Chicago is a true bucket-list destination, from its iconic architecture to its vibrant food and art scene. It is also America’s largest rail hub, with 15 rail lines ending at the Chicago Union Station. So, if you’re planning a trip to this beautiful city, consider incorporating a train journey into your itinerary. In this post, we’ll share our experiences on the Amtrak Empire Builder route and tips for places to stay and things to do in the enchanting city of Chicago.

Arriving in Chicago 

We’ve always been intrigued by Chicago. However, it wasn’t until one of our favorite bands announced their tour and plans to play at Wrigley Field that we seriously considered planning a trip there. Due to time constraints and our concert being on a weekday, we decided to book a plane ride to Chicago. By saving the train journey for the end of our trip, we had one more thing to look forward to—a more pleasant experience than dealing with the hassles of traveling by plane.

After arriving at the airport in Chicago, we were nervous to hop on city transit right away.  Without knowing what to expect or having a good feel for the place, we thought a taxi would be an easier ride to our hotel. We quickly regretted this decision as our taxi driver chatted with us while impulsively veering in and out of lanes, dodging traffic. All the while, other drivers were honking and yelling obscenities at our cab driver.  We felt the hustle and bustle of the city at that moment.

We arrived at our hotel and were relieved to have booked our accommodations in a less busy part of the city.  We’d chosen a hotel near Lincoln Park, between the main downtown area and Wrigley Field.  After settling in and grabbing a bite to eat, we walked a few blocks down the road to catch the L Train downtown. While planning our trip, we’d created an itinerary of must-see places and felt like we needed to get right to it. Based on our research and experience, the following is a list of activities, places to stay, and where to eat and drink while in Chicago.

Things to do:

• Willis Tower Skydeck – One of the most iconic skyscrapers in Chicago, Willis Tower (formerly known as Sears Tower) was the tallest building in the world for almost 25 years.  On the 103rd floor, there’s an observation deck called “the Skydeck” where you can walk out on a glass balcony and look down on the city below.  Tickets start at $36, and we’d recommend you pre-purchase tickets online. We paid extra for the fast pass, allowing us to skip the lines.  Worth it, in our opinion!

• Lakefront Trail – An 18-mile paved trail along the Lake Michigan Shoreline.  The path runs from Ardmore Street to 71st Street.  The trail connects many of Chicago’s popular parks and beaches, including South Shore Beach, North Avenue Beach, Maggie Daley Park, Grant Park, Shedd Aquarium, and the Lincoln Park Zoo. The trail is a popular spot for walkers, runners, bikers, and skateboarders.

• North Avenue Beach – Located in Lincoln Park at 1600 N. Jean-Baptiste Pointe DuSable Lake Shore Drive, North Avenue Beach is a popular spot for swimming, sunbathing, and enjoying the gorgeous Lake Michigan views.  This was our favorite place to catch the sunset and to snap evening photos of the magical city skyline.

• Chicago History Museum – Founded in 1856, the original museum was destroyed in the Great Chicago Fire of 1871. Now located in Lincoln Park at 1601 North Clark Street, the museum offers fun, interactive exhibits and is a great way to learn about Chicago’s rich history.  Admission is $19 for Adults, $17 for Seniors (65+) and Students, and FREE for children (12 and under).
• Millenium Park – Located inside Grant Park at 201 E. Randolph St, this 24-acre park is home to the famous Cloud Gate (also known as “the Bean”).  The Bean is a sculpture inspired by liquid mercury and offers cool reflections of the city skyline and people standing nearby.  A popular spot for photos.  We’d recommend you show up earlier in the day before crowds arrive. You can also visit the interesting Crown Fountain, which pays tribute to the people of Chicago on rotating LED screens.  In the winter, Millenium Park offers additional activities such as ice skating and carousel rides.

• Art Institute of Chicago – On the corner of Millenium Park, you’ll find the incredible Art Institute of Chicago – one of the largest, oldest, and highest-ranked art museums in the United States.  Displays include Monet, Picasso, Van Gogh, and Matisse as well as iconic pieces of work like Grant Wood’s “American Gothic” and George Seurat’s “A Sunday on La Grande Jatte”.  If you’re a fan of the John Hughes movie “Ferris Bueller’s Day Off”, you’ll remember Ferris and his friends visited the Art Museum while they played hooky from school. Tickets are $32 for adults, $26 for seniors, and FREE entry for students and youth.

• Chicago Riverwalk – A 1.25-mile path from Lake Street to the Lake Michigan waterfront. This path offers incredible views of the architecture along the banks of the scenic Chicago River.  There are plenty of outdoor cafes, wineries, and breweries to relax at while watching the boats and kayakers pass by.

• Chicago River Boat Architecture Tour – While we didn’t end up doing the River Boat tour, this was by far the activity that others recommended to us the most. Boat tours typically operate from May through October and are a great way to get out on the water, enjoy the views, and learn a little bit about the history of the towering skyscrapers.  There are a variety of options, so you may want to check out Trip Advisor for tour details, options, and reviews.

