Seeing Hamilton in Chicago for Cheap: Part 2 – Flights and Hotel

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Million Mile Secrets team member Jasmin visited Chicago with her 3 kids to see Hamilton – An American Musical.  And she did NOT wait months for tickets or pay a small fortune!

She’ll tell you how she traveled with her family to Chicago using miles, points, and credit card perks for an unforgettable weekend of Big Travel with Small Money!

Jasmin:   Thanks, D!  My children are huge Hamilton fans!  The soundtrack is in heavy rotation in our house, the kids know all the lyrics, and Lin-Manuel Miranda is their hero.

But tickets to the Hamilton productions in New York and Chicago are very hard to get.  Shows are sold out months (or years) in advance, and ticket prices can be incredibly prohibitive.

Seeing Hamilton In Chicago For Cheap Part 2 Flights And Hotel
If You’re an AMEX Platinum Cardholder, You Could Buy Hard-to-Get Hamilton Tickets and Only Pay Face Value

But with a bit of luck and the right credit cards, I was able to surprise the kids with tickets to Hamilton and a trip to Chicago as a Christmas gift – without breaking the bank.  I’ll explain how!

Seeing Hamilton in Chicago for Cheap Index

Southwest Flights Between Buffalo and Chicago (Midway)

Link:   Southwest Rapid Rewards® Premier Credit Card

Link:   Southwest Rapid Rewards® Plus Credit Card

Link:   Southwest Rapid Rewards® Premier Business Credit Card

I used Southwest points to book non-stop flights for the 4 of us between Buffalo and Chicago (Midway).  The flights I chose weren’t the cheapest.  But they worked best for our schedule (after school on Friday to late evening Sunday).

Each round-trip ticket cost 14,834 Southwest points plus ~$11 in taxes.  In total, I spent 59,336 Southwest points and ~$45 in taxes for 4 people.

Note:   The cost in Southwest points is tied to the cash price.  That’s why the points price is rarely a round number!  And there are NO blackout dates!

Everyone gets 2 free checked bags on Southwest, so there was no additional cost.  And we packed snacks and treats in our carry-on luggage in case the kids got hungry.

Seeing Hamilton In Chicago For Cheap Part 2 Flights And Hotel
Safety First! Unless You’re Busy Stuffing Your Face Full of Bright Green Fruit Candy!

I earned most of the points from the Southwest Rapid Rewards® Plus Credit Card.  And while I used to have the Companion Pass, it expired in 2016. 🙁

The kids always get a kick out of the fun announcements on Southwest.  And they’re always sure to read the safety card before we get going.

The flights were just over an hour and were uneventful, except our pilots had to go around on the first approach into Chicago Midway (there was traffic still on the runway).  This excited the kids very much!

On the return journey, our flight home was delayed by ~90 minutes.  By the time we landed at Buffalo, it was 2:00 am!  The kids were exhausted the next day.  But it was well worth it.

Seeing Hamilton In Chicago For Cheap Part 2 Flights And Hotel
Late-Night Delay at Chicago Midway on the Way Home – but the Kids Were SO Exhausted From a Jam-Packed Weekend That They Just Snoozed Until Boarding TIme

We’ve flown Southwest many times and this was the first time we’d experienced a significant delay.  Otherwise, Southwest has always been reliable and we’ve never had trouble getting seats together.

I always check-in online exactly 24 hours prior to departure to get a good boarding position.  When the kids were younger, we were able to board with families after the “A” group, but my youngest is now 7 so they’re too old.  🙁

Getting to the Hotel

It’s easy and convenient to take the Orange Line train from Chicago Midway Airport into downtown Chicago.  Trains run every 3 to 12 minutes depending on the day and time.  And it takes 20 to 25 minutes to get downtown.

Tickets cost ~$2 for adults and ~$1 for children ages 7 to 11.  So the total cost of a one-way ride from the airport to downtown was only ~$6!

Seeing Hamilton In Chicago For Cheap Part 2 Flights And Hotel
Taking the Orange Line Train From Chicago Midway Airport to Downtown Is Easy and Cheap

If you’ll use transit frequently on your Chicago visit, it’s worth purchasing a Ventra card.  It’s like a reloadable debit card with a built-in RFID chip.  To enter the train station, tap your card on the reader and the fare amount will automatically be deducted for your trip.

For children’s fares, you’ll have to get the station attendant to assist you, otherwise you’ll be charged the adult fare.

