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    Historic Route 66 Begin Sign

    3.9 (9 reviews)

    Historic Route 66 Begin Sign Photos

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    Sanjay G.

    You'll find the 'Begin Route 66 sign' on E. Adams Street just west of where it intersects with Michigan Avenue, directly in front of the Art Institute of Chicago. it's been the launching point of countless road trips as most people choose to drive Route 66 from east to west. Route 66 in Chicago feels like the start of an awfully big adventure. 2,500 miles of the Mother Road sprawling out in front of you, now as part of my bucket list- I need to go to Santa Monica Pier, take a picture with the " Route 66 ends here sign" and merge both. hahaha...

    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.

    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.

    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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    The Rookery Building - FLW iron installation.

    The Rookery Building

    4.5(75 reviews)
    0.4 miThe Loop

    Visiting The Rookery was one of those quiet Chicago moments that really sticks with you. From the…read moreoutside it's understated, but once you step into the Light Court, the space opens up with natural light, ironwork, and detail everywhere you look. The Frank Lloyd Wright staircase is subtle but impressive--nothing flashy, just solid design that holds up over time.Tip for first-time visitors: go on a weekday and aim for mid-morning if you can--the light is best, it's calmer, and you'll actually have space to stop and look around. It's not a long visit, but it doesn't need to be. The Rookery is simple, beautiful, and worth slowing down for.

    Make no mistake, this space is stunning and definitely something to see. As a recent wedding guest,…read moreI was expecting more. The setup of the building makes for a cramped wedding. We had to stay in the crowded lobby for a long time before the ceremony space was opened. The restrooms are far away from the action, about as far from the party as they could be. The second floor cocktail space was cramped. The two bartenders were soooo slow. Not sure if they were part of the catering staff the Rookery uses or separate. Dinner was exceptional. No one knew the bar moved from the second floor to a space under a first-floor staircase for drinks after dinner. There was no announcement of where desserts were located. A lot of the issues I had with the wedding could have been eliminated had an experienced planner been hired. Too often during the day guests were not sure where to go or what was happening, what was next. It's a beautiful space but my advice to couples would be to hire a planner who is experienced and who has worked several wedding at the Rookery. Also, I was told the space was rented the night before the wedding so the couple couldn't have a rehearsal. Unfortunately, that was obvious and added to the disjointed event. Also, some tourist walked into the back of the ceremony space during the wedding. I would have thought Rookery staff/security would keep tourists out of a private event, but this is one of those things that will become a funny wedding story in a couple of years.

    Photos
    The Rookery Building - Glass canopy

    Glass canopy

    The Rookery Building - FLW Planters

    FLW Planters

    The Rookery Building - Glass canopy

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    Glass canopy

    Skydeck Chicago - NEVER FORGET (look closely)

    Skydeck Chicago

    3.5(945 reviews)
    0.6 miThe Loop

    I have only been on the Skydeck once. I absolutely urge first-time visitors to check it out. The…read moreChicago skyline from the deck is breathtakingly beautiful. You'll need to purchase tickets to enter. The lines can sometimes be long but they do try and control that. Of course they have a gift shop...a few actually. You can pay for a photo of yourself on the deck and you can also snap some of your own. Staff are accommodating. You are able to learn a lot of history as well as seeing other important historical displays about the city. Big touristy thing to do? Yep! Should you do it? Yep!

    This is super touristy, but who cares, it's worth it! When in Chicago, this is a must do! We got…read morethe CityPass, which normally I would be bear-ish on something like that, but it was totally worth it. This is a pretty pricey single attraction for a family, but bundled with the 5 venue pass, this makes it much more reasonable. You also get the Expedited Entry included for free with your CityPass, which I would absolutely not pay the extra amount for (about $20 more per adult and $30 more per kid depending on the the day), but it made it super easy to get into the glass ledges. We went on a random Thursday, before most kids were out for the summer, and there was no wait to go up the elevator, and no wait for the expedited line for the ledges. They give you a set amount of time in the ledges, it seems like 90 seconds when it's busy and 2 mins 30 secs when it is slower, but you can get back in line and do it again. With the expedited pass we went 3 times into the ledges so that everyone could get all the photos they wanted. The rest of the view around the perimeter of the building was nice, and like I said when we went, not crowded, so we took our time and enjoyed the view. All told we probably spent an hour at the observation level. There is a gift shop up top, but everything they have up there, they also have in the lower level store (and more) when you exit the down elevator, so don't feel like you have to buy souvenirs up top. My boys chose a souvenir at the top and then had buyers remorse when they saw more for sale down below; thankfully they accepted returns and they were able to swap for the souvenirs they really wanted. All in all, this was worth the walk up Jackson from the Art Institute, and now I can say I have been in 3 buildings that when they were built were the tallest in the world!

