Route 66 Chicago: A Guide To The Start of Route 66 & 2 Days In Chicago!

Last Updated on August 22, 2022

Chicago is the start point of the 2446 mile road trip to Los Angeles that is otherwise known as Route 66!  I often see a lot of questions from people wondering the best places to stay, how to go about renting a car, where is the Route 66 start sign located, what to see in 2 days in Chicago? Hopefully I can answer some of those questions in this Route 66 Chicago guide!

Disclosure: This post contains affiliate and sponsored links. I may make a small commission on purchases made after clicking the link, at no extra cost to you. For more information visit my Privacy Policy.

Route 66 Chicago

The chances are if you are going to be driving Route 66 from Chicago, you’re likely to arrive in Illinois’ ‘Windy City’ via the airport, most probably Chicago O’Hare (ORD).  First things first is you have a couple of options on where to stay and exactly HOW MUCH you want to drive in Chicago?

Quick Links

Where to stay in Chicago/start your journey

Route 66 start sign – Where does Route 66 start in Chicago

Chicago Itinerary 2 Days

Landing in Chicago

Where To Stay in Chicago/Start Your Route 66 Journey

Here are a couple of my suggestions for how you could start your Route 66 journey or where to stay in Chicago:

Option 1 – Stay in a Chicago airport hotel

I’ve since been back to Chicago several times, but when we drove Route 66, this is what we opted to do.  There are several pros to staying near the airport.  Depending on your budget, there are cheap airport hotels ($50 a night – Motel 6). Or the larger ‘premium’ chains such as the Hilton and the Marriott ($120+). Most have free airport shuttles.  There are more options for hotels that also offer free parking.  All the large car rental companies are located at the airport.  The CTA train (blue line) goes directly from the airport to Downtown Chicago and takes around 50 minutes.

Chicago Airport Hotel

We arrived fairly late day 1 and got the free airport shuttle to the hotel.  Day 2, we got the free shuttle to the nearest CTA station and spent a day in Chicago, exploring on foot.  After our day in Chicago we took the train back to the airport to then pick up our rental car. This saved us the cost of 1 day’s rental as we collected it on day 2. Then we drove it straight to our airport hotel just down the road.  Day 3 we started driving Route 66 but used the GPS to get us to Joilet, one of the first towns on the Route which was mainly Interstate driving.

As international visitors that hadn’t driven in the USA before. This was more in our comfort zone while we got used to our car and American roads (and drivers)! I lived in the USA and I still don’t really like driving through Chicago.

🏨We stayed at the Comfort Suites O’Hare Airport in Schiller Park.  I have also stayed at the Motel 6 in Elk Grove Village.

Option 2 – Stay in Downtown Chicago WITHOUT a car

Similar to option 1. Ride the CTA train into Chicago and stay at a Downtown hotel rather than stay at the airport.  When you go to start Route 66, take the train back to the airport, collect your rental car and then begin the drive!

Chicago Downtown Chicago in a day

Staying Downtown will obviously put you closer to all the ‘action’.  There are plenty of restaurants, bars and attractions to keep you busy.  The CTA is pretty easy to use. There are both buses and trains and the ticket can be used on both.  It does mean carting all your luggage into the city though but plenty of people do it.

🏨I stayed at the Chicago Loop Hotel in Downtown. It’s right on Adams St, a few blocks away from the Route 66 start sign!  It’s on the lower budget end of hotels in Downtown Chicago but I really liked my stay.  They have free yoga mats in the rooms, refillable water bottle stations in the hallways and a British pub on the lower floor (which was so good I went there for dinner AND lunch the following day!).

Option 3 – Stay in Downtown Chicago WITH a car

🏨I have done this too, but stayed at the Chicago South Loop Hotel which is a little further south.  Parking in Downtown can be expensive and the Chicago South Loop Hotel is one of only a few that have free parking.  This hotel is around 3 miles from the begin sign (around a 15 minute drive along S Michigan Ave) if you really wanted to start the Route from the official start!  For sightseeing, I’d recommend using public transport or Uber, rather than driving around the city.

Route 66 Start Sign – Where Does Route 66 Start in Chicago

🗺78-98 E Adams St, Chicago, IL 60603, United States

So where does Route 66 start in Chicago? As mentioned, the Route 66 Begin Sign is located on the corner of E Adams St and S Michigan Ave, right opposite The Art Institute of Chicago. It is set slightly back from S Michigan Ave. After revisiting the Route 66 Start a couple of times, it was sad to see that the whole sign had almost been completely covered in stickers, you could barely see the bit that said ‘BEGIN’.  

