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Historic Route 66 Begin Sign

3.9 (9 reviews)

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On the corner of Adams & Michigan Ave. across the street from the Art institute of Chicago.
Tony H.

A cool little sight to see while passing around through downtown Chicago. The sign is on Michigan Ave & Adams St. right across the street from the Art Institute of Chicago. Being from LA where the end of Route 66 sign is out on the pier in Santa Monica it was pretty cool to see the beginning of the trail.

Sign
Steve A.

Curious to see where the famous road begins? If you like Route 66 stuff, this is a must visit for sure, but you won't be staying for long. There isn't much to it, so it's not that interesting though. Even though it's a significant place, it should only take a few moments to look at. Pretty much it's more interesting to read about it than it actually see it seems. Basically the history of Route 66 is more interesting than looking at this road sign in the middle of busy Chicago. It's located on Adams just west of Michigan. This is closest to the Adams and Wabash station. Certainly no one comes here just to see it. This is close to a few museums. Among these is the Art Institute. There's also a few restaurants such as the Berghoff among others. Check it out when you're seeing somewhere else around here. It only takes a few seconds to get a look at it and then you move on. This is close to a Loop station and many forms of public transportation.

San Diego 66 sign

Travelled backwards from San Diego to Chicago on Route 66. Come On Chicago, have some pride in your history. The dichotomy between the cleanliness of the sign and around the sign between San Diego and Chicago is amazing.

Ariel W.

Route 66 is so famous, it even inspired a song. "It winds from Chicago to LA More than two thousand miles all the way. Get your kicks on Route sixty six." When I was in Chicago I wanted to find the start to this historic road and it turns out it is right across the street from the Chicago Art Institute. In 1926, the U.S. federal highway system designated the number 66 to the route that ran from Chicago to Santa Monica. It was created in response to the rise in popularity of cars and the demand for safer and more direct roadways. Route 66 was made up of a series of pre-existing roads that followed the ancient trails made by the first people to reach North America 15,000 years ago. Indians used these foot trails and later they were traveled by fur trappers in the 1700's and pioneers in the 1800's. The roads were designated Route 66 so that it had consistent signs as it crossed state boundaries. By 1938, the road was fully paved. Route 66 travels over 2,400 miles, crossing 8 states, before ending at the Pacific Coast in Santa Monica, California. It runs through Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, and California. From 1926 to 1985, it was the most traveled route between the Midwest and the West In John Steinbeck's book The Grapes of Wrath, he referred to Route 66 as "the mother road, the road of flight" for those trying to escape the Dust Bowl and the Great Depression in the 1930's as they headed to California for a better life. WWII veterans used the route to hitchhike after they returned from war. In the 1950's and 60's, it was the route vacationing families in the Midwest took to the Grand Canyon and Disneyland. during this time a host of restaurants, motels, diners, gas stations, car repair shops, and tourist attractions popped up along the route. As the current federal interstate system was created to get people from point A to point B more quickly, many of the small towns on Route 66 were bypassed causing their death. Think Radiator Springs in the Disney movie Cars which was once a popular stop along U.S. Route 66 until it was bypassed with the construction of Interstate 40 and forgotten. Route 66 was decommissioned in 1985 and it is no longer officially designated or signed as Route 66 but if you have a Route 66 guidebook you can still travel 80 percent of this road today. Tourism and preservation groups along with its portrayal in movies like Cars, has renewed interest in the historic road. The 66 Corridor Preservation Program was created by an act of Congress in 1999 and it is administered by the National Parks Service. I hope to make the full Route 66 trip someday. Anyone want to come along? LOL. You can still visit many of the same tourists spots people visited in the 1950's. Other area are now ghost towns. "Won't you get hip to this timely tip. When you make that California trip. Get your kicks on Route sixty six."

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Skydeck - NEVER FORGET (look closely)

Skydeck

3.5(959 reviews)
0.6 mi•The Loop

#Chicago #flyforfun #friends #yelpfriends…read more So, we did all the touristy things and the Skydeck was one of stops. Located in the Willis Tower (formerly Sear Tower) you will find Skydeck. Take the escalator DOWN a few levels to get to the ticket agent. Here is my tip: Pay an extra $20 for the Expedited Line. Why? You won't be wasting your time, standing in line to take the elevator up 100+ floors. (the wait can turn into many minutes if not an hour...) Couple that with your wait when you get up the 100+ floors. The line you wait in for your photo op is an Expedited Line as well. You are given 2 minutes to take your pictures. With an Expedited Line Ticket you can return to the entry line and go back in for more pics.... A once in a life time journey for me but what a fantastic panoramic view from north to the south to the east and then to the west. A fantastic way to view Chicago and get your bearings for the rest of your visit. When you get back down to ground level; there are eateries in the Willis located on the street level.

