Chicago is a must-visit destination, renowned for its iconic architecture and vibrant food and art scene. It also serves as America’s largest rail hub, with 15 rail lines converging at Chicago Union Station. If you plan a trip to this beautiful city, consider including a train journey. In this post, we will share our experiences on the Amtrak Empire Builder route, along with recommendations for places to stay and things to do in the charming city of Chicago.

Arriving in Chicago 

We have always been intrigued by Chicago, but our interest piqued when one of our favorite bands announced a concert at Wrigley Field. Due to time constraints, we opted to fly to Chicago instead of taking the train, saving that for the end of our trip.

We were nervous about using public transit upon arriving at the airport, so we chose a taxi to our hotel. This choice quickly backfired as our driver navigated wildly through traffic while other drivers honked and shouted at us, giving us a taste of the city’s hustle and bustle.

After arriving at our hotel in the quieter Lincoln Park area, we settled in and grabbed a bite. Then, we walked a few blocks to catch the L Train downtown. We had prepared an itinerary of must-see attractions and were eager to begin our exploration. Based on our research and experiences, here’s a list of activities, places to stay, and dining options in Chicago.

Things to do:

• Willis Tower Skydeck – Willis Tower, formerly the Sears Tower, is a famous Chicago skyscraper that was the tallest building in the world for nearly 25 years. The Skydeck on the 103rd floor features a glass balcony with stunning city views. Tickets start at $36; buying them online in advance is best. We purchased a fast pass to skip the lines, which was worth it!

• Lakefront Trail – The 18-mile paved trail along the Lake Michigan shoreline runs from Ardmore Street to 71st Street, connecting popular parks and beaches like South Shore Beach, North Avenue Beach, and the Lincoln Park Zoo. It’s a favorite spot for walkers, runners, bikers, and skateboarders.

• North Avenue Beach – North Avenue Beach, located at 1600 N. Jean-Baptiste Pointe DuSable Lake Shore Drive in Lincoln Park, is an excellent spot for swimming, sunbathing, and enjoying views of Lake Michigan. It was our favorite place to watch the sunset and photograph the city skyline.

• Chicago History Museum – Founded in 1856, the museum was rebuilt after the Great Chicago Fire of 1871 and is now located at 1601 North Clark Street in Lincoln Park. It offers interactive exhibits to explore Chicago’s history. Admission is $19 for adults, $17 for seniors (65+) and students, and free for children 12 and under.
• Millennium Park – In Grant Park at 201 E. Randolph St., this 24-acre park features the famous Cloud Gate, or “the Bean,” a sculpture that reflects the city skyline and nearby visitors, perfect for photos. Arrive early to avoid crowds. You can also check out the Crown Fountain, which honors Chicago’s residents with rotating LED screens, and enjoy winter activities like ice skating and carousel rides at Millennium Park.

• Art Institute of Chicago – On the corner of Millennium Park, the Art Institute of Chicago stands as one of the largest and highest-ranked art museums in the U.S. It features works by renowned artists like Monet, Picasso, Van Gogh, and Matisse, as well as iconic pieces such as Grant Wood’s “American Gothic.” Fans of “Ferris Bueller’s Day Off” will remember the museum from the film. Ticket prices are $32 for adults, $26 for seniors, and free for students and youth.

• Chicago Riverwalk – The path stretches 1.25 miles from Lake Street to the Lake Michigan waterfront, providing stunning architectural views along the picturesque Chicago River. Along the way, you’ll find numerous outdoor cafés, wineries, and breweries where you can relax and enjoy the scenery while watching boats and kayakers pass by.

• Chicago River Boat Architecture Tour – We didn’t take the River Boat tour, but others highly recommended it. These tours run from May to October and provide a great way to enjoy the views and learn about the history of the skyscrapers. There are various options, so you may want to check out Trip Advisor for tour details, options, and reviews.