I understand why people do stick their ‘groups’ sticker on it but it does slightly ruin it for other visitors. So I was glad to see a completely clean, shiny new sign.  I doubt it’ll stay blank for long though.

Chicago Route 66 Start

A block away from the start sign, on the corner of E Adams St and S Wabach Ave (just below the CTA line), there’s a very small park with an Illinois Route 66 sign in it.  This sign is covered in stickers, but doesn’t annoy me, I actually quite like the stickers being on this one.

Route 66 Chicago Illinois Sign

E Adams St have really embraced Route 66 in recent years, with the appearance of several more shiny new Route 66 signs dotted along this street.

The Route 66 End sign is a block south on E Jackson Blvd.  You might want to see this but then it may only appeal more to Eastbound travellers.

Driving The Route

Historic Route 66 follows Adams St and then cuts diagonally across Chicago on Ogden Ave.  Ogden Ave eventually reaches the I-55 which heads towards Joliet.  If driving from the airport you’ll most likely be on the I-294 which connects onto the I-55 at the same point close to where Ogden Ave joins it.  The Interstates do have tolls.  They accept an I-Pass or you have 7 days to pay the toll online at Illinois Tollway. Just make a note of the ‘Plaza’ number as you pass through it.

Chicago O’Hare has plenty of car rental options, you’ll find all the main chains.  However it’s worth keeping in mind that renting a car in Chicago and dropping it off in Los Angeles, you will encounter a one way drop off fee.  We rented a GPS too for city navigation and to get us back on track if we got lost, otherwise I highly recommend the EZ-66 Guide, this was a great resource with step by step driving instructions for the whole route.

Chicago Itinerary 2 Days

Embarking on a full journey across the USA, you may not have a huge amount of time in the city. But it’s good to at least have a night or 2, so you at least have a full day in Chicago.

Day 1 in Chicago

Willis Tower

🗺233 S Wacker Dr, Chicago, IL 60606, United States

As you can imagine, Adams St is a good place to start your journey as this is where you’ll find the Route 66 start sign.  Along the same street is the Willis Tower, with its observation deck on the 103rd floor and 4 glass blocks that stick out the side of the building.  ‘Sky Deck‘ gives visitors the chance to stand on a glass floor and look directly down 1365ft to the street below.  There is a 2nd observation tower in Chicago, the John Hancock tower, which is home to ‘Chicago 360’ and ‘Tilt’.  If you plan to visit, go early before the lines get too long, or purchase a ticket to skip the line in advance.

You can find out more about the differences between the two observation decks here: 360 Chicago vs Skydeck: A Guide To Chicago’s Observation Decks!

Millennium Park

🗺201 E Randolph St, Chicago, IL 60601, United States

Millennium Park (at the end of E Adams St) is a great free must see while in Chicago.  The Crown Fountain consists of giant 50ft glass brick towers that display short videos of the faces of Chicago locals.  The water feature part of the fountain operates between May and October, creating a paddling pool area.  A really fun part of the fountain is that every now and then the person in the video will move their mouth and water starts spouting out, soaking children that are eagerly waiting below!

Of course Millennium Park is also home to Cloud Gate…aka The Bean!  A giant reflective ‘blob’, with lots of people pulling faces at it.  I love how sometimes the smallest of things can bring a child like joy to adults!

For those looking for a cool shot, I’d stand right underneath and look up!  Cloud Gate was designed by the same architect, Anish Kapoor, that created the ArcelorMittal Orbit in London for the 2012 Olympics.

The BP Footbridge is another artistic/public art installation.  As well as being a cool funky snake like shape, it also acts as a traffic noise barrier!  I don’t think locals really appreciate it though, while I was taking a photo of it, I heard a guy behind me go “What’s she taking a picture of?  It’s just a bridge?”.  I’ve never had someone question my photography before!

The Jay Pritzker Pavilion is another Millennium Park icon.  This is a bandshell that’ll sometimes host free music events.

The Lurie Garden is nice on a summer’s afternoon.  There’s a little stream where loads of people sat with their feet in the water just reading books, having a snack or chilling in the sun!

Chicago Mini Golf
Maggie Daley Park

Maggie Daley Park is connected to Millennium Park by the BP Footbridge and is great if you have kids. There’s loads of playground equipment, a mini golf course, climbing walls and an ice skating ribbon (some activities include a fee).

