How My Daughters and I Spent Three Days in Chicago for Free

Chicago is my favorite U.S city. I've traveled there 20+ times for work and since my two daughters have heard so much about it, they've always wanted to go too. When we were planning our recent trip to Thailand and Cambodia, I wanted to find a way to work Chicago into our itinerary. 

I had specifically picked out flights that went through Chicago so that we could build in a stopover, but those flights would only give us half a day outside of the airport on each leg of the trip. By making two small changes to our flight plans we were able to spend two nights and three days in Chicago and still ended up saving money on the overall trip.

1. Booked our international flights in and out of Chicago. 

Flying in and out of a major airport hub is typically more affordable than flying out of a medium or smaller sized airport. I booked roundtrip flights from Birmingham (our home) to Chicago on Southwest Airlines and then booked our international flights in and out of Chicago. This change alone saved over $600 between the three of us which funded two hotel nights plus all transportation and food in Chicago. 

2. Explored all flight time options.

Instead of the convenient and affordable flight that I had originally picked out, there was a 4:00am return flight from Bangkok that would save another $1,200 between our three tickets. The flight would involve 18 hours in the air regardless, so why not add to that by heading to the airport at 1:00am? In hindsight, I think this actually worked in our favor to get back on U.S. schedules faster.

By making these two easy changes to our travel plan, we funded three days in Chicago and still saved money on our overall trip. Effective travel planning is a lot like a puzzle. It takes time and research to find the right pieces for your budget and goals, but when you finally have everything in place, you're left with beautiful memories that will last forever.