This post is part of a series I’ve done on Route 66. In 2022, I drove the entirety of Route 66 from Chicago to Los Angeles. 2500 miles, 8 states, countless stories, and an endless stretch of small towns, neon, diners, motels, and roadside attractions. Read through all of my Route 66 posts here. They’re also linked at the end of this post. If you’re planning your own Route 66 road trip, either the whole thing or just a part, I hope these help you out. Enjoy the drive!
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, taking you all the way across the country, through states that a lot of Americans will never even see, before depositing you in sunny, glittery California.
As the Eastern anchor of Route 66 and the route’s official starting point, it’s been the launching point of countless road trips as most people choose to drive Route 66 from east to west.
Often called “America’s Main Street,” the very idea of Route 66 is kind of anti “big city.” Dreams of the journey tend to focus on wacky roadside attractions, vintage hotels, small mom and pop diners, long stretches of uninterrupted road, and sprawling vistas, yet Route 66 is bookended by two of the country’s largest cities.
And folks, Chicago is something to see. Take it from someone who has been around the world, but didn’t make it to this sprawling city that’s within driving distance from where I live until my big Route 66 trip.
If you like big cities (hey, they have their perks), then you’ll feel right at home in Chicago with its towering skyscrapers, world class museums, public transportation, walkability, and expansive food scene.
And if you don’t generally like big cities…I think there’s still something to like about Chicago. Honestly, it’s one of the coziest feeling big cities I’ve ever been to. It feels compact for all of its offerings and while NYC often feels jarring to the senses, Chicago isn’t quite plagued by big city problems to the same degree. At least the downtown area.
It’s easy to get around, most of the tourist attractions are clustered in a walkable part of downtown, it’s relatively clean (I swear they’ve got to have an army of people scrubbing the streets and watering plants-I’ve never seen a city that was landscaped as well!), and while it’s a world class city, it feels so…midwestern.
So whether you’re embarking on a huge transcontinental road trip or just looking for a few Route 66 related things to see and do around Chicago, I’ve rounded up the best Route 66 stops in Chicago and its surrounding suburbs…Chicagoland.
From downtown Chicago to Joliet (Chicago’s last big suburb), it’s 40ish miles of Route 66 and while there’s a surprising lack of Route 66 related sites left in the area, there are some pretty good ones.
Route 66 in Chicago
Ready? Let’s get those kicks!
First things first, I know a lot of Route 66 “purists” are trying to retrace the entire route foot by foot and hey, great for you, BUT I seriously recommend doing downtown Chicago on foot. Most of the streets are one way and parking is a pain so I think you’ll be much happier getting a hotel room downtown, paying to park the car, and just exploring the area for a couple days.
Historic Route 66 Begin Sign
If you’re only going to stop and see one Route 66 related site within 50 miles of Chicago, this has got to be it right?
The start of every journey needs to be documented with a picture, and this is the spot.
There are actually two signs and they both sit on either side of Adams St right off Michigan Ave (directly across the street from the Chicago Art Institute).
The one on the south side is the easiest to take your picture with. It’s lower and it’s also usually covered with stickers (I’m amused by how angry this makes people in a few Route 66 Facebooks groups I’m in…I wonder if they’re also bothered by the graffiti at Cadillac Ranch ; )
The sign on the north side of the street is mounted up higher (so it’s harder to get a picture with it but it’s sticker free).
You won’t have to look too hard, there’s usually a crowd trying to get photos with the signs.
Family owned and operated for over a century, the Berghoff has been serving traditional German food since 1898. They were also Chicago’s first liquor license granted after prohibition ended. They’re closed Sunday and Monday (of course when I was there), so I didn’t get to try it, but they’re open for lunch and dinner (I gather there’s a more casual cafe and a more formal restaurant all in the same building). The location is really convenient to a lot of downtown attractions.
This famous diner has been serving breakfast and dinner to hungry Chicago patrons and Route 66 travelers since 1923. I twisted around my travel plans pretty good to hit up Lou Mitchell’s (closed Monday and Tuesday), but honestly…So far, this has been one of my more disappointing experiences on Route 66. Which is a shame because everything about it seems like something I would like.
Hopefully I just caught them on a bad day, but after reading some recent reviews (plus one of the managers kind of made a speech to the whole restaurant about us being patient with them since they’re short staffed/COVID wiped them out, etc.) it may be a somewhat often occurrence and it seems like they know their experience isn’t what it used to be.
Here’s what you should expect: 1) Good food! Really, none of my complaints had much to do with the food. It’s solid diner/breakfast food but I would say elevated (it doesn’t have that greasy spoon vibe, but definitely hearty). 2) A line – especially on weekends. I had read about this and honestly I consider a line out the door for a breakfast place during prime hours on the weekend a positive sign. We showed up about 10:30ish on a Sunday and the line was pretty long, but we were seated within 20 minutes or so. Perfectly fine. 3) High prices for a diner. Breakfast for 2 was $55 with tip. Honestly, for a place with a prime time location in downtown Chicago that’s cute with history and good food, I can justify the premium. BUT everything needs to be spot on. And it just wasn’t.