Grant Park

Just south of Millennium park is Grant Park, every hour on the hour from 8am, Buckingham Fountain spouts water high into the air.  If you are visiting in the evening, there’s a light show too!

Chicago Buckingham Fountain

From the parks, you can take a stroll along the Lake Michigan Lakefront Trail, a walking and cycling path that goes on for 18 miles!  Needless to say, we didn’t walk the 18 miles, I doubt we even went a mile!  It was a nice walk away from the busy city streets and we could have a nose at big fancy boats in the harbour instead!

From here you could visit:

🗺600 E Grand Ave, Chicago, IL 60611, United States

Navy PierNavy Pier is GINORMOUS! I’m used to the UK’s little pleasure piers but Navy Pier just seemed huge!  There’s an indoor area with shops, restaurants, a theatre, an Imax, gardens and museums, as well an outdoor area with fair ground rides and lots of opportunities for boat trips on Lake Michigan.  You could spend a whole day here alone!

Navy Pier Chicago


…turn back into the city and take the Chicago Riverwalk.  There is plenty to do around the Chicago River.  There are restaurants, cafes, boat trips, interesting architecture etc. Chicago River Architecture Cruises are a really popular tour to go on while in Chicago. We had lunch at Dick’s Last Resort, which is great if you like sarcasm and being insulted…and that’s not sarcasm, it’s a really fun restaurant!

If you’re in to architecture, my friend Theresa wrote a book about the history of some of Chicago’s landmarks: Living Landmarks of Chicago: Tantalizing Tales and Skyscraper Stories; Bringing Chicago’s Landmarks to Life

Route 66 Chicago River

Day 2 in Chicago

Day 1 is a whistle stop tour of some of the main sites in Chicago and our exact itinerary for when we only had one full day in Chicago.  I have since been back to Chicago several times and seen more!  If you have 2 days in Chicago there are lots of other options for things to do.

There are many museums in Chicago, if you love animals Lincoln Park Zoo is a great free zoo and Sprinkles has a ‘cupcake ATM’ which is fun.  If you are looking for things to do in Chicago at night, the Blue Man Group stage show is awesome. The House of Blues music venue often has live bands. I haven’t been yet but there’s a ‘Speakeasy’ magic bar and venue that you enter through a laundrette, that I’ve heard great things about it! One of my personal favourite ways to see a city when I only have a day or two, is on a Segway tour!

Chicago skyline Lincoln Park

Save Money With Chicago CityPASS

If you are looking at visiting some of the museums as well while in Chicago, both 360 Chicago and Skydeck are part of the Chicago CityPASS. With CityPASS you can save up to 49% on entrance fees to 5 Chicago attractions! Click the image below to find out more.

The pass includes entrance to:

Shedd Aquarium

Field Museum

Plus 3 attractions from: Skydeck Chicago, Art Institute of Chicago, Museum of Science and Industry, 360 Chicago, Adler Planetarium.

You could easily fill 2 days in Chicago, just with the museums!

Chicago Murals

🗺2226 N Milwaukee Ave, Chicago, IL 60647, United States

When taking the blue CTA Metro line to or from the airport into Downtown, if you jump off at the California stop, just below the rail line you’ll see a retro ‘Greetings From Chicago’ mural.  There are a few other murals in this area.  In fact you’ll see loads of Chicago murals from the CTA between Western and California.

Other Route 66 Resources

Route 66 Chicago to St Louis – 9 Must See Stops in Illinois USA

Route 66 Itinerary: How Long Does It Take To Drive Route 66?

Route 66 Budget | How Much Does It Cost To Do Route 66 USA Road Trip?

Must See Route 66 Roadside Attractions

Real Life Route 66 ‘Cars’ Movie Locations | The Places That Inspired Radiator Springs

Kylie Signature

Inspired by this 2 days in chicago Route 66 guide? Pin it for later!

2 Days in Chicago Itinerary

14 thoughts on “Route 66 Chicago: A Guide To The Start of Route 66 & 2 Days In Chicago!

    1. It seems that they are making more fuss of it only recently! I’ve been to Chicago a few times too but the last time seemed to have signs everywhere!

    1. It seems in the last few years more and more people are travelling for it. Chicago seems to have embraced it more in the last couple of years!

      1. I really want to do the one in Minnesota because I love the twin cities region. Im doing the one in Seattle in March

      2. Oh i could definitely see that happening. But you finished. I wasn’t prepared for humidity but think freezing cold is worse to run in.

Leave a Reply