Skydeck Chicago was amazing! I went for my scheduled 2 PM visit and was actually surprised that it…read morewasn't too crazy busy. Once you check in, you go through a museum-like walkthrough that covers Chicago's history as well as the history of the Sears/Willis Tower. There are also plenty of opportunities to stop and take pictures along the way. Once you reach the end of the walkthrough, you head up 103 floors to the Skydeck. As soon as I walked in, I was honestly blown away. Even though the building was once the tallest in the world, it's still such an incredible experience to see the entire city of Chicago from that high up. The skyline is absolutely breathtaking, and you can even see Lake Michigan from the top. It also wasn't too crowded when I went, which made the experience even better. I was able to do the Ledge as well, where you can step out onto the glass and take pictures and videos. You get up to 90 seconds when it's your turn, and you can get back in line if you want to go again. Everything was exactly as described, and I'm so glad I got to visit again for the second time as an adult. I also got my ticket through CityPASS Chicago, and the whole process was super smooth with no hiccups. Definitely one of the highlights of my Chicago trip and a place I'd recommend checking out, especially if it's your first time in the city!

Photos
Skydeck - Use your phone flash!

Use your phone flash!

Skydeck - Read sign if it's not obvious.

Read sign if it's not obvious.

Skydeck - Our friend living his best life

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Our friend living his best life

Chicago Riverwalk - PS. Chicago I love you.

Chicago Riverwalk

4.6(272 reviews)
0.5 mi•The Loop

The Chicago Riverwalk was one of our favorite things to do in Chicago. It was also very convenient…read moreto reach from our hotel because we were on the Loop and our room faced the Riverwalk. We got some great photos! Be sure to put this fabulous and popular activity on your List of Things to Do. There are many wonderful restaurants, bars, shops, great architecture buildings, great views, as well as the river cruise boats to see as you walk along. There are benches along the way as well as people sitting stairs to rest. It is about a mile + to walk. The Chicago Riverwalk starts at Lake Michigan (near Lake Shore Drive) on the east and ends at Lake Street on the west. It takes between 20 to 30 minutes to walk it without any stopping.

The Chicago Riverwalk is a beautiful place to walk along the river, and it would be easy to spend a…read morefew hours stopping for tapas snacks and bar hopping from one place to the next. We visited around 1:00 p.m. on a Saturday, and it was already becoming very crowded. The walkway was easy to navigate, but the number of people made it feel much less peaceful. Even the river itself was busy with tour boats and other traffic. We stopped at The Northman but skipped trying anywhere else because of the crowds. I would visit earlier in the day or on a weekday for a more relaxed experience. After seeing how busy it was, I also decided I would rather rent a boat and cruise along the river than fight the weekend crowds on foot. The Riverwalk is worth experiencing, but your timing will significantly affect how much you enjoy it.

Photos
Chicago Riverwalk - 07.04.25 view of the Chicago River and the RiverWalk from Michigan Avenue Bridge

07.04.25 view of the Chicago River and the RiverWalk from Michigan Avenue Bridge

Chicago Riverwalk - Rainy day today

Rainy day today

Chicago Riverwalk - Wrigley and Tribune buildings.

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Wrigley and Tribune buildings.

Landmark Theatres - Inside theatre 5

Landmark Theatres

3.4(27 reviews)
17.7 mi

Can you turn the freaking air on? Maybe at least the fan to circulate air. If you want to watch a…read moremovie in great seats but hot stuffy air and warm and musty this is your place. I get times are tough but it makes for a miserable experience

