If you’re planning a Chicago trip with your family and you want maximum fun with minimal planning stress, this is the exact setup we used: Hyatt Regency Chicago (Wacker Dr.) + a 2-day Go City Pass.
Outcome you’re getting from this post: you’ll know where we stayed, what we did in 2 days, what the pass covered, what surprised us, and what to watch out for. So you can plan your trip without the guesswork.
This post is not sponsored, and the Go City Pass link is not an affiliate link. Everything shared here is based on my personal experience and opinions from our trip. Prices and availability can change. Always double-check details before booking.
Pick your trip in 15 seconds
- Want walkable downtown vibes + easy access to tourist highlights → stay in The Loop / Riverwalk area (we did)
- Want paid-once-and-go exploring → grab the Go City pass for your busiest days
- Want the easiest family flow → do one museum + one “fun” activity per day (keeps everyone happy)
Reflective question #1: Are you trying to see everything, or are you trying to enjoy the day without rushing the kids?
Quick budget snapshot (what we paid)
- Hotel: about $500 total for 3 nights (prices vary by dates—ours was a win!)
- Go City Pass: $130 (covered all the activities below)
What we included on the pass (with “up to” individual prices):
- Hop-On Hop-Off Big Bus Chicago (up to $58)
- Field Museum (up to $43)
- Shedd Aquarium (up to $49)
- Museum of Illusions Chicago (up to $42)
- Seadog Lakefront Speedboat Tour (up to $49)
Big math: those “up to” prices add up to $241 worth of activities vs $130 for the pass → about $111 saved (per person, before any taxes/fees).
🏨 The Hotel Experience
We stayed at Hyatt Regency Chicago, 151 E Wacker Drive and it was honestly gorgeous.
The only thing missing was a balcony (because baby… imagine those views), but the room itself was spacious with plenty of chairs to chill. I brought my laptop for content and the desk setup understood the assignment.
Signature detail: the lobby/bar area gets this color-changing glow at night, and with the city lights outside? It’s giving main character energy. (Also… the drinks were good, so plan accordingly 😂.) Hyatt also lists multiple on-site dining/bar options, which made it easy when we were tired-tired.
Hotel watch-outs (keep it real):
- No balcony (if that’s your non-negotiable, note it up front)
- The gym was a bit of a walk from our room (not a dealbreaker, just a heads-up)
🗺️ Exploring Chicago with GoCity Pass
The Go City pass was the BEST move for seeing highlights without paying separately for everything. Go City offers an All-Inclusive Pass where you can visit as many included attractions as you want for the number of days you choose.
Go City watch-outs (read this so you don’t get played):
- Some attractions require reservations in the Go City app—check the guidebook before you head out.
- Pass “days” are calendar days, and they’re used on consecutive days (not a rolling 24-hour clock).
Reflective question #2: Are you a “let’s do EVERYTHING” traveler… or a “one or two big things + vibes + rest” traveler?
🏛️ What We Did in Chicago (2 Days, No Stress, Just Vibes)
Day 1: City views + laughs + adrenaline
This day felt like the perfect “Chicago intro.” We started with the Hop-On Hop-Off bus so we could get our bearings without wearing ourselves out, then we did something playful (Museum of Illusions) and ended with something that made us feel like we were really outside (Seadog speedboat).
🪞 Museum of Illusions Chicago (the most fun kind of chaotic)
This stop was pure laughter. The museum is interactive, so it doesn’t feel like you’re quietly walking around reading plaques—this is “babe, take my picture again” energy. You’re bouncing from room to room like a kid, and honestly, it’s a great break from “serious sightseeing.”
That Vortex Tunnel is the star. It plays with your balance so hard that you think you’re walking straight, but your body is like “girl, no you’re not.” Holding the rails is not optional 😂. The Reversed Room is another favorite because it makes the photos look wild—like you’re walking on walls or hanging from the ceiling. Museum of Illusions Chicago
What made it better: we didn’t try to rush through it. We gave ourselves permission to play and be silly.