Experience seemed to vary wildly here depending on your server, and ours was…stressed, stretched thin, frazzled, slow to bring things (condiments, sides of toast, drink refills, silverware, etc.) and honestly a little rude (especially to people at a table next to us).
This place is known for handing out boxes of milk duds to women and children (I think they were out and I didn’t even ask about it), but I did ask about the donut holes and he said they ran out of them but he would bring some pieces of whole donuts (they never came), but we noticed that other servers were bringing them out to their tables after that.
Nothing scathing, but half a dozen little things like that (getting upcharge like $8 for a large glass of orange juice, etc.) plus the manager’s speech about everyone being patient and it left me with the impression that they’re getting feedback that customers aren’t happy and are maaaaaybe using COVID recovery as an excuse to pack people into the restaurant, charge a premium, and under deliver on experience. It honestly didn’t even seem like they were short staffed, it just seemed like the place was packed too full with extra tables and the space wasn’t designed to accommodate that many people.
ANYWAY. I did not have a great experience, but I felt like I really wanted to have a great experience and wouldn’t totally write this place off (it’s a Route 66 Chicago institution). Hopefully they get their quality issues sorted out soon and I really do think this is a case of bad timing (my personal experience plus COVID recovery in general) because a place like this wouldn’t stick around for a HUNDRED years if the norm was what I experienced.
So for now, if you give it a try, just be prepared for an above average breakfast price and the potential for hit or miss service. Lower expectations always yield better results ; )
Also, on a location note…it’s on Jackson between Jefferson and Clinton and it’s pretty close to Union Station and the Willis Tower (formerly Sears Tower) if you’re in the area for either of those things.
Ogden Ave Leaving Downtown towards the Suburbs
Ogden Ave runs for miles (and miles) from downtown Chicago out through the city. We actually drove into Chicago on Route 66 (eastbound) and I was loosely trying to stick to Route 66 without being too precious about it, and we ended up on Ogden Ave at some point as the skyscrapers appeared in the distance. I remember saying “I don’t know what road this is but it looks like it goes straight downtown” and well, it pretty much does. It was neat driving 10-15 miles of it and just getting closer and closer until boom we were right in the middle of the city.
So anyways, I’m sure it’s more dramatic driving INTO Chicago on Ogden instead of out, but it’s a pretty long distance stretch of Route 66.
The Chicago Suburbs
Leaving Chicago “proper,” Route 66 meanders through what still seems like it’s still the city even though at some point probably changes from different neighborhoods to different towns.
It’s all still Chicagoland at this point. Route 66 spots are still kind of sparse, but I’ve included a couple here (plus the towns/areas they’re in so you can track them on a map).
Cindy Lyn Motel: Cicero, IL
I hadn’t seen or read anything about this place before I spotted it and it seems like a decent place, although I’m not sure about the location. I think I’d want to be either actually in the city (downtown) or farther out in a suburb (like Joliet).
Henry’s Drive-In: Cicero, IL
You’ve got to try at least one Chicago style hot dog, and this seems like the perfect place. It’s a classic Route 66 spot…look at that neon!
Dell Rhea Chicken Basket: Willowbrook, IL
Serving fried chicken dinners since 1946, it’s a very cute place (such an iconic sign!), but it’s in a super weird location. It fronts I-55, and you have to go through a new(er) built shopping complex (Target, Starbucks, La Quinta, Denny’s, CVS, etc.) to get to it so it’s not on a quaint stretch of Route 66, but once you get back there, it’s CUTE. I wasn’t passing through at the right time to stop on this trip, but planning to hit it another time because it looks like the kind of place I would like.
White Fence Farm: Romeoville, IL
Another famous fried chicken place that’s been open on Route 66 since 1954. It’s now a small chain across the Chicago area.
Joliet is considered one of the last big Chicago suburbs and it’s also one of the first sizeable cities/towns that you’ll come to that feels distinct from Chicago.
For that reason, if you’re wanting to bypass Chicago on your Route 66 trip (hey, some people are big city adverse or they’ve been to Chicago before and want to spend their travel time out along the route) Joliet makes a good alternative starting point.
There’s a fair bit to see and do in Joliet.
Opened in 1926 as a grand movie palace (but now home to mostly theater/musicals, concerts, etc), I knew the Rialto was something to see, but I was still impressed when I pulled up. Yes, the neon sign is amazing, but the architecture of the building is super ornate. I’d love to see the inside next time.