    Photos
    Skydeck Chicago - Use your phone flash!

    Use your phone flash!

    Skydeck Chicago - Read sign if it's not obvious.

    Read sign if it's not obvious.

    Skydeck Chicago - 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(262 reviews)
    0.5 miThe Loop

    Very chill and relaxing. With much to see and get some nice steps in…read more Certainly recommend if you're looking to cut back on just spending money everywhere you go.

    One might expect me to be all doom and gloom about the sheer number of restaurants and bars along…read morethe river. Surprisingly, I won't be that guy, at least not this time. The main thing I really love about the Riverwalk is that it's a place in Chicago where someone can simply exist and vibe without the necessity of spending money. There is more than enough space to walk along the riverfront, take a seat, and enjoy the atmosphere. In terms of safety, there are more than enough "eyes on the street" as well as a visible police/private security presence. As with any high-traffic spot, use common sense, but other than a possible pickpocket, I don't foresee any issues. In terms of cleanliness, it is well-maintained, and I've not encountered any noticeable dirt, grime, or trash. I also really appreciate that the Riverwalk has both public bathrooms and is accessible! Accessibility needs no further explanation, and being able to wash up without buying an overpriced drink is worth its weight in gold. Another Yelper has compared it to the San Antonio River Walk and called out Chicago for having a shorter, less green "rip-off" of what one would find in Texas. However, I believe one should cast this comparison aside and judge the Chicago Riverwalk on its own merits. With that said... The final verdict: The Chicago Riverwalk is not your traditional, greenery-filled park. It is, however, a fantastic public space to take a stroll, have a bite, or just relax. Better still, while there is no shortage of tourists, it is an excellent destination for locals and visitors alike.

    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 - Wrigley and Tribune buildings.

    Wrigley and Tribune buildings.

    Chicago Riverwalk - Trump tower dominates the skyline looking west.

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    Trump tower dominates the skyline looking west.

    Landmark Theatres - Inside theatre 5

    Landmark Theatres

    3.7(24 reviews)
    17.7 mi

    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.

    This movie theater's really cute. I think it's a hidden gem in the Glen. Located right next to Yard…read moreHouse in Glenview, IL. The guy was very helpful getting me a cup for water and had the whold theater to myself. Definitely coming back.

    Photos
    Landmark Theatres - Kiosks in the lobby

    Kiosks in the lobby

    Landmark Theatres - Inside theatre 5

    Inside theatre 5

    Landmark Theatres - We held our ribbon-cutting with The Village of Glenview on Nov. 17, 2022.

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    We held our ribbon-cutting with The Village of Glenview on Nov. 17, 2022.

    Willis Tower - Entrance

    Willis Tower

    3.8(1.5k reviews)
    0.6 miThe Loop

    I will always call it the Sears Tower. I can't help it, that's what it was called the first time I…read moreever saw it and you know how it is...some of us humans just don't adapt to name changes of places we know and love. Anyway, I have been to Chicago many, many times (if you see me at a Yelp event, ask me why) and I like to see the tower whenever I am in the neighborhood. No longer the tallest building in the world, it is still a spectacular sight. The history and origin and the fact that it was the first skyscraper still holds intrigue and meaning for any architecture lover. As you can imagine, it can be extremely busy because after all, it is a building that holds businesses. However, that is not always the case. I have been at various times of day and it just really depends on the time, etc. If you are going for the first time, you absolutely want to get a view from the deck (Skydeck). The views are beyond incredible.

    I went to Willis Tower at 5 PM on a weekday with absolutely no idea what kind of crowd situation I…read morewas walking into. I had mentally prepared myself for lines, chaos, and the slow march of humanity. Imagine my surprise when I basically walked right in. In fact, my longest wait of the entire experience was for an elevator, which feels like a very reasonable thing to wait for in a giant skyscraper. I also loooooooved all of the historical information provided throughout the experience. It kept things interesting and made the journey feel like more than just walking in and riding an elevator to a great view. The cute photo ops sprinkled throughout were a nice touch too. And can we take a moment to appreciate the bathrooms? There were plenty of them and they were so clean. THANK YOU. As someone who judges attractions at least partially on restroom availability, this earned major points from me. Supreme appreciation. Everything felt organized, easy to navigate, and flowed really well. I don't know if I should credit the time of day, the weekday timing, or if it's always this smooth, but whatever the reason, I was pleasantly surprised from start to finish. Would absolutely visit again.