Big sis tip: Wear something you feel cute in—this is a photo-heavy stop, and the pics come out so good when you’re in your element.
If you’re with kids: this is a guaranteed win because it feels like an activity, not a “museum museum.”
🚤 Seadog Lakefront Speedboat Tour (thrill + skyline + “hold onto your lashes”)
Okay … this was the moment where Chicago said, “So y’all thought you were just gonna look cute?” 😭 The speedboat is exciting and the skyline views are gorgeous, but the wind and water spray are doing the MOST. I’m laughing, trying to stay in the moment, and also trying to protect my braids and whatever lashes were still hanging on.
What I loved is that it’s not just a fast ride. The guide is talking, pointing things out, and giving skyline stories while you’re out on Lake Michigan with the city right there looking expensive. The guide even pointed out that light-blue, super pretty tower—the St. Regis Chicago—and shared that it was designed by Jeanne Gang of Studio Gang (Chicago’s first female architect you mentioned).
What made it better: leaning into it instead of fighting it. Once you accept you might get sprayed a little, it becomes pure fun.
Big sis tip: bring a light jacket (even in May), and don’t wear anything you’ll be mad about if it gets misted. This tour is literally described as a high-speed lakefront ride with skyline storytelling—so expect wind + splash.
Night recap (because this mattered)
After a day like that, coming back to the hotel and having a good bar downstairs is everything. You said you loved the hotel bar, and that makes such a difference—because sometimes you don’t want to “go out,” you just want a cute drink, good vibes, and an easy night. (And yes… the night gets more magical until the drinks start kicking in 😂)
And the deep dish? The fact that it was great is important because deep dish can be hit or miss depending on what people like—but when it hits, it HITS.
Day 2: Aquarium day + explore-and-vibe day
Day 2 felt softer. More “take our time, enjoy the city, pick little moments,” which is exactly how you balance a trip so you don’t go home exhausted.
🐠 Shedd Aquarium (calm, mesmerizing, and worth the time)
The aquarium was one of those experiences that makes you slow down without even trying. It’s cool inside, the lighting is calming, and everybody gets quiet for a second because you’re watching these animals move so smoothly.
That feeding moment you mentioned (whether it was dolphins or whales) was the kind of thing where you forget you’re even recording because you’re locked in. And of course, the penguins are always going to do what needs to be done: cute, funny, and impossible not to watch.
What made it better: treating it like a main activity, not a quick stop. You could breeze through, but it’s way better when you give it time.
Tip: plan at least 2–3 hours if you want it to feel enjoyable and not rushed.
🚍 Hop-On Hop-Off + exploring (the “we outside, but peacefully” part)
Riding the bus again on Day 2 was smart because it let you explore without overplanning. It’s the perfect setup for “let’s hop off here, walk a bit, then hop back on when we’re tired.” That flexibility is what keeps the trip fun instead of stressful.
What made it better: not forcing an overly packed schedule. Exploring the city like this gives you space for random little wins—cute photo moments, a chill walk, and discovering areas you didn’t plan for.
🚍 Hop-On Hop-Off Big Bus (our “let’s learn the city” move)
Starting with the bus made the whole trip easier because Chicago is BIG-big, and this gave us a “mental map” fast. Sitting up there, watching the city move around us, it felt like we were sightseeing without having to think too hard. The bus also helped us spot little areas we wanted to come back to—like, “Okayyyy, put a pin in that.”
What made it better: we weren’t rushing. We let ourselves ride, listen, and just take it in.
Big sis tip: Do this early in the trip so you’re not spending the rest of your days like “wait… where are we?”
If you’re filming content: this is an easy way to capture quick skyline clips, street energy, and “POV: first day in Chicago” moments.
💡 Final Thoughts
Chicago was the perfect blend of adventure, relaxation, and learning. The GoCity Pass was worth every penny, the Hyatt Regency made us feel at home, and the city’s energy was unmatched. I’m so grateful we experienced it together—and can’t wait to share more tips from our travels. Stay tuned, besties! ✨