Joliet Route 66 Welcome Center
Housed in the Joliet Area Historical Museum, this is the first official Route 66 welcome/visitor center you’ll find along Route 66. Sadly, it wasn’t open yet when I drove through Joliet, but it looks really nice.
Rich & Creamy
You’ve gotta love a good old fashioned ice cream stand plus this one has the Blues Brothers on top. It’s located next to “Route 66 Park,” but check your expectations because it’s mostly just a parking lot. There are some historical plaques and signs, but when I was there they were too torn and sunbleached to read.
Old Joliet Prison
Built in 1858 and in operation until 2002, this is the prison that was featured in the movie Blues Brothers. And since it’s been decommissioned, it’s now OPEN TO TOURS. I don’t know why, but this seems wild to me. There can’t be too many places in the US where you can tour a prison like this. So it’s a pretty big thing to do. I passed on it, because honestly it creeped me out, but my impression is that it’s a quality attraction. They have a spectrum of tours available from self guided tours to the main tour to an after dark tour to one led by former prison guards.
Things to Do in Chicago BEFORE Your Route 66 Trip
Well that covers the first official 50 or so miles of Route 66 and as you’ll see once you get further down the road, the Chicago area is pretty light on Route 66 spots and sites, BUT as one of the US’s major cities, there is sooooo much to see and do here.
Unlike some of the other big cities along Route 66 (St Louis, Oklahoma City, Albuquerque, or even LA where it ends), I was surprised that Chicago didn’t have more Route 66 sites and spots to see. But it’s a great city with a lot to experience, so if you’ve never been before (I hadn’t before this trip) Chicago is definitely worth a few days before you get going on Route 66.
I’ve rounded up a few top notch attractions and things that are “just so Chicago” to check out:
Art Institute of Chicago: Sitting right at the starting point of Route 66 at the intersection of Michigan Ave and Adams St, you can almost claim this one as a Route 66 attraction. The museum is HUGE (you could easily spend most of the day here), and while the art collection is extensive and spans so many time periods and regions, I think their impressionist collection is pretty impressive so if you’re short on time, that’s where I’d start. You also don’t want to miss Cloud Gate (the Bean).
Field Museum: Chicago’s natural history museum is one of the largest in the world.
Shedd Aquarium: The Shedd Aquarium and the Field House are next to each other so it would be easy to visit both at the same time.
Cubs Game at Wrigley Field: Whether the Cubbies are your team or not, going to a game at Wrigley Field is a Chicago (and a baseball) institution. Tickets are surprisingly inexpensive (usually start around $25-30, I got tickets behind home plate for about $55) and if the Cubs aren’t at home (or it’s the offseason) you could also consider a tour of Wrigley Field. And if you’re interested in a tour, just be aware that on days the Cubs are playing the tour is much less extensive than on days when they’re not.
Architecture River Cruise: This is the #1 thing to do in Chicago for a reason. Tours last about two hours (there are so many companies, but I like the one from the Chicago Architecture Center) and besides being a great way to learn about the history of Chicago and it’s fabulous architecture (it’s the city that invented the skyscraper), it’s just a super pleasant way to spend some time.
Willis Tower: Once the Sears Tower, always the Sears Tower and for a while it was the tallest building in the world. So if you want to recreate your own Ferris Bueller scene, head on up to the 103rd floor and see if you’re brave enough to step out onto the Ledge (I wasn’t ; )
Eat Deep Dish Pizza: The debate about the best deep dish pizza in Chicago is about as fierce as the debate between New York and Chicago style. For the record, I’m a New York style kind of girl, but when in Rome…
Like I said, everybody has their favorite, but I went with Lou Malnati’s (a longtime local place that’s now a Chicago area chain).
If you want to put together the perfect day in Chicago, check out this Ferris Bueller’s Day Off post I put together that’s a pretty epic 1 day itinerary.
Planning a Route 66 road trip? I’ve got all of the info you need!
I’ve written about my cross country road trip pretty extensively section by section. Read them all here: Part 1 (Chicago), Part 2 (Chicago to St. Louis), Part 3 (St. Louis), Part 4 (St. Louis to Springfield MO), Part 5 (Springfield, MO), Part 6 (Springfield, MO to Tulsa), Part 7 (Tulsa), Part 8 (Tulsa to OKC), Part 9 (OKC), Part 10 (OKC to Amarillo), Part 11 (Amarillo), Part 12 (Amarillo to Albuquerque), Part 13 (Albuquerque), Part 14 (Albuquerque to Flagstaff), Part 15 (Flagstaff), Part 16 (Flagstaff to San Bernardino), Part 17 (Los Angeles).
I’ve got the scoop on where to stay including the best Route 66 motels recommendations.
And finally, my final trip recap where I spill the beans on how many days you need, the best itinerary, my favorite don’t miss spots, and other tips.