Getting there

Chicago is extremely accessible. Since it’s such a huge commerce center, you can travel there by plane, train, or bus!

Megabus: Theoretically you can get to Chicago for $2.50 a person if planned well enough in advance. Megabus has direct routes from 14 cities including Omaha and Toledo. These are typically double decker buses with Wi-Fi and outlets at your seat. We've traveled on Megabus many times.

Flights: We haven’t paid full price for a flight in 2 years. And neither do you. We flew Southwest completely on points earned from credit card bonuses. If you are brand new to using miles to fly free I recommend buying Frequent Flyer Master by Chris Guillebeau for 49 bucks. Best money I ever spend, this guy got me traveling more. This year he will complete his goal of traveling to every country in the world. He knows how to work the miles and points.
Frequent Flyer Master
If you have some experience getting credit card bonuses and working mile promotions, I recommend adding the blogs “Mommy Points” and “Million Mile Secrets” to your daily reading. If flying to Chicago, then flying for free is one of the greatest ways to save money on your cheap Chicago vacation. 

Train: Amtrak often has sales. Set up a Amtrak Guest Rewards account. If you travel within the 1st 90 days you get a 500 point bonus. Amtrak also frequently has credit card offers with 32,000 point bonuses for their Guest Rewards program. That's enough for 10 roundtrip tickets from St Louis to Chicago! Free!

Once in Chicago
If you want to keep that Chicago vacation a cheap Chicago vacation, don’t rent a car. Both airports - Midway and O’Hare - have metros with downtown access. The fare is $2.25 from either airport to any point in Chicago. Oh, and credit cards are accepted.

Chicago’s public transit system connects to all parts of the city. However, staying downtown certainly reduces your transit costs. We didn’t use the metro once we got downtown.