Getting There: The Scenic Amtrak Journey to Chicago
Our trip to Chicago began in the most relaxing way possible—aboard an Amtrak train. If you’re considering a visit to the Windy City, we highly recommend this scenic and stress-free mode of transportation. There’s something nostalgic about watching the landscape roll by as you sit in comfort. With spacious seating and the freedom to move around, it felt far more enjoyable than flying or driving.
We appreciated being able to pack what we needed without worrying about security hassles. The onboard amenities were more than enough for us to unwind, and the smooth ride allowed us to relax and chat about all the exciting things we had planned. Amtrak made the journey itself a highlight of our vacation!
Cozy Stay at the Holiday Inn Express on 640 N. Wabash
After arriving in Chicago, we checked into the Holiday Inn Express on 640 N. Wabash. The location was perfect—right in the heart of the city. Though our room was on the smaller side, it was clean and had everything we needed for a comfortable stay. The best part? The free breakfast. Each morning, we enjoyed a variety of options that fueled our busy days ahead.
If you’re looking for a budget-friendly yet convenient place to stay in downtown Chicago, this Holiday Inn Express fits the bill. The hotel staff was helpful, and being just minutes away from major attractions made it easy to explore the city.
Navigating the City with Lyft and Uber
Getting around Chicago was a breeze thanks to ride-sharing services like Lyft and Uber. We quickly found that Lyft was generally cheaper than Uber, and we took full advantage of that by signing up for email deals that saved us even more money. Our first ride with Lyft came with a discount, and each ride afterward was reasonably priced.
The drivers we encountered were friendly and professional, making us feel safe and comfortable as we moved through the bustling streets of the city. When comparing Lyft and Uber, Lyft consistently offered better rates, and it became our go-to for the trip. Whether it was a quick ride to Navy Pier or a journey up the Magnificent Mile, Lyft made it affordable and easy.
Exploring the Iconic Magnificent Mile
One of our first stops was Chicago’s famous Magnificent Mile. This bustling street is lined with high-end shops, historic buildings, and a variety of restaurants. Whether you’re a shopaholic or just love the energy of a big city (which is amazing), this stretch is a must-see. We found ourselves walking up and down, marveling at the architecture and the vibrant atmosphere.
We always felt safe while exploring the Magnificent Mile, thanks to the visible police presence. It was comforting to know that the area was well-patrolled, allowing us to fully enjoy the experience without worry. From luxury stores to charming coffee shops, it’s easy to see why this street is so iconic.
Experiencing the Chicago Skyline at the John Hancock Center
The John Hancock Center, now known as 360 CHICAGO, is one of the best places to take in the city’s breathtaking skyline. The observation deck is located on the 94th floor, offering incredible panoramic views from 1,030 feet above the Magnificent Mile.
One of the most exciting features is the high-speed elevator, which takes you from the ground to the top in just 40 seconds. The speed of this elevator ride alone is a thrill, giving you a sense of how massive and impressive the building is.
A unique attraction at the John Hancock Center is TILT, a special window that literally tilts you outward over the city. This glass-enclosed platform allows you to lean forward at a 30-degree angle as you face the streets below, providing a heart-pounding experience like no other. It’s the highest thrill ride in Chicago and perfect for those who want an extra adrenaline rush along with their view!
A Trip Back in Time: Medieval Times Dinner and Tournament
One of the highlights of our trip was stepping back into the Middle Ages at Medieval Times Dinner and Tournament. We’d heard great things about the show, and it did not disappoint. The grand spectacle of knights in armor, horses galloping through the arena, and an engaging storyline had us on the edge of our seats.
The dinner was equally enjoyable—served in true medieval fashion without utensils, which added to the authenticity. We dug into a hearty meal while cheering for our favorite knight. It was fun, lively, and a perfect way to spend an evening in Chicago. Whether you’re a history buff or just enjoy a good performance, Medieval Times is a fantastic experience.
