From Evansville to Wrigley – How to Plan a Chicago Getaway Without Breaking the Bank

Back in 1998, I spent a couple of days in Chicago. The highlight of that weekend was undoubtedly getting to see my Cubbies play at Wrigley Field. That was nearly 30 years ago, and I still haven't been back - although I've really had the itch to get back up there.

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Just as soon as I allow myself to think about how nice it would be to see Wrigley Field again, my inner accountant chimes in and says, "There's no way you can afford a trip to Chicago!" I just assume he's right, and so I put the thought out of my head. But I continue to wonder how much a quick trip to the Windy City would set me back.

Just for poops and giggles, I turned to SkyNet (aka ChatGPT) and asked it to plan a 2-day trip for two people to Chicago, including tickets to a Chicago Cubs game. I gave it a budget of $1,000. I fully expected to be told I'd need more money for a trip like that. I was pleasantly surprised.

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Turns out you CAN plan a Windy City getaway for less than $1K, and if you ask nicely, that doggone AI will plan just about every aspect of the trip for you. Check out my hypothetical itinerary, with costs, below.

Travel Details

• The drive from Evansville, IN, to Chicago, I,L is a little over 5 hours each way.
• Considering gas mileage and the cost of fuel, the estimated round-trip travel cost is $84.​

Lodging Options

• I was given information about a few affordable Chicago hotels that combine comfort with convenience.
• The estimated cost of a 2-night stay would be between $300 to $350.

Chicago Cubs Game at Wrigley Field

• Game Date: Saturday, July 5, 2025, against the St. Louis Cardinals
• Tickets start at $75.60 each
• Purchasing two tickets at the starting price would total around $151.20.

I was even given a step-by-step breakdown of the trip, including when I should leave, when I should arrive, and what I should do in my spare time.

Day 1

• Morning:
  • Depart Evansville around 8:00 AM
  • Arrive in Chicago by 1:30 PM​
• Afternoon
  • Check into your hotel
  • Explore Navy Pier, a 3,300-foot-long pier on Lake Michigan featuring shops, restaurants, and entertainment options ​Wikipedia
• Evening
  • Enjoy dinner at a local restaurant
  • Consider visiting a jazz club or taking a river walk to experience Chicago's vibrant nightlife​

Day 2

• Morning:
  • Have breakfast at a local café
  • Take a short stroll or visit a nearby attraction​
• Afternoon:
  • Attend the Chicago Cubs vs. St. Louis Cardinals game at Wrigley Field​
• Evening:
  • Dinner at a local eatery
  • Optional: Explore another neighborhood or relax at the hotel​

Day 3

• Morning:
  • Check out of the hotel
  • Begin the drive back to Evansville​

Budget Breakdown

• Fuel (Round Trip) $84
• Lodging (2 Nights) $300 - $350
• Cubs Game Tickets $151.20
• Meals & Miscellaneous $200 - $250
• Total $735 - $835

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This budget leaves room for additional activities, souvenirs, or unexpected expenses while staying within your $1,000 limit.​