• The Magnificent Mile – The Magnificent Mile is a renowned shopping area featuring a variety of stores, restaurants, and historic hotels. It stretches between the Michigan Avenue Bridge and Oak Street, with notable buildings including Water Tower Place, the Observation Deck at 360 Chicago, The Drake Hotel, and Tribune Tower.

• Wrigley Field – Wrigley Field is the iconic home of the Chicago Cubs, opening its doors in 1914. You can enjoy guided tours, including stops at the seating bowl, press box, bleachers, and both the Cubs’ and visitors’ clubhouses, with a chance to step onto the field.

• Navy Pier -Located on Lake Michigan, Navy Pier is a top tourist destination. In addition to the incredible lake and city skyline views, this Chicago landmark features the following fun activities for all ages:

• • See the sites from the iconic Centennial Wheel
  • Experience the FlyOver Chicago ride
  • Get lost in Amazing Chicago’s Funhouse Maze
  • Play and learn something new at the Chicago Children’s Museum
  • Catch a show at the Chicago Shakespeare Theater
  • Cruise around the lake and river on a scenic boat tour
  • Visit Pier Park for miniature golf and other family fun
  • Enjoy the beautiful scenery and fountains at Polk Bros Park
  • Grab refreshments at restaurants, bars, or beer gardens

🌟 Visitors can also catch a summertime fireworks show on Wednesdays and Saturdays between Memorial Day and Labor Day.

TIP:  Buy a Chicago CityPASS for $134 for 50% savings on admission to top Chicago attractions, including the SkyDeck (expedited admission), 360 Chicago Observation Deck, Art Institute of Chicago, Shedd Aquarium, and an architecture cruise, among other attractions.

Where to Stay:

• Canopy by Hilton Central Loop– This building was initially constructed as the headquarters for the Chicago and Northwestern Railways. It is located at 226 West Jackson Boulevard, just a block and a half from the train station and directly across the street from Willis Tower. The building also features an on-site restaurant and bar.
• Hilton Garden Inn Central Loop– Located at 254 S. Franklin St., just a block from Union Station, this hotel is in a historic building across the street from Willis Tower. Additionally, the hotel features a rooftop bar and lounge.
• Hampton Inn West Loop – This modern hotel offers stunning skyline views of downtown Chicago, with additional charges for view rooms. Located at 116 N Jefferson, it’s just a few blocks from the train station and close to art galleries, theaters, shopping, restaurants, and parks. The hotel includes an indoor pool and a rooftop terrace.
• The Homewood Suites by Hilton West Loop– Homewood Suites, located in the heart of downtown Chicago, offers a self-pour bar and an indoor pool. The address is 118 N. Jefferson. The hotel features studio suites equipped with a sofa and a kitchenette.
• Hotel Versey–  For a budget-friendly stay near Lincoln Park, consider Hotel Versey at 644 W. Diversey Parkway, close to public transit. The hotel offers clean rooms and comfortable beds, with Trader Joe’s just across the street for snacks. It’s also within walking distance of the Lake Michigan waterfront, Lakeshore Trail, and Lincoln Park Zoo.

Where to Eat and Drink:

If you’re a foodie, Chicago is the perfect destination. Locals are passionate about deep-dish pizza, Italian beef sandwiches, and hot dogs. The city offers a wide array of exceptional dining options. Here’s a list of popular spots to sample these unique Windy City foods:

Pequod’s Pizza – Known for their deep-dish pizza and caramelized crust.  There are two locations – one on Clybourn Ave in the Lincoln Park Neighborhood and the other in the suburb of Morton Grove.

Lou Malnati’s – Another popular restaurant famous for its deep-dish pizza, with over twenty locations in Chicago, including the Wrigley Building, Lincoln Park on Wrightwood Avenue, and several Downtown spots.

Giordano’s Pizza – Serves Chicago-style deep dish stuffed pizza with multiple locations in the heart of the city, including Navy Pier, E. Randolph St., W. Jackson Blvd., N. Rush St., and W. Van Buren.

