And so it began – our Route 66 journey. We flew from Helsinki to Chicago, where we had booked accommodation at Chicago Getaway Hostel in the Lincoln Park area.
The immigration procedures went smoothly, although we were a bit nervous given the stories we had heard about potentially thorough questioning. Fortunately, we weren’t asked anything out of the ordinary, and everything went effortlessly.
From the airport, we took a taxi to our accommodation, located on a cozy and beautiful street lined with trees and small apartment buildings. The street gave off a New York vibe, although we had never been to NYC, and our impression was solely based on TV shows and movies 😄
The hostel itself was clean in its common areas, and our private room was also decently tidy. The shared bathroom facilities were somewhat typical for a hostel—slightly worn and could have been cleaner, but it served its purpose well. The distance from here to downtown Chicago was just under 6 km.
We had booked three nights in Chicago, and we had also reserved a car for the remainder of our trip onward. The car would be returned at Los Angeles International Airport when we headed back home.
On both days, we opted to walk from the hostel to downtown. Along the way, we passed through Lincoln Park, a large and beautiful park area along the shores of Lake Michigan. The park features small ponds and numerous trails. While the park also houses a zoo, we didn’t visit it, unlike the Farm in the Zoo domestic animal exhibits, where the atmosphere was more like being on a farm within the bustling city of Chicago.
Chicago attractions we recommend
The Magnificent Mile & Riverwalk
The Magnificent Mile is a stretch of North Michigan Avenue north of the Chicago River, known as one of Chicago’s most popular tourist attractions and a hub of the city’s business district. It boasts numerous shops, restaurants, hotels, and of course, bustling crowds. Also, the riverfront is a must-visit. Strolling along the Riverwalk offers views of the winding river amidst skyscrapers and beautiful cityscapes.
Cloud Gate – Millennium Park
Millennium Park is a central park in the city where the famous Cloud Gate sculpture, affectionately known as The Bean, is located. You’ve probably seen pictures of Chicago featuring a large silver bean-shaped sculpture—that’s it! The sculpture, made up of 168 stainless steel plates, reflects the surrounding cityscape. The park hosts many events, so it’s worth checking ahead to see what might be happening during your visit.
Willis Tower
Willis Tower is one of Chicago’s most iconic landmarks. Standing over 400 meters tall, it offers stunning views of the city from its observation deck. Visiting the skydeck costs around $25 per person and is definitely worth it. You can peacefully admire city views through large windows in every direction from the top. The experience of riding the elevator up to such a height alone is memorable. We can guarantee your ears will pop. At the top, there’s also a glass box extension where you can stand “over nothing” and gaze down through the glass floor to the street below. Stepping onto the glass floor was admittedly a bit nerve-wracking but was an absolutely incredible experience.
Navy Pier
Navy Pier is a large pier on the shore of Lake Michigan, packed with activities. It features a Ferris wheel, numerous restaurants, cafes, shops, theaters, a hotel, a museum, and more. The area is exceptionally pleasant with beautiful views of the city. In the evening, this place is wonderfully atmospheric, with the city skyline beautifully lit up. The highlight of the evening was an amazing fireworks show. During the summer, fireworks are displayed every Wednesday at 9:00 PM and every Saturday at 10:00 PM.
Grant Park
Grant Park is a beautiful park area that includes the famous Buckingham Fountain and offers scenic views of the city’s skyscrapers. This is worth combining with a visit to see the Cloud Gate sculpture, as the area is essentially part of the same large park.
Start of Route 66 Sign
And of course, since we were embarking on Route 66, this starting point was important! So, if you’re on your way to Route 66, this is a must-visit. From here, the legendary road trip was ready to begin.
We highly recommend exploring Chicago on foot. The city is magnificent, with plenty to see, and there are many attractions and streets not listed here. We can’t speak to public transportation as we walked everywhere throughout our stay. We only took a taxi back to the hostel in the evenings.