Sampling Chicago’s Famous Food: Portillo’s & Barnelli’s
You can’t leave Chicago without trying a Chicago-style hot dog, and for us, the best spot to do that was Portillo’s & Barnelli’s. We were excited to dive into this local favorite, and it truly lived up to the hype. A classic Chicago Dog comes with mustard, relish, onions, tomatoes, pickles, sport peppers, and a dash of celery salt—all packed into a poppy seed bun. The combination of flavors was unlike any hot dog we’d ever tried.
Portillo’s had a vibrant, casual atmosphere, making it the perfect place for a quick bite between sightseeing stops. If you’re in Chicago, do yourself a favor and grab a hot dog from Portillo’s. You won’t regret it!
Fun and Games at Top Golf
For a change of pace, we spent an evening at Top Golf, where we got to combine fun with a little friendly competition. We played both the standard Top Golf game and the Angry Birds game, which added a fun twist to the experience. Whether you’re a pro golfer or a beginner, Top Golf offers something for everyone.
The lively atmosphere and interactive games kept us entertained for hours. It’s a great spot for couples or groups looking for a fun way to unwind after a day of sightseeing. Plus, the food and drinks were fantastic, making it a complete entertainment package.
A Close-Up with The Bean: Chicago’s Millennium Park Highlight
Another must-see on our list was The Bean (officially known as “Cloud Gate”) at Millennium Park. This massive, reflective sculpture is one of Chicago’s most photographed landmarks, and it’s easy to see why. The Bean’s shiny, mirrored surface offers a fun and unique photo opportunity, as it reflects the city skyline and the people around it in unexpected ways.
We spent some time admiring the art piece and, of course, snapping a few photos. Whether you’re a casual visitor or an art enthusiast, The Bean is a playful, interactive experience that adds a touch of whimsy to any visit to Chicago. Plus, Millennium Park itself is a beautiful place to stroll, with lush greenery and other interesting art installations.
Spotting the “Adventures in Babysitting” Building from Afar
As fans of the 80s classic Adventures in Babysitting, we were excited to catch a glimpse of the iconic skyscraper from the film. While we didn’t get up close, seeing the building from a distance was still a fun nod to the movie. The building, officially known as **One Prudential Plaza**, is located in downtown Chicago and plays a key role in one of the most memorable scenes of the film.
In the movie, the characters climb the building’s exterior during a high-stakes escape, creating a thrilling moment as they dangle from the side. Standing there, looking at this towering structure, we couldn’t help but picture that nail-biting scene! For movie buffs, spotting this landmark is a cool way to relive some 80s nostalgia while exploring the city.
Chicago’s Balance of Modern Fun and Historic Charm
Chicago is a city that truly offers the best of both worlds. From the modern, sleek design of the skyscrapers to the historic charm of its neighborhoods, there’s something here for everyone. Whether you’re into art, architecture, food, or entertainment, Chicago has a way of pulling you in with its vibrant culture and rich history.
Our trip was a perfect balance of thrills, relaxation, and discovery. From high-energy activities like Top Golf and the John Hancock Center’s TILT ride to peaceful walks around Navy Pier and Millennium Park, we left Chicago with a sense of having experienced all its layers. It’s a city that we’ll definitely visit again.
Conclusion
Our trip to Chicago was nothing short of amazing. From the scenic Amtrak ride to the thrilling views from the John Hancock Center, every moment was memorable. Whether it was indulging in Chicago’s famous food, exploring its landmarks, or enjoying casual fun at Top Golf, there was never a dull moment. With friendly locals, a vibrant atmosphere, and an endless list of things to do, Chicago is a city that will keep you coming back for more.
Check out more of our travel adventures in our other travel blogs. Find itinerary based on this trip on our itinerary page.
#ChicagoTravel #WindyCity #ExploreChicago #ChicagoSkyline #JohnHancockCenter #MedievalTimes #ChicagoDog #Portillos #NavyPier #TopGolf #AdventuresInBabysitting #MillenniumPark #TheBean #AmtrakAdventures #LyftChicago #TravelTips #CityExploration #TravelInspiration #Lyft