Portillo’s – Portillo’s is known for its Italian beef, burgers, chopped salads, Chicago-style hot dogs, and homemade chocolate cakes. With 46 locations in Chicago, you can easily find one nearby. The Portillo’s at 520 W. Taylor St., near Chicago Union Station, is perfect for a quick meal before your train.

Jimmy’s Red Hots – Jimmy’s offers authentic Chicago-style hot dogs, Polish sausages, and hand-cut fries—fast and affordable food that embodies the Chicago experience. Their website states, “Jimmy’s is a purist hot dog stand: no seating, no charred items, and absolutely no ketchup!” They do provide a homemade habanero hot sauce for dipping fries.

Al’s #1 Italian Beef – A well-known restaurant famous for its hearty Italian beef sandwiches, Au Jus dip, hot dogs, and fresh-cut fries. Locations include 3420 Clark St. near Wrigley Field, 1079 W. Taylor in Little Italy, and 548 Wells St. downtown. Since opening in 1938 as a family-owned beef stand in Little Italy, it has become a top spot for Italian beef sandwiches.

Lou Mitchell’s – This is a popular diner known for breakfast and lunch, where guests are served a portion of their famous donut holes as soon as they are seated. The portions are generous, and both the food and service are excellent. Be prepared to wait for a table, as this place tends to get busy!

Bavette’s Bar & Boeuf -For an upscale dining experience, Bavette’s is regarded as one of Chicago’s finest steakhouses. It is ideal for celebrating a special occasion or enjoying a romantic dinner with your partner. Be sure to call several months in advance to make your reservations!

The Berghoff Restaurant – Opened in 1898, The Berghoff is widely known for its authentic German cuisine and cozy ambiance.  Located at 17 W. Adams St., this restaurant has a fascinating history as one of the oldest family-run businesses in the Country. Reservations are recommended, as this place fills up quickly!

In 2018, Adams Street Brewery opened within the Berghoff Restaurant. The brewery offers diverse draft beers, cocktails, wine, and ciders. It’s an excellent spot to take a break from sightseeing and enjoy refreshments.

Sheffield’s Beer & Wine Garden – Sheffield’s, located at 3258 N. Sheffield Ave, was a highlight of our Chicago visit. It’s a great spot for BBQ and drinks near Wrigley Field. Recognized by Esquire Magazine as one of the “Best 100 Bars in America,” it offers indoor and outdoor seating, tasty food and drinks, and excellent service.

How to Get Around:

Chicago’s transportation infrastructure is unparalleled in the U.S., making public transit an ideal way to explore the city.  The buses and trains of the Chicago Transit Authority (CTA), L trains, and Metra Regional Trains are affordable. Once we understood the city’s layout, navigating public transit became easy. We enjoyed riding the elevated L train and watching the city pass by outside.

TIP: Download the Ventra transit app to help plan your routes and purchase tickets. You can also buy Ventra cards at the train stations. Taxis, water taxis, and Uber are other, more expensive transportation options.

Boarding the Train at Chicago Union Station

On our final day in the beautiful, windy city, we prepared for our long-distance train ride home. We stocked up on snacks and drinks at Trader Joe’s and packed our bags. Then, we hopped on a public transit train heading to Union Station.

We arrived at Chicago Union Station 30 minutes before departure, but had trouble finding the entrance due to construction. After entering the wrong door, we sought help from an Amtrak employee, who directed us to the correct boarding line for our Sleeper Car tickets.

We later discovered that passengers should wait for their trains in the Great Hall (see photo below). In this area, you can check the departure boards to find your train’s status, and it’s essential to listen for announcements regarding boarding times and locations. If you find yourself confused, as we were, please don’t hesitate to ask an Amtrak employee for help.

