their coolers, towels, and toys onto boats to spend the day or weekend out on the lake. There were boats anchored in the harbor with slides, floating islands, and groups of people enjoying the water and each other.

Just past Shedd Aquarium, we stopped at a little food stand to get some watermelon and drinks. The weather was still hot, but only in the upper 80’s, avoiding the 90’s we had been experiencing. We found a spot in the shade on the grass to enjoy our treats and watch all the people.

By the time we reached the end of the Navy Pier, we had covered 4.2 miles, with an elevation gain of only 144 feet which we completed in one hour and 50 minutes. Even though it wasn’t exactly a hike, it was on a named trail, so we counted it as hike number 9 of our 52 Hike Challenge for 2026.

When we reached the Navy Pier, we walked the full length of it, first inside, then outside on the way back. The pier is full of shops, places to eat (both fast food and sit-down restaurants), a hotel, a children’s museum, and a maze. Up on the second floor were carnival rides, including a large ferris wheel. At the end of the pier, people on jet skis were trying to jump the wakes of the other boats speeding by.

We stopped to enjoy some lunch inside at one of the food courts, taking advantage of the air conditioning. Ann opted for the Chicago Italian hot beef sandwich from Chef Ciccio, Beef-Balls-Beer. Keith got a Chicago hot dog from AD&B (America’s Dog & Burger). The hot beef sandwich was very flavorful, with a couple of seasoned potato wedges on top along with a generous amount of juice. The juice drenched the bun, so that eating it required using a fork. It was tasty, but we would not recommend it for people who are on a low sodium diet. Keith liked his Chicago dog, but he felt it was not as good as the one he had last year at Portillo’s during our Amtrak layover (Amtrak: Denver to Ft. Lauderdale - March 3rd to 6th, 2025).

As we were leaving the Navy Pier, we just happened to come across the new sign for the start of Route 66. We had heard that they recently changed the start of Route 66 to the Navy Pier, but we weren’t sure if there was a new sign for it yet. Traditionally, the start of Route 66 was at the corner of Adams Street and Michigan Avenue. We’re not sure how the new route is supposed to go from Adams Street to the Navy Pier, as U.S. Route 66 never went past Michigan Avenue before. Needless to say, we will be starting our drive on Adams Street at Michigan Avenue.

After lunch, a thunderstorm came rolling in. We tried to make it from Navy Pier over to Ghirardelli Ice Cream and Chocolate Shop. We didn’t make it. The sky let loose and we were drenched, even with rain jackets and one umbrella. We ducked into a doorway for a few minutes and checked the forecast. It was not going to let up for a while, so we just pushed on in the rain.

Ann has a hard time passing up a hot fudge sundae from Ghirardelli. However, they seem to be getting more expensive and smaller in size. Somehow they just didn’t seem as good as Ann remembered them to be.

By the time we finished our sundaes, the rain had stopped. So we crossed over the Chicago River and hopped on the next boat tour with First Lady, one of the boat tour operators situated right along the Chicago Riverwalk. The tour was an hour and a half architecture tour up and down the Chicago River.

Our guide was a volunteer and an architect. He was very interesting. We learned about different architectural styles, skyscraper history, architectural challenges, and some general Chicago history. It was a great way to relax and tour Chicago.

After the tour, we headed down towards the Berghoff Restaurant where we had dinner reservations for 6 pm. Along the way, we stopped off at the Cloud Gate sculpture in Millennium Park, otherwise known as “The Bean”. We also saw it during our layover in Chicago a year ago. Only this time there were a lot more people around. Just south of the Bean is the Crown Fountain. There were a lot of people, especially kids, playing in the water of the fountain, cooling off from the heat. However, the thunderstorm had lowered the temperature to a more pleasant range.

The Berghoff Restaurant is located on Adams Street, otherwise known as U.S. Route 66. We had a little more time to kill before our dinner reservation, so we went to locate the old Route 66 start sign. It wasn’t hard to find. Adams Street is a one way street, so this is the start if you are taking Route 66 east to west, or starting in Chicago. If you are starting Route 66 in California, going west to east, then you will end on Jackson Drive, another one way street but in the opposite direction, just one block south of Adams. So we walked over to Jackson to get a picture of the end sign for Route 66.

The Berghoff opened in 1898 as a brewery by Herman Berghoff, a German immigrant. During Prohibition, the brewery became a restaurant with authentic German fare and Berghoff soda pops. In 2018, a brewery, called Adams Street Brewery was added back. The restaurant and brewery are still in the family, being operated now by third and fourth generation Berghoffs.

