Brewtripping Chicago: The Deals

I don’t know about you, but I have a long bucket list. Every year I seem to add more items to the list than I cross off, and although some of the things are bigger than others, I’m generally hampered by two main obstacles: time and money.

In the travelling category, the city that has been on my list for the longest is Chicago. Why, you ask? Is it the architecture? The history? The hotdogs? Well, yes, all of those. But really, my interest in Chicago goes way back, starting with a TV show called “Perfect Strangers“. There are plenty of shows and movies set in Chicago — “Family Matters”, “Married with Children”, practically every John Hughes movie — but for me, “Perfect Strangers” is the show that started it all.

The problem with getting to Chicago was the money. Travelling is the best, but an empty bank account? Not so much.

This is where we got lucky. A flight credit meant that our way there was covered, and a sale at the Millennium Knickerbocker Hotel gave us a great place to stay. Brewtripping on a budget had begun!

Free Things to do in Chicago

One of the things we loved about Chicago was the amount of stuff we could do for free. Let’s face it: We’re cheap. So any way to explore and have fun without spending a dime is just our style. Part of brewtripping is using beer as a way to explore new cities, so the focus is on the beer and the city, not the other expensive sites that would otherwise draw us there. We found quite a few free and almost-free things to do on our explorcation and could probably have spent the whole trip doing just those!

Old and new architecture along the Chicago River
First and foremost is the architecture. Chicago is a skyscraper city and the diversity of its landscape, historic buildings and new towers offers a photo opportunity at every turn. And what amazing buildings: From the famous John Hancock Center and Willis (Sears) Tower (America’s tallest!) to the shiny and overbearing Trump Tower, there was enough to see downtown alone to last the entire trip.

Public space, too, was full of free adventures! The walkway that follows Lake Michigan north of Navy Pier, as well as the Riverwalk along the Chicago River, let us enjoy several leisurely hours of siteseeing for absolutely no cost. Millennium Park gave us a great morning of taking photos at the giant bean (called Cloud Gate) as well as Buckingham Fountain (no connection to Buckingham Palace, apparently – who knew!), which you might recognize from the opening credits of “Married With Children“!

Cloud Gate in Millennium Park
Cloud Gate in Millennium Park
Navy Pier is Chicago’s most-visited attraction, and although we couldn’t really understand why, it was free. We did see a bunch of guys in speedos riding Segways, so that was… interesting.

Aside from that, we got to check out Soldier Field (and just missed a One Direction concert – oh darn), took photos of a ton of statues, including Christopher Columbus and Copernicus, strolled by lovely public beaches (people were actually swimming in Lake Michigan, which I think is gross), and even caught free pilates classes back in Millennium Park. There was even a free movie under the stars – if we’d only known!

The best part about all this site seeing? It was all within walking distance of the hotel! You can go to Chicago, spend hours and days exploring, and not spend a cent. Now that’s a cheap adventure!

The Nearly Free and Great Deals

Architecture and free photo ops are amazing. But if I had come back home from Chicago saying that all we did was walk around taking pictures, I would be ashamed, not because we didn’t see a lot, but because we were in a city with some of the country’s biggest and best museums, the tallest buildings, and most nerdy boat tours. And who can say  no to those?

The problem with museums and tours is that they can be expensive. Once you add up the fees for admission and special exhibits, your wallet can go from nearly empty to completely sad, and you’ll be forced to eat free Costco samples for lunch! Not that we’ve ever done that.

But what if I told you there’s a way to see all these things for free? Chicago, like most major cities, has something called a City Pass, which is essentially a coupon book you pay one fee for and which gets you into a number of top sites. Usually these passes are around $100, which saves a lot off normal admission and also gives you “fast pass” (i.e., front-of-the-line) entry. That alone is a great deal!

The Art Institute of Chicago
The Art Institute of Chicago
Still. $100? This is Brewtrippers, not Cashtrippers. I’ll let you in on a secret: If you collect Air Miles and have a few hundred to spend, you can redeem your Miles for a free City Pass! I had enough Air Miles for two passes, so for absolutely no fee, we got admission to the Art Institute of Chicago (home of American Gothic, Van Gogh’s self portrait, and a famous scene from Ferris Bueller), the Field Museum (home of Sue, the most complete T-Rex uncovered to date, as well as Night at the Museum), and the Willis Tower and John Hancock Center, where we rode super-fast elevators to the 103rd and 94th floors respectively. The City Pass also gave us admission to the Shedd Aquarium and Adler Planetarium, but time just wasn’t on our side. Next time!

All of these tourist and cultural sites? Free! Just cost a few Air Miles.

A view of the skyline from the Chicago River
Also in the category of nearly free is the previously-mentioned nerdy boat cruise. Chicago has a ton of them, and I knew we had to do one. Boat? Free coffee and cookies? History lesson? Sign me up! Our deal this time came in the form of a Groupon which we bought before the trip. Shoreline Tours gave a great architectural tour which included both Lake Michigan and the Chicago River, and of all the tours we looked at, it had the best deal.

So, the lesson here? Before you travel anywhere, check ahead of time for Groupons, Air Miles deals, special discounts, and free events. It’s the best way to save your money and turn your trip into a fun- and memory-filled holiday that you’ll never forget! We were able to cross off some big bucket list items (including seeing a Cubs game at Wrigley Field!) and barely spent a cent. And you can too!


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