We took the train to the State / Lake station and walked the rest of the way to the hotel (~15 minutes).  However, we had to make a bit of a detour because of the massive protests happening in the area of the hotel (it was Trump’s inauguration day).

Seeing Hamilton In Chicago For Cheap Part 2 Flights And Hotel
An Unexpected Detour! The Anti-Trump Protesters Were Loud but Generally Peaceful, and There Was a Large Police Presence so We Felt Secure

The kids were wide-eyed at the whole thing.  And it wasn’t the first time we’d encounter protests on this trip!

Hyatt Regency Chicago Exceeded Our Highest Expectations!

Link:   Hyatt Regency Chicago

Link:   The Hyatt Credit Card

1.   How Suite It Is to Get an Upgrade!

We spent 2 nights in a junior suite at the category 4 Hyatt Regency Chicago.  It’s Hyatt’s largest hotel with over 2,000 rooms!  Located right along the river, it has 2 large towers connected by an enclosed bridge.  And it’s walking distance to attractions like Navy Pier and Millenium Park.

For an award night, you’ll normally pay 15,000 Hyatt points.  But instead, I paid $149 plus tax for one of the nights, and used a free category 1 to 4 certificate from the Chase Hyatt card for the 2nd night.

Note:   The Chase Hyatt card is one of the handful of Chase travel cards you CAN still get even if you’ve opened 5+ cards in the past 24 months.
Seeing Hamilton In Chicago For Cheap Part 2 Flights And Hotel
Upgrade! The Kids Enjoyed the Spacious Junior Suite, Which Included a Small Sitting Area and Lots of Room to Run Around

I prefer saving my Hyatt points for more expensive stays.  And because I wanted to use a Diamond Suite Upgrade, one of the nights had to be a cash or points & cash booking.

Technically, you can’t use a Diamond Suite Upgrade on an all-points or anniversary certificate night.  But I asked the reservation agent nicely if it would be possible, and she said the hotel would likely keep us in the suite for both nights.  And they did!

Note:   With the new World of Hyatt loyalty program, Diamond Suite Upgrades NO longer exist.  Instead, Globalist elite members get upgrades to better rooms, up to a standard suite.
Seeing Hamilton In Chicago For Cheap Part 2 Flights And Hotel
Checking out the Bathroom, Which Was Spacious and Fancy! The Kids Loved the Roomy Shower With Glass Enclosure

The staff at the Hyatt impressed me so much.  They’d already put a small fridge and microwave in our suite (which doesn’t normally have these).  And left a kind note letting me know they’d done so because I’d requested these on previous stays.  Incredible customer service!

Seeing Hamilton In Chicago For Cheap Part 2 Flights And Hotel
THIS Is Why Hyatt Is #1 With My Family! The Thoughtful Touches Make All the Difference

The beds were comfortable and, although the suite was more like an oversized regular room, we had loads of space to spread out and make ourselves at home.  My only critique is that the walls are thin – we could hear the folks in the next room talking loudly early in the morning.  But the kids were up anyway… 😉

2.   Decisions!  Chocolate and Wine or Bonus Points at Check-In?

As a Hyatt Diamond member (now “Globalist,” and I didn’t requalify…sniff!), I was offered 1,000 Hyatt points or a food and beverage option as a check-in amenity.  The kids wanted the food and beverage, and I wanted the points, so we compromised and did the food and beverage (but Mommy got to choose the beverage!).

The kids opted for gourmet chocolate truffles and I went for the bottle of wine.

Seeing Hamilton In Chicago For Cheap Part 2 Flights And Hotel
The Hyatt Regency Chicago’s Diamond Amenity Kept the Kids and Mommy Happy!

Unfortunately, my daughter discovered one of the truffles, which had a cream-based filling, had spoiled and tasted like rotten milk!  Yuck!  On our way to the club lounge, I mentioned it to one of the front desk folks so that nobody else would get a nasty truffle.  They were very apologetic.

And we were pleasantly surprised later that evening when room service appeared with the biggest slice of chocolate cake I’ve ever seen, with vanilla Haagen Dazs ice cream on the side.  It took the kids 2 days to finish it!

Seeing Hamilton In Chicago For Cheap Part 2 Flights And Hotel
Way to Go, Hyatt! A Slice of Chocolate Cake the Size of Your Head Makes Everything Better 🙂
Note:   Hyatt has eliminated the check-in amenity with the new World of Hyatt loyalty program.  🙁

It’s personal and genuine service like this that makes Hyatt our favorite hotel chain.  I know Daraius and Emily agree!