To eat, Keith ordered the Sausage Trio: bratwurst, knockwurst, and smoked Thüringer with sauerkraut and German potato salad. Ann had the Wiener Schnitzel with spätzle (an egg dumpling). She substituted red cabbage for the creamed spinach, as red cabbage is one of her favorite German side dishes. The food wasn’t the best German food we’ve ever had, but we’ve eaten a lot of German food over the years. We can definitely say that the dishes were pretty authentic German.

For dessert, we enjoyed the apple strudel with a scoop of ice cream. The strudel was pretty authentic as well, not too sweet and made with golden raisins.

After dinner, we decided to take the Metro train or “L” train back to the hotel. From Berghoff, our hotel was about a 45 minute walk and we had enough walking by this point. The Green Line train is only about a ten minute ride from Adams & Wabash to Cermak-McCormick Place. The Green Line station was just two blocks west of our hotel. It was easy enough to ride the train. We just swiped our contactless payment when we entered the gates at the train stop. We believe the charge is $2.50 every time you ride, no matter how far you go. When you use contactless payment, it charges you $5, then doesn’t charge you the second time you swipe that day. On the third swipe, it charges you another $5. So if you ride an odd number of times, you are overcharged by $2.50. We didn’t mind that for the convenience. Then we found out later, after we had ridden the L train multiple times in a single day, that if we bought a ticket at the vending machine or used the Ventra phone app, we could have purchased a day pass for $5. Oh well, live and learn. Not a big loss.

We spent most of Saturday in Oak Park, a suburb of Chicago. Oak Park contains the Frank Lloyd Wright Historic District which is where the famous architect’s first home and studio are located along with several houses and a church that he designed.

To get there, we took the Green Line L train to the Oak Park stop, the second-to-last stop of the Green Line. From there we walked about three quarters of a mile to reach Frank Lloyd Wright’s Home and Studio. We had no problems getting tickets for the next guided tour of the inside.

The inside tour was very interesting. We’ve been to a few other Frank Lloyd Wright locations, such as Taliesin in Wisconsin (Wisconsin Dells, Wisconsin - July 7th to 9th, 2021) and Taliesin West in Arizona (Lost Dutchman State Park, Arizona - September 17th to 20th, 2023). However, we learn something new about the man and his work each time.

We also bought tickets for the self-guided audio tour of the neighborhood. But it was about 12:30 pm by the time the guided tour ended and we were hungry. So we walked down to Lake Street for lunch. Our tour guide recommended the Little Gem Cafe for upscale dining and the Jerusalem Cafe for a budget conscious option. When we walked by, it didn’t look like the Little Gem was open, so Jerusalem Cafe it was.

Ann ordered the gyro sandwich with rice while Keith opted for the falafel sandwich with French fries. The food was pretty decent and filled our bellies.

Back at Wright’s Home and Studio, we picked up our audio guide devices and went on the walking tour. The tour led us by six homes along Forest Avenue and Elizabeth Court that Wright designed. The homes are all privately owned and occupied, so we could only see the homes from the street, but the commentary was very informative. The Wright homes are surrounded by many other large, beautiful homes, mostly of the Queen Anne style or Painted Ladies. It was a very enjoyable stroll.

From there we headed over to the Unity Temple down on Lake Street. The temple does not look like a church, but that was by design, Wright’s design. The guided tour there was also very worthwhile. Although it is not a traditional style, it looks like a wonderful space to worship in. The temple opened in 1909 and still serves the same Unitarian Universalist congregation today.

The Green Line brought us back to downtown Chicago. It was a little early for dinner, around 4 pm, but we decided to eat anyway. We walked into Miller’s Pub on Wabash Avenue, as their sign had caught our eye the day before. Miller’s Pub opened in 1935 and was purchased by the Gallios brothers in 1950. The restaurant is still run by the Gallios family today.

We both ordered the BBQ ribs, since Miller’s is known for them. Keith had his half rack with shrimp, a salad, and fries. Ann ordered her half rack with a salad and spanakopita (spinach pie). She could tell from the other items on the menu that came with spanakopita that it was a popular side item. She was not disappointed. It turns out that the Gallios brothers are of Greek descent. The ribs were pretty tasty as well. We were both too full to order dessert.

A thunderstorm was brewing outside. We managed to hop on the Green Line before the rain really started, but we had to walk in it the two blocks from the train stop back to the hotel. We spent most of the rest of the evening in our room, watching the downpour out our window.

The rain eventually stopped and it looked like the skies might clear. It was the Fourth of July and the Navy Pier was still scheduled to set off fireworks at 10 pm. We didn’t want to head back downtown and fight the crowds of people, so we walked over to the lakefront from our hotel, hoping we could see the fireworks from there. We thought about trying to view them from the rooftop bar of the hotel, but we noted earlier that a couple of skyscrapers might be in the way.