    Photos
    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!

    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!

    Willis Tower - Lots of fun photo ops while heading up to the tower.

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    Lots of fun photo ops while heading up to the tower.

    Cloud Gate - Cloud Gate ("The Bean")

    Cloud Gate

    4.6(988 reviews)
    0.3 miThe Loop

    Cloud Gate aka "The Bean" is one of the best spots in Chicago - . If you've just arrived in town,…read morethis is an easy and classic first stop in Millennium Park. The mirrored, bean shaped sculpture acts like a giant mirror, giving you a unique reflection of Chicago's skyline and the crowd around you. Obviously, it's a great place for photos and a must visit in Millennium Park.

    Cloud Gate, otherwise known as the Bean, sits in the middle of Millennium Park in downtown Chicago…read moreand is one of those public art installations that consistently surprises people who encounter it for the first time despite being one of the most photographed objects in the city. I walked up to a seamless polished stainless steel form that reflects everything around it without a single visible seam or joint across its entire surface. That engineering achievement alone is worth appreciating before I even started engaging with what the reflections actually do. The reflections are the experience. I watched the Chicago skyline curve and distort across the surface in a way that shifted constantly depending on where I was standing, and walking slowly around the perimeter gave me a different composition every few steps. Walking underneath the concave arch in the center, which locals call the omphalos, produced a funhouse mirror effect that reflected me and everyone else from overhead in a way that was consistently disorienting and engaging regardless of how many times I have seen it. On a clear day with blue sky the effect was particularly strong, with the skyline wrapping around the sculpture against a bright background. On overcast days the palette shifts toward silver and grey and produces its own version of the thing. Admission is free and the park is open and accessible, which made Cloud Gate an easy addition to my Chicago itinerary without any planning required. It gets crowded, particularly on weekends and during summer, and the area immediately around the sculpture fills with people taking photos throughout the day. Early morning visits before the crowds build give you a more relaxed experience and better light for photography. It is one of the few landmarks in any city that genuinely lives up to what people say about it.

    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.

    Buckingham Fountain - ComEd's Switch on Summer

    Buckingham Fountain

    4.5(413 reviews)
    0.4 miSouth Loop, The Loop

    Still five stars. It's running today and it's very crowded. Great to see so many people enjoying it!read more

    If you are vising Chicago, this is one of the not to be missed iconic landmarks. The Buckingham…read moreFountain is managed by the Chicago Park District is one of largest fountains in the world. It features impressive water displays and stunning architecture in the beautiful setting of Grant Park. The Buckingham Fountain was built at a cost of $750,00 and it was dedicated on August 12, 1927. Philanthropist Kate Buckingham donated the funds for the fountain as a tribute to her brother, Clarence who was an art collector of Japanese prints. Kate collected medieval sculpture, tapestries, and decorative arts. In addition to the Clarence Buckingham Memorial Fountain she also donated a statue honoring Alexander Hamilton in Lincoln Park and her family's art collection to the Art Institute of Chicago. Clarence Buckingham had been a governing member and a trustee of the Art Institute and Kate was influenced by his association with the institution. The Buckingham Fountain was designed by architect Edward H. Bennett in a classic Art Deco style out of pink marble. The sculptural elements were created by French artist Marcel Loyau. The fountain resembles a rococo style wedding cake and was inspired by the Bassin de Latone and modeled on the Latona Fountain at the Palace of Versailles in France. The fountain symbolizes the vastness of Lake Michigan, with four groups of bronze seahorses representing the four states bordering the lake: Wisconsin, Illinois, Indiana, and Michigan. The fountain is able to propel 14,000 gallons of water per minute. At night the fountain comes alive with lights and dancing water jets. The fountain is known for being featured in the opening of the television show, Married with Children. The Buckingham Fountain stands as a symbol of Kate Buckingham's philanthropic generosity and her love for her brother and the City of Chicago. Enjoy a picnic one one of the well maintained lawns and seating areas near the fountain where you are to create a lasting memory in the heart of Chicago. I will always treasure my visit.

    Photos
    Buckingham Fountain - Married with children fountain

    Married with children fountain

    Buckingham Fountain - IG: @ammysalamii

    IG: @ammysalamii

    Buckingham Fountain - IG: @ammysalamii

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    IG: @ammysalamii

    Historic Route 66 Begin Sign - landmarks - Updated June 2026

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