• The Magnificent Mile – One of the most famous shopping areas in the world, The Magnificent Mile is home to a variety of stores, restaurants, coffee shops, and historic hotels and architecture. The shopping area is located between the Michigan Avenue Bridge and Oak Street.  You’ll find popular buildings along this stretch, such as Water Tower Place, another Observation Deck at 360 Chicago, The Drake Hotel, and Tribune Tower.

• Wrigley Field – Home of Major League Baseball’s Chicago Cubs.  This popular stadium opened in 1914 and is full of nostalgia.  You can take a guided tour of Wrigley Field that may include visits to the seating bowl, press box, bleachers, visitor’s clubhouse, Cubs’ clubhouse, and Cubs’ dugout, and a chance to step out on 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 the 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 originally constructed as office headquarters for the Chicago and Northwester Railways. Located at 226 West Jackson Blvd, just a block and a half from the train station and across the street from Willis Tower.  Features an on-sight restaurant and bar.
• Hilton Garden Inn Central Loop– Located at 254 S. Franklin St., just a block from Union Station.  This hotel is also inside a historic building and across the Street from Willis Tower. The hotel also features a rooftop bar/lounge.
• Hampton Inn West Loop – This modern hotel offers beautiful skyline views of Chicago’s downtown area, although you may have to pay a little extra for a room with a view.  It’s located at 116 N Jefferson, just a few blocks from the train station and with easy access to art galleries, theaters, shopping, restaurants, and parks. The hotel features an indoor pool and a rooftop terrace.
• The Homewood Suites by Hilton West Loop– Offering a self-pour bar and indoor pool, the Homewood Suites is another hotel located in the heart of downtown Chicago.  The address is 118 N. Jefferson.  The hotel offers studio suites with a couch and kitchenette.
• Hotel Versey–  For a more budget-friendly option near Lincoln Park, you may want to consider the Hotel Versey, located at 644 W. Diversey Pkwy, close to public transit stations.  The hotel provides basic accommodations, but the beds were comfortable, and the rooms were clean.  Trader Joe’s is right across the street if you need somewhere to stock up on snacks and drinks. The hotel is also an easy walk to the Lake Michigan Waterfront, Lakeshore Trail, and Lincoln Park Zoo.

Where to Eat and Drink:

If you consider yourself a foodie, then Chicago is the place for you. Chicagoans are passionate about their deep-dish pizza, Italian beef sandwiches, and hot dogs.  We could spend weeks eating our way through Chicago because the food options are just that amazing. The following is a list of some of the more popular places to dine and try out foods that are uniquely special to the windy city:

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 highly rated restaurant serving deep dish pizza.  Lou Malnati’s has over locations in Chicago. Chicago has a location inside the Wrigley Building on Michigan Avenue, one in the Lincoln Park area on Wrightwood Avenue, and several located in the Downtown area on Michigan Avenue, N. Wells St, N. State St, and S. State St..

Giordano’s Pizza – Serving Chicago-style deep dish stuffed pizza, Giordano’s also offers multiple locations in the heart of Chicago.  You can visit restaurant locations at the Navy Pier on E. Grand Ave, on E. Randolph St., W. Jackson Blvd., N. Rush St., and W. Van Buren, in addition to other locations throughout the City.

Portillo’s – Home to Chicago’s famous Italian beef, burgers, chopped salads, and Chicago-style hot dogs. They also have amazing homemade chocolate cakes on the menu. There are 46 locations in Chicago, so you’ll likely find one in most areas.  The Portillo’s, which is close to the Chicago Union Station on 520 W. Taylor St., is a great place to grab a bit before you catch your train.

Jimmy’s Red Hots – Serving up delicious authentic Chicago-style hot dogs, polish sausages, and hand-cut fries.  It offers fast and affordable food that’s part of the classic Chicago experience. According to Jimmy’s website, “Jimmy’s is a purist hot-dog stand. No seating, no char-anything, and for crissakes, no ketchup!” They do have a homemade habanero hot sauce to dip fries in.

Al’s #1 Italian Beef – A restaurant known for overstuffed 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. in the downtown area, in addition to other places around town. The original restaurant opened in 1938 as a family-owned beef stand in Little Italy and has been considered a top-tier place for Italian Beef sandwiches since then.

Lou Mitchell’s – A popular breakfast and lunch diner, where they bring you a serving of their famous donut holes as soon as you’re seated.  Portions are large, and food and service are outstanding.  Expect to wait for a seat, as this place gets quite busy!

Bavette’s Bar & Boeuf – For a more upscale experience, Bavette’s is considered one of Chicago’s best steakhouses. The perfect spot to celebrate a special occasion or have an intimate dinner with your significant other.  Call several months ahead to make your reservations!

The Berghoff Restaurant – Opened in 1898, this restaurant is widely known for its authentic German cuisine and cozy ambiance.  Located at 17 W. Adams St., this restaurant has an interesting 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 was opened inside the Berghoff Restaurant.  The Brewery features a variety of draft beers, cocktails, wine, and ciders. A great place to take a break from sightseeing and grab refreshments.

