Trains, Jousting, and Deep Dish: Our Chicagoland Weekend Getaway

🕒 The Quick Overview

• The Crew: Generational Journeys (The kids, my husband, the grandparents)

• The Destination: Chicagoland & Elgin, Illinois

• Date Stamped: July 2026

• The Duration: ⏱️ 3 Nights / 4 Days

🧾 The Vacation Ledger: Retail vs. Reality

Here is the breakdown of what this trip looked like behind the scenes:

Note: Since the grandparents joined us on this trip, we booked two rooms per night. Since they paid for their own stay, we've excluded their accommodation costs below to keep our household math clear, clean, and accurate to what we spent!

🏨 Accommodations & Basecamp

• DoubleTree by Hilton Chicago - North Shore Conference Center (1 Night) :

  • Retail MSRP: $265

  • What We Paid: $265 (We did take advantage of Hilton promotions and earned a significant stack of points on this stay)

• Holiday Inn & Suites Chicago Northwest - Elgin (2 Nights) :

  • Retail MSRP: $528

  • What We Paid: $100 (Redeemed IHG Free Night Certificates; paid out-of-pocket for taxes & fees)

🚗 Transit & Transportation

• Personal Vehicle / Gas & Tolls:

  • What We Paid: $210

📊 The Final Score:

• Total Retail Value: $1,003

• What We Actually Spent: 🎉 $575

• Total Savings: $428 in our pockets!

🧳 The Transit: The Departure & Log

Instead of trying to squeeze everything into one central downtown stay, we strategically split our accommodations. Starting off on the North Shore put us right where we needed to be for Friday's plans, while moving out to Elgin for nights two and three positioned us just minutes from Saturday's main event in Union. It kept highway driving to a minimum and made the entire weekend feel smooth and easy.

🏨 The Basecamp:

For night one, the DoubleTree by Hilton Chicago - North Shore Conference Center served as the perfect launchpad. The complimentary warm cookies at check-in were an immediate hit with the kids, and the location gave us seamless access to our family lunch.

For nights two and three, we shifted over to the Holiday Inn & Suites Chicago Northwest - Elgin. Redeeming IHG certificates made it an incredible value, but the real win was proximity: being a short, easy drive from the railway museum on Saturday morning meant no rushing, no traffic stress, and a completely relaxed start to our biggest day.

🗺️ The Album: The Trip Highlights

Day 1: Late Drive into Chicago

We didn’t leave for our trip until after our workday was over, so we hit the road, grabbed dinner along the way, and pulled into the hotel late into the evening ready to kick off the weekend.

Day 2: Family Catch-Ups & Medieval Magic

We kicked off our first full day on Friday afternoon by catching up over a cozy lunch with relatives.

After lunch, we took a quick detour to check off a fun pop-culture stop: visiting the iconic Home Alone house! Seeing it in person brought back so much movie nostalgia, and it was the perfect quick pitstop to stretch our legs.

For dinner, we dialed up the entertainment with a trip to Medieval Times. The kids were completely hooked by the jousting, the horses, and the high-energy crowd. Eating dinner with our hands while cheering on our knight was the absolute highlight of the night!

Day 3: Train Dreams & Deep Dish Delights

Saturday was the centerpiece of the entire weekend: Day Out with Thomas at the Illinois Railway Museum!

I wasn’t entirely sure what to expect going in, but the event was remarkably well-organized and smooth from start to finish. The kids were truly on cloud nine getting to ride full-sized versions of both Thomas and Percy, alongside exploring tons of interactive, train-themed activities across the grounds. Seeing their faces light up as Thomas pulled into the station made every single mile driven completely worth it.

We wrapped up the big day by tracking down a classic Chicago staple: deep dish pizza. A piping hot pie was secured, making the evening a total win for the grown-ups, too!

Day 4: A Relaxed Morning & Easy Drive Home

After a busy two days, we took Sunday morning completely slow. We hit the road for an easy, seamless drive home—already talking about our favorite train memories on the way back!