When we were looking for a local cinema to see Ne Zha 2 for the second time, this time with English…read moredubbing, we were happy to find Landmark at the Glen! It replaced Arclight which was in a decline. The cinema had been renovated 2 years ago. It was a Thursday afternoon, and the cinema was pretty quiet. There were big kiosks for ticket purchases, and the process was quick and easy. We got a small bag (which was not too small) for $10 plus tax, a little pricy for popcorn, but it was good. The popcorn guy was friendly, and he also doubled as the guy to collect our ticket stubs, and informed us which cinema room to go to. We were there for the preview of the movie, and we got the entire cinema #5 to the 3 of us! While the lobby and hallways of the cinema was nice and cool, this room was a little too warm. We totally understood that they would not cool down an entire room when there was no audience inside. I went to talk to the popcorn guy about the air temperature issue, and he promised to have it adjusted. As I went back to the cinema room. We could feel that cool air started to come out, and it was comfortable for the rest of the showing. The chairs were big, clean, and comfortable. Sound and picture were great. The movie itself was enjoyable just like the first time, and the English dubbing was perfect. The entire cinema was very clean. I was especially pleased with their restrooms being spotless clean. There is a bar in the lobby, and across from it was the biggest poster I've ever seen in a cinema lobby, it was a colorful digital poster of Ne Zha 2, very appropriate for such a spectacular movie. When we left the cinema after seeing the movie, there was another guy at the hallway collecting ticket stubs, and there was obviously more audience coming in. We enjoyed this cinema experience very much, and would definitely return to see other movies in the future.

Photos
Landmark Theatres - Kiosks in the lobby

Kiosks in the lobby

Landmark Theatres - Inside theatre 5

Inside theatre 5

Landmark Theatres - Front doors

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Front doors

Willis Tower - Entrance

Willis Tower

3.8(1.5k reviews)
0.6 mi•The Loop

What used to be known as the Sears Tower is now the Willis Tower. It used to be the tallest…read morebuilding in Chicago but I don't think that is the case today. The Willis Tower houses the Elevator of Skydeck The Willis Tower has a bunch of eateries on the street level The Willis Tower is a place you MUST visit if you're touring Chicago Not much more I can say that others haven't already brought to the forefront. An easy $100 in today's dollar.... food and touring all in

We visited Willis Tower during our December trip to Chicago…read more We didn't book the ticket in advance because it was cloudy the day before. When we arrived in the morning, the cashier told us that we should wait in the afternoon and hopefully, the sky cleared up. So, we bought the 2pm tickets. Luckily, the fog was gone by 2 pm and the sky cleared up. There were lots of photo props before we entered the elevator. Once we were at the top, there were several spots to experience the Ledge but we had to line up. The line looked long but it moved relatively quick because each family was only given 90 seconds to take pictures on there. Yeah, it was way too little time but you can actually rejoin the line if you're still want to take more picture. Overall, it was a very cool experience to be standing on the glass floor on Ledge!

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Willis Tower
Willis Tower - Chamber music in the sky

Chamber music in the sky

Willis Tower - I was too afraid to step all the was back to the outer wall. Others were posing and having a blast. I'd do it again!

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I was too afraid to step all the was back to the outer wall. Others were posing and having a blast. I'd do it again!

Cloud Gate - Cloud Gate ("The Bean")

Cloud Gate

4.6(1k reviews)
0.3 mi•The Loop

It is "The Bean"? "Cloud Gate"? "Millennium Park", "Grainger Park"? Sheesh!…read more It doesn't matter what you call it, everyone will know and it is a place to go at least once when you're visiting Chicago. The locals visit this place as a picnic area; take the family, enjoy the view, enjoy the crowd, etc. The visitors go there because you have to go there at least once when you're in Chicago proper. Easy train and bus access. OK, here is the story- CLOUD GATE is the official name of this sculpture, nicknamed THE BEAN, and it is located in MILLENNIUM PARK, adjoining GRAINGER PARK.... so there! Go See! Go Enjoy! By the way, they have local eateries and fast food places there too; including a vendor who serves the infamous CHICAGO DOG So- Go there or be square!

Millennium Park and Cloud Gate are absolutely worth visiting on a first trip to Chicago. Cloud Gate…read moreis essentially a really big, reflective bean. We visited late in the afternoon, and it was extremely crowded. We still managed to get good pictures, but we accepted that plenty of strangers would be featured in them. Go early if you want a quieter experience or photos with fewer surprise guest stars. We also walked through the park and saw Crown Fountain, with the large faces displayed on the screens. The park was clean, easy to navigate, and enjoyable to walk through. Cloud Gate may be crowded and slightly absurd, but it is iconic Chicago. You have to see the giant Bean at least once.

Photos
Cloud Gate - 07.04.25 touched the surface of The Bean... check!

07.04.25 touched the surface of The Bean... check!

Cloud Gate - 07.04.25 The Bean with Chicago's skyscrapers in the background and the clouds floating above

07.04.25 The Bean with Chicago's skyscrapers in the background and the clouds floating above

Cloud Gate - My wife, her parents, and me at the Bean.

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My wife, her parents, and me at the Bean.

Historic Route 66 Begin Sign - landmarks - Updated October 2026

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