Here’s how to see Hamilton in Chicago for Cheap and where to dine beforehand! My husband and I procrastinated big time this year in planning for how to celebrate our anniversary. This has become somewhat typical of all areas of our lives, given that we only know John’s travel schedule one month at a time.
The night before our anniversary I said to John: “What if we go see Hamilton in Chicago?” Given that he knows practically every word of the performance and we’ve been dying to see it… he was totally on board!
We looked up last minute ticket and hotel costs. Fortunately for us, flying is free because John is an airline pilot. His job allows our family to fly free on standby. So these tips make it extra affordable, especially for those families who also have access to flight benefits. But you can still find great flight deals to Chicago for reasonable prices last minute. I prefer using Google Flights as a starting point to finding great fares.
We looked up flight loads to see if there was even a good chance to make it to Chicago. A couple of the evening flights both had 50+ open seats. The odds were in our favor! The timing would allow us to drop off our kids to Grandma, go to an appointment, me to get my work done, and still leave us with enough time to grab dinner somewhere in Chicago before the show.
Hotel Accomodations
We opted to stay close to the airport versus downtown because we were truly only in the city to see the show and then fly home the next morning. We found a great $88 rate at Aloft Chicago O’Hare in Rosemont. This price point was great to bring down overall trip costs to see Hamilton. I had to include it in this “how to see Hamilton in Chicago for cheap” guide. We initially thought we might eat at Fogo de Chao next door, and then go ice skating at the Parkway Bank Park Skating Rink across the street.
Unfortunately, we didn’t have enough time to add these things into our agenda this time. But the Rosemont area is such a walkable location–with tons of food options and entertainment nearby (AMC theater close as well). We will have to go back when we have more time to enjoy these other attractions!
Transportation into the City
We walked just under a mile from our hotel to the Rosemont train stop. Usually Aloft and the other area hotels have local shuttles that could just drop you off at the stop. Unfortunately, Aloft’s wasn’t working that night. So we just walked… it was nice! We paid a couple bucks to ride into the city. It’s about 17 stops from Monroe street, which is right where the CIBC Theater is that was showing Hamilton. We still weren’t sure where to eat yet, so we took to Google for some advice.
Where to Eat Before the Show
The Chicago Tribune has a great article with suggestions on where to eat and drink before the show, but we needed something that would be fast. I took to Yelp and found Brightwok Kitchen: “Counter-serve Asian hub offering gluten- and dairy-free stir-fries & salads in bright, modern digs.” Can someone please do us all a favor and franchise this place?
The food was amazing, fresh and fast! The restaurant has 4.5/5 stars on both Google and Yelp and it’s only a couple blocks from the theater. The prices are what you’d expect for a fast-casual dining venue. We got two full entrees and a drink for $23. Eating somewhere simple will bring down your overall trip cost and is a great suggestion in this ‘how to see Hamilton in Chicago for cheap’ guide. I opted for the “Everyday Eat Right” meal and John got a seasonal option: “Fall in Love.”
How to Get Cheap Tickets to Hamilton
This was a learning curve for us. So you can benefit from our mistake (or maybe its not a mistake) and learn how to see Hamilton in Chicago for cheap. We purchased some great looking resale tickets on Ticketmaster the night before the show. At about $150 per ticket, we were so excited to be sitting on main floor, center stage. What we FORGOT to check was the fine print. *OBSTRUCTED VIEW* John had a pillar smack in front of his face.
It was unfortunate, but actually not terrible. He just leaned this way or that way and felt satisfied with the view, especially at the price point we got. So here’s how to get the deal… be willing to go on a weeknight, during a matinee, or pick up an obstructed view seat. Our same seats go for about $325 on a weekend night performance, so I’d say that’s a steal! These ideas, especially weeknights and matinees, will make how to see Hamilton in Chicago for cheap possible.
CIBC Theater Chandelier 
Hamilton Playbills
Don’t forget, you can always enter the Hamilton lottery. This is a great option if you’re flexible and can make travel arrangements last minute, or live within proximity to a show. Just download the Hamilton app and two days before a performance, enter the lottery. The next day they’ll let you know if you win or not. Winning doesn’t mean free tickets, but it does mean 1 or 2 tickets for ONLY $10 a piece! Amazing! This is the ultimate deal for how to see Hamilton in Chicago for cheap (or anywhere for that matter).
We had such a wonderful adventure going to Chicago on a whim. I hope this post helped you learn how to see Hamilton in Chicago for cheap! The performance was captivating and the singing outstanding. Check out my first Vlog for a visual recap of our trip!