Sheffield’s Beer & Wine Garden – Located at 3258 N. Sheffield Ave,  Sheffield’s was one of our favorite places for food and drinks during our visit to Chicago.  It’s a perfect place to stop for drinks and BBQ if you’re visiting Wrigley Field.  Sheffield’s was voted by Esquire Magazine as one of the “Best 100 Bars in America” and features indoor and outdoor seating areas, delicious 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) buses, L trains, and Metra Regional Trains are the most affordable way to get around. Once we had a general idea of the layout of the city, we found public transit very easy to use. We especially loved riding the elevated L train and watching the city go by outside our windows. 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 transportation options but are a bit more expensive.

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 had our bags packed up and ready to go. We hopped on a public transit train bound for Union Station.

Arriving at the Chicago Union Station about 30 minutes before departure, we struggled to find the entrance. There was quite a bit of construction and no clear indication to which door would lead us to where we needed to be.  Unfortunately, we entered the wrong door and had to find an Amtrak employee to guide us to our departure location.  We had priority boarding with our Sleeper Car tickets, so she directed us straight to our boarding line.

We later found out that passengers are supposed to wait for their trains in the Great Hall (pictured below).  You can view departure boards to keep an eye on the status of your train, and you will need to listen for announcements about boarding times and locations.  If you find yourselves confused, like we were, 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 states.  The views along this route, particularly through the Rocky Mountains, Cascade Mountains, and Columbia River Gorge, are stunning.  It’s a wonderful way to take in the Pacific Northwest scenery.

After boarding the train, we stowed our luggage in the downstairs rack and brought our backpacks and overnight gear with us to our roomette. For more details on Roomette Accommodations on the Amtrak Empire Builder, check out our related post. We enjoyed starting our train journey in the big city, passing by the Chicago River, and watching as the scenery changed to more rural midwest views. The train passed by picturesque lakeside towns in Wisconsin and provided expansive views of the Mississippi River.

About an hour into our train ride, our room attendant stopped by to take our reservation for dinner in the Dining Car. Once our prescheduled dinner time rolled around, we wandered down to the Dining Car and waited to be seated,  We were seated with a nice couple from Paducah, Kentucky, who we enjoyed sharing mutual stories about travel, empty-nesting, and recently turning 50.

After dinner, we returned to our roomettes, where our beds had been prepared for us.  We enjoyed a drink before climbing into our bunks. It was warm and muggy in our roomette, leading to a bit of a restless night. This was different from our previous sleeper car experiences. Typically, we’ve experienced more comfortable temperatures, even getting a bit cool in the sleeper car at night.

The next morning, we enjoyed a fresh air break in Minot, North Dakota.  The cool air in Minot was a refreshing change.  The stop took about 45 minutes for a refuel and mechanical check. During this time, enjoyed chatting with the one of the mechanics as well as our room attendant.  What a treat to hear their stories about their families, life in their hometowns, and working in the train industry.

Eventually, the train departed from the Minot station, chugging along through the North Dakota Plains.  The WiFi 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’d packed books and games to keep us busy, but typically found the scenery outside the train to be entertainment enough.

We passed through Glacier National Park around dinner time and were greeted by a glorious sunset.  Our dinner companions this time around were a single mom and her son, who were making their journey home after a visit with family in Chicago.  We ran into these two several other times during our journey, eventually exchanging phone numbers and agreeing to keep in contact.  You never know what kind of characters you will connect with on a train!

The next morning, we woke up to the most beautiful sunrise in Eastern Washington. The Dining Car had been dropped off in Spokane, so there were no freshly cooked meals available for the last leg of the trip.  We received a boxed breakfast of pastries and juice and headed into the Observation Car to enjoy the breathtaking views as we chugged alongside through the Columbia River Gorge.  The passengers in the car were quiet and pensive, a mutual sense of awe at the stunning Pacific Northwest scenery.

Our train eventually arrived at the Portland Union Station.  We decided to store our bags and wander down the road for a bite to eat.  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-n-cheese were all delicious.  But let me tell you about the S’more Golden Stout – this beer is just the absolute best!   

Following a quick lunch, we made our way back to the Union Station. We relaxed on the comfy couches in the Metropolitan lounge while we waited for the arrival of our train ride home.  We were pleasantly surprised that there were no delays on our long-distance route home from Chicago.  The Empire Builder is notorious for delays, and we’ve certainly seen them before along this route.  We made it home with no issues and enjoyed every minute of our journey.

Takeaways

Overall, we had a wonderful visit to Chicago and train ride home.  Chicago is full of world-class attractions, interesting neighborhoods, and a rich cultural scene.  Chicago’s food scene is a reason to visit alone when you consider the highly rated and varied dining experiences available.  And knowing how easy it is to travel to and from Chicago by rail and to get around this city by using public transportation, there is no excuse for you not to put this at the top of your list of places to visit.

We hope this guide helps you plan your next trip to Chicago and consider a scenic train ride as part of your itinerary.  We know you will love it as much as we did!

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