3.  Here’s How We Got Unlimited Chicken Fingers, Smoked Salmon, Pastries, & More!

Because I had Diamond elite status, we had access to the Regency Club Lounge.  It was a bit of a pain to get to (on the 35th floor of the tower we weren’t staying in) but it was such a money-saver on this trip!

They serve a substantial breakfast, snacks and drinks during the day, and a light meal with wine, beer, and cocktails (honor bar) in the evening.  We were able to time our meals and snacks so that we only ate out twice during the whole trip!

Seeing Hamilton In Chicago For Cheap Part 2 Flights And Hotel
The Regency Club Lounge Saved Us a Fortune on Meals and Snacks, and the Kids Loved Feeling Like They Were VIPs!

The lounge is warm, well appointed, and was never crowded while we were there.  And the lounge staff were gracious and accommodating, and went the extra mile to find food my picky 7-year-old would eat at dinner! (Cheese sticks, Oreos, and bread!  I promise I give him vitamins!)

Seeing Hamilton In Chicago For Cheap Part 2 Flights And Hotel
The Regency Club Lounge Is Comfy, Modern, and Was Mostly Empty During our Stay

For breakfast, they served fresh fruit, smoked salmon with all the trimmings, and hard boiled eggs…

Seeing Hamilton In Chicago For Cheap Part 2 Flights And Hotel
Plenty of Options for Every Taste! My Daughter Went on a Free-for-All With the Smoked Salmon – “Really? I Can Have as Much as I Want?”
…plus cereal, oatmeal, and all kinds of fresh breads, bagels, and pastries…
Seeing Hamilton In Chicago For Cheap Part 2 Flights And Hotel
Even My Pickypants Little Guy Found Breakfast Items He Would Eat! He Made Short Work of the Pastries and Chocolate Croissants
…and scrambled eggs, yogurt, cheese, juices, and coffee including latte, espresso, and cappuccino.
Seeing Hamilton In Chicago For Cheap Part 2 Flights And Hotel
We Filled up on Breakfast and Saved Lots of Money Instead of Eating Out

In the evening, the lounge serves tasty appetizers, including bread, rolls, veggies, hummus, and antipasti (roasted and marinated vegetables, deli meats, olives, and cheeses)…

Seeing Hamilton In Chicago For Cheap Part 2 Flights And Hotel
You Can Easily Turn the Happy Hour Spread Into a Full Meal for Hungry Kids
…plus, each night, there’s also a hot option.  The first night, they served a kind of Mexican-inspired egg roll.  And the second night, there were (really yummy!) chicken fingers.  Score for the kids!
Seeing Hamilton In Chicago For Cheap Part 2 Flights And Hotel
A Jackpot for the Under-12 Set – Unlimited Chicken Fingers!

We also popped in each day to grab water, soda, fresh fruit, yogurt, and sweets for when we were out and about.

4.   But…NO Pool!

I discovered after I booked the hotel that, despite being the largest Hyatt hotel in the world, they don’t have a pool.

If you’re a parent, you know this is a big deal!  So keep this in mind if you choose to book your family here.

Fortunately, we had so many other activities planned during our short weekend stay that the lack of pool was a non-issue.  Though the kids were a little disappointed.

There’s a very well-equipped gym though.

Seeing Hamilton In Chicago For Cheap Part 2 Flights And Hotel
The Gym Was Empty, and We Didn’t Try the Equipment, but It All Looked Modern, Clean, and Well Maintained

The hotel does provide a list of nearby pools if you need a swimming fix.  But they charge ~$20+ per person, so unless you’re desperate, I’d skip it!

Bottom Line

We spent a total of 59,336 Southwest points and ~$45 in taxes for round-trip flights between Buffalo and Chicago (Midway).  The flights were easy, despite a ~90 minute delay getting home.

Getting to downtown Chicago is cheap on the Orange Line train.  It only cost ~$6 for an adult and 3 kids, and we were within a 15-minute walk of our hotel.

The Hyatt Regency Chicago is in an excellent location, within walking distance of many popular attractions.  Our junior suite was spacious, the Regency Club Lounge was excellent (and saved us a ton of money on food), and the staff were outstanding.

Next, I’ll share our experience seeing Hamilton – An American Musical, and other activities we squeezed in on our quick weekend trip.

Editorial Note: We're the Million Mile Secrets team. And we're proud of our content, opinions and analysis, and of our reader's comments. These haven’t been reviewed, approved or endorsed by any of the airlines, hotels, or credit card issuers which we often write about. And that’s just how we like it! :)

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