Route 66 Chicago: A Guide To The Start Of The Route & Seeing Chicago In A Day!

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 Chicago in a day? Hopefully I can answer some of those questions in this Route 66 Chicago guide!

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/start your journey

Route 66 start sign

Chicago in a day

Landing in Chicago

Where To Stay/Start Your Route 66 Journey

Here are a couple of my suggestions for how you could start your Route 66 journey:

  • 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) to the larger ‘premium’ chains such as the Hilton and the Marriott ($120+), most having 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 (saving us the cost of 1 day’s rental as we collected it on day 2) and 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 now live 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 but 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 recently started 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.

Chicago CTA train

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.  The easiest way is to pay in cash.  Some booths have people, others you’ll need the correct change.  If they are I-Pass only, 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.

Route 66 Start Sign

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.  The location of the sign has slightly moved recently.  It used to have its own post and was set slightly back from S Michigan Ave.

Chicago Route 66 Start

The post has now completely gone and the sign has moved onto the other side of the street, right on the corner of S Michigan Ave.  It’s also ABOVE a cross walk traffic light.  The area can be quite busy, which makes it a little harder to get a picture with it.

Route 66 Chicago Start Sign New

*Edit* Since writing I believe the sign is back in the original location on its own pole…I’m not sure if the traffic light one has therefore since been removed because of this!

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.

Route 66 Chicago Illinois Sign

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.

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.

Chicago Route 66 Adams St

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.

Chicago In A Day

Embarking on a full journey across the USA, you may not have a huge amount of time in the city, so here are a few options of things do to in Chicago in a day.

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!

Skydeck The Ledge at the Willis Tower Chicago

Related ReadingSkydeck or 360 Chicago: Which Chicago Observation Deck is Better?

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!

Chicago Crown Fountain

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!

Chicago Cloud Gate - The Bean

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.

Chicago Cloud Gate at Night

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 BP Footbridge

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!

Chicago Mini Golf

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).

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:

Navy Pier Chicago

Navy Pier – Navy 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!


Route 66 Chicago River

…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. 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!

Chicago skyline Lincoln Park

This was everything we did in Chicago in a day.  I have since been back to Chicago and seen more.  There are lots of museums, Lincoln Park Zoo is a great free zoo, Sprinkles has a ‘cupcake ATM’.  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!

Chicago Murals

Chicago Murals California CTA

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.

Chicago Mural

Other Route 66 Resources

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

Route 66 Attractions: 8 States, 8 Roadside Stops

Real Life Disney ‘Cars’ Movie Locations on US Route 66!

Kylie Signature

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Route 66 Chicago USA: Chicago in a day.  A guide to the start of Route 66!

Route 66 Chicago USA. A guide to Chicago in a day and tips for those driving Route 66 Chicago Route 66: One day in Chicago guide and where to stay when driving Route 66 Route 66 Chicago USA: A guide to seeing Chicago in a day and tips for starting Route 66!

19 thoughts on “Route 66 Chicago: A Guide To The Start Of The Route & Seeing Chicago In A Day!

      1. 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.


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