We stood on the terrace on the east side of the McCormick Place Lakeside Center. There was one person already standing there when we arrived. We watched the steady stream of boats coming in and out of the harbor below us. By the time 10 pm rolled around, about a dozen or so other people had joined us.

Unfortunately, while we were standing there waiting, the fog, which had never quite completely cleared, just kept getting progressively thicker. By the time the fireworks started, we couldn’t see anything. We could faintly hear them, so we know they were setting them off. We were starting to regret not venturing down to Navy Pier, but then someone got a report from people at Navy Pier who said they couldn’t see the fireworks either. It does seem rather a waste that they would spend all that money on fireworks and set them off when no one could see them. Keith said he could visualize them in his mind and they were wonderful.

Sunday did not go according to plan. Initially, we took a couple of L trains over to Douglass Park. We switched from the Green Line to the Pink Line at the Ashland station. Then we got off at the California station, at the southeast corner of the park. That part went smoothly.

Ann had read that there were some Route 66 murals in Douglass Park. Route 66 passes right through the middle of the park. We walked around most of the park, but couldn’t find the murals. The information on the internet was that the murals were on the maintenance building. About the only buildings in the park are the Recreation Building and the North Lawndale High School along with Flower Hall, an entry way by the garden. We even asked the staff at the pool by the Recreation Building, but no one was aware of the murals. On the bright side, the park was a lovely place to go for a stroll.

Flower Hall looked like a Frank Lloyd Wright structure, but it was designed either by Jens Jensen, the General Superintendent and Chief Landscape Architect for the entire West Park System, or a friend of his. Jensen was familiar with the Prairie style that Wright was developing during the same time period, in the early 1900’s.

From Douglass Park, we walked over to two Route 66 landmarks, Lu Lu’s Hot Dogs and Ferrara Bakery, which were east of Douglass Park along Route 66. We knew Ferrara Bakery would be closed, but we had conflicting information on whether Lu Lu’s Hot Dogs would be open. We were hoping to get a Chicago Dog there for lunch. No such luck. It was closed. We took a few pictures, then continued walking to the Polk station for the Pink Line.

After we entered the station and went up to the platform, we learned that the train was delayed. It was going to be another 17 minutes or so before it arrived. We were getting hungry and had decided to go to Portillo’s on the corner of Canal and Taylor, where we knew we could get a great Chicago Dog. We wanted to take the Pink Line to the Quincy stop, but then Portillo’s was about a 22 minute walk from there. Or we could just walk from the Polk station, a 38 minute walk, which would get us there sooner. So we left the Polk station and walked.

Lu Lu’s and the Polk station are in what is called the Illinois Medical District, which contains several medical centers along with some universities, like the Rush University and parts of UIC (University of Illinois Chicago), such as their Retzky College of Pharmacy. As we were walking by a peaceful looking sunken courtyard with a fountain. Ann stopped to take a picture. A person on a bicycle saw her taking the picture and stopped to chat with us. He was excited to let us know what we were looking at was the Atkins Medicinal Plants Garden, filled with native plants that are used for medicines. Each plant has a little plaque explaining its use. Occasionally, there are guided tours of the garden. We noticed that he was wearing a pager and an employee badge on a lanyard around his neck. We’re assuming he was either a professor or a physician. We thanked him for the info, but didn’t go into the garden to check it out. We were too hungry.

We made our way over to Taylor Street, then it was a straight shot over to Portillo’s, right through the main drag of the area known as Little Italy. Taylor Street was lined with cute little shops and restaurants. Mario’s Italian Lemonade was doing a good business. Also along the street is the National Public Housing Museum.

Finally, we reached Portillo’s. We both had Chicago Dogs with fries. Yes, Portillo’s dogs are much better than the Chicago dog Keith had at Navy Pier a couple of days earlier.

After satisfying our hunger, we debated about what to do next. We could go up to the top of Willis Tower, but it was still foggy and we wouldn’t get any views. There was also the historic Dearborn train station, but that required more walking. So we decided to just walk over to the Roosevelt station and pick up the Green Line back to the hotel. We had gotten our fill of walking and decided to call it a day.

For dinner, we were just as lazy. We went up to the roof top bar of the hotel, the Vu. Their menu is a little upscale. Ann had the skirt steak with broccolini while Keith ordered the salmon with marbled potatoes. The food was delicious. Everything had some interesting seasonings. The potatoes came with a light green dipping sauce. We couldn’t quite figure out the combination of flavors, but we believe it was sour cream based. We were both too full to order dessert, quite a change from being so hungry earlier that day.

We’re normally not big city people, but we had a wonderful stay in Chicago. However, we were ready to start Route 66 and explore the little towns along the way.

Check out our related video: Chicago, Illinois

(Ann)