Empire Builder Route – Chicago to Tacoma

The Amtrak Empire Builder is a daily long-distance Amtrak route through the northern parts of the United States, connecting Chicago to parts of Washington and Oregon.  The views along this route, particularly scenic through the Rocky Mountains, Cascade Mountains, and Columbia River Gorge, are breathtaking. It’s a fantastic way to enjoy the Pacific Northwest scenery.

After boarding the train, we stored our luggage in the downstairs rack and brought our backpacks and overnight gear to our roomette. For more details on Roomette Accommodations on the Amtrak Empire Builder, check out our related post. We began our train journey in the vibrant city of Chicago, which soon shifted to the scenic landscapes of the rural Midwest. Along the way, we enjoyed the views of charming lakeside towns in Wisconsin and the majestic Mississippi River.

About an hour into our train ride, our room attendant swung by to take our dinner reservation for the Dining Car. When it was finally time for dinner, we headed down there and waited to be seated. We ended up with a lovely couple from Paducah, Kentucky, and it was great sharing stories about our travels, the empty-nest phase, and hitting that milestone of turning 50.

After dinner, we returned to our roomettes, where our beds had been prepared. We enjoyed a drink before climbing into our bunks. However, our roomette was warm and muggy, leading to a restless night. This was quite different from our previous experiences in sleeper cars, which had typically been more comfortable, even feeling a bit cool at night.

The next morning, we enjoyed a refreshing break in Minot, North Dakota, where the cool air was a welcome change. The stop lasted about 45 minutes for refueling and a mechanical check. During this time, we enjoyed chatting with one of the mechanics and our room attendant. It was a treat to hear their stories about their families, hometown life, and experiences in the train industry.

Eventually, the train departed from the Minot station, chugging along through the North Dakota plains. The Wi-Fi was spotty, but we could usually access the internet when we passed through towns. Most of the time, however, we had to rely on our mobile data to stay connected. We had packed books and games to keep us entertained, but the scenery outside the train was usually captivating enough.

As we traveled through Glacier National Park around dinner time, we were treated to a breathtaking sunset. Our dinner companions were a single mother and her son, returning home after a family visit to Chicago. We met this duo several more times during our journey, eventually exchanging phone numbers and agreeing to stay in touch. You never know what kind of interesting people you will encounter on a train!

The next morning, we woke to a beautiful sunrise in Eastern Washington. The Dining Car was dropped off in Spokane, and we received a boxed breakfast of pastries and juice. We then went to the Observation Car to take in the breathtaking views of the Columbia River Gorge, surrounded by quiet and reflective passengers who shared a mutual sense of awe for the stunning Pacific Northwest scenery.

Our train eventually arrived at the Portland Union Station.  We decided to store our bags and wander the road for a bite.  Our sleeper car reservation included free access to the Metropolitan Lounge, where we were able to store luggage at no cost.  We headed down to the Backwoods Brewing Company.  The pulled pork sandwich, sweet potato fries, tots plate, and three-cheese mac and cheese were all delicious. However, the S’more Golden Stout was the favorite part of this experience!

After a quick lunch, we headed back to Union Station and kicked back in the comfy couches of the Metropolitan Lounge while waiting for our train home. We were pleasantly surprised that there were no delays on our route from Chicago, especially since the Empire Builder usually has a pretty bad track record with that. Thankfully, everything went smoothly, and we enjoyed our journey home!

Takeaways

We had a wonderful visit to Chicago, followed by a scenic train ride home. Chicago boasts world-class attractions, fascinating neighborhoods, and a vibrant cultural scene. The city’s food offerings make it worth a visit, with various highly rated dining experiences available.

Additionally, traveling to and from Chicago by rail is easy, and navigating the city using public transportation is convenient. Because of this, there’s no reason not to place Chicago at the top of your travel list.

We hope this guide helps you plan your next trip to Chicago and encourages you to include a scenic train ride in your itinerary. We’re confident you will love it as much as we did!

Please drop a comment or let us know if you have questions below!