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- In Chicago, our family enjoyed world-class entertainment that didn’t drain our bank account.
- Our tickets to comedy shows at the famous Second City and NBA and NHL games were affordable.
- Chicago’s free attractions, like the zoo, were worthwhile — not just time fillers to save costs.
Taking teenagers on vacation can be expensive, but Chicago flipped the script on our expectations.
With four 18-year-olds in tow, my wife and I headed from Australia to the Windy City this past winter.
Much to our delight, we discovered a major city that consistently delivered premium experiences without the premium price tag.
Here are some of the highlights.
We scored last-minute tickets to pro games without breaking the bank.
Attending live sporting events can destroy a vacation budget, but Chicago offered us a pleasant surprise. On our trip, we secured last-minute seats to NHL Blackhawks and NBA Bulls games for under $50 per ticket.
Despite being seated in the upper level, we had clear views of each game. The stadium’s atmosphere felt electric, and the excitement was infectious during each visit.
Both teams delivered victories and treated crowd members to free hot dogs and cookies — making the wins even sweeter for our budget-conscious group.
It was amazing to witness comedy gold for only $39 a ticket.
The Second City is a legendary comedy institution in Chicago where many famous comedians and actors got their start.
Having performed improv in college and studied Second City’s techniques, I knew its reputation well. However, I worried live comedy might bore the kids, who are more used to scrolling through minute-long jokes on TikTok.
However, for just $39 a ticket — less than nosebleed seats on Broadway — I was willing to take my chances. We ended up securing spots a few rows from the stage, and my concerns evaporated when the first sketch began.
A scene about an overenthusiastic dad constantly interrupting his teenager had them laughing so hard — they said it was a perfect parody of me!
Watching tomorrow’s comedy stars perform where legends like Bill Murray and Tina Fey started their careers made the experience even more remarkable.
The kids even asked to see another show before we left Chicago.
The city’s free activities were actually worth our time.
Chicago offers legitimate value with its free attractions, which isn’t always the case in big cities.
Ice skating at the seasonal Maggie Daley Park Skating Ribbon only cost us skate rental fees, and we enjoyed gliding past an Instagram-worthy backdrop of the Chicago skyline.
The Chicago Fed Money Museum was also a fascinating free detour, complete with a souvenir bag of shredded currency worth $342 — sadly unusable but a unique memento.
Lincoln Park Zoo, unlike many zoos in major cities, charges no admission — and it’s impressive, with 35 acres housing hundreds of animals.
Plus, the city’s architectural treasures proved to be unexpectedly engaging.
Chicago is renowned for its architecture, and we didn’t have to pay for tours to enjoy it.
Our phones were constantly out to capture marvels like the massive stained-glass Tiffany dome at the Chicago Cultural Center and the ornate building lobbies downtown.
Even the grand staircase at the Harold Washington Library became a photo spot.
Public transport made splitting up easy and affordable.
Although rideshare costs in major cities can quickly add up, Chicago’s efficient public-transportation system kept our travel budget in check.
Our rental in Little Italy’s proximity to an “L” train stop meant downtown attractions were just minutes away — and a $20 weekly transit pass became a key to the city for each of us.
We found the straightforward transit maps and schedules to be easy to follow, which gave the teenagers unprecedented independence and more chances for fun.
They confidently explored Michigan Avenue while my wife and I grabbed coffee. One morning, they enjoyed sleeping in while we started our day early.
This freedom to occasionally split up made the trip more enjoyable for everyone.
Chicago shattered our assumptions about travel costs in big cities.
Before our trip, I was especially worried it’d be tricky to find after-dinner entertainment for 18-year-old Aussies who can drink legally at home but not in the US.
Instead, Chicago’s nighttime energy created perfect shared experiences that didn’t break the bank.
Whether cheering at a Bulls game or laughing together at Second City, everyone felt part of the city’s vibrant evening scene — and my wife and I could enjoy a cocktail without making it the focal point.
I was so pleasantly surprised that a metropolis boasting world-class architecture, professional sports, and groundbreaking comedy delivered such experiences without inflating our credit-card statements.
Although visiting big cities always comes at a cost, Chicago’s value meant we spent more time experiencing attractions and less worrying about expenses.
