This post is a guest contribution from one of our incredible BoldlyGo community members, Rosie Calig (@Rosie Calig). If Rosie’s name sounds familiar, it’s because this is her second contribution to the BoldlyGo community. After previously sharing her family’s stay at the Waldorf Astoria Costa Rica, she’s back with another points-and-miles success story. This time, Rosie shares how she and her family used IHG Free Night Certificates for a fun-filled family weekend in Chicago, proving that memorable trips don’t always require long flights or luxury resorts. We love showcasing real stories from within our community because some of the best travel strategies come from people actually putting them into action. If you’d like to share your own experience or points-and-miles win with the BoldlyGo community, you can submit your contribution here.

Weekend at a Glance

Why Chicago Is Great for Families

If you’re sitting on IHG Free Night Certificates and haven’t thought about Chicago yet, this post is for you.

Chicago is one of those cities that just works for families. It’s walkable, there is no shortage of things to do with little ones, and it’s incredibly easy to get to from anywhere in the Midwest. We drove from Columbus, which took about 5.5 hours, but there are also plenty of affordable nonstop flights from cities all over the United States.

Between the parks, museums, shopping, restaurants, and family-friendly attractions, you can easily fill a long weekend without ever running out of things to do.

For us, it was the perfect destination for a quick family getaway.

The Booking Strategy

We stacked two IHG Free Night Certificates, one on my account and one on my husband’s account, and topped off the reservation with 3,000 IHG points to cover a Friday-to-Sunday stay at the InterContinental Chicago.

We used one IHG Free Night Certificate (FNC) on my account and a second on my partner’s account, then emailed the hotel directly to request that we stay in the same room for both nights.

The hotel was accommodating, though you’ll likely need to stop by the front desk once during your stay to reactivate your room key when the second reservation takes effect. It was a minor inconvenience and completely manageable.

We stayed in a 2 Double Classic Premier City View room and did not receive an upgrade at check-in. I emailed before arrival and also asked at check-in, but no luck. The room felt a little tight for a family of three, though it was perfectly adequate for a weekend stay.

As Platinum Elite members, we received 600 welcome amenity points each. We didn’t receive any additional perks, room gifts, or upgrades, which was generally in line with our expectations.

InterContinental Chicago Review

What We Loved

• Iconic historic property
• Beautiful indoor pool area
• Excellent location near the Magnificent Mile
• Great use of two IHG Free Night Certificates
• Easy access to restaurants, shopping, and attractions

What We Didn’t Love

• Elevators were painfully slow
• Wait times could reach 15 to 20 minutes during peak periods
• Valet retrieval was extremely slow
• Rooms felt somewhat small for families

Our Honest Verdict

Would we go back?

Probably not.

There are simply too many excellent points hotel options in Chicago, and the elevator situation genuinely left a sour note on an otherwise fantastic weekend.

That said, we were barely in the room, and the city itself made the trip worthwhile.

A Quick Note About the Pool

The pool is absolutely stunning and one of the highlights of the property.

However, it’s surprisingly deep.

If you’re traveling with young children, bring floaties. Seriously. For us, they were non-negotiable.

Getting Around Chicago with a Toddler

Once we arrived, we never touched our car again.

We walked almost everywhere and used Uber when needed. Given how long valet retrieval took, leaving the car parked all weekend was definitely the right move.

One question we get frequently is about car seats while traveling.

We personally use the Hiccapop inflatable car seat for Uber rides. Of course, always verify current safety recommendations based on your child’s age and weight, but for us it worked perfectly and made ridesharing with a toddler much easier.

Our Chicago Family Weekend Itinerary

Friday

After checking into the hotel, we headed straight to the pool.

It was the perfect way to start the weekend and let our daughter burn off some energy after the drive.

Dinner: Pizza Parlor Bar River North

This place had more of a bar atmosphere than we expected, but it turned out to be surprisingly kid-friendly.

We sat outside, which gave our daughter plenty of room to dance around while we enjoyed dinner. After a long travel day, it was exactly what we needed.

Saturday

Brunch: La Catedral Café & Restaurant

If you only take one restaurant recommendation from this post, let it be this one.

The food was excellent, the location was convenient, and the atmosphere was great for families.

Highly recommend.

And whatever you do, order the Café de Olla.

Maggie Daley Park

After brunch, we crossed the street and walked directly to Maggie Daley Park.

Honestly, this place feels magical if you’re traveling with kids.

There are climbing structures, slides, playgrounds, and activities for nearly every age group. You could easily spend several hours here without anyone getting bored.

We eventually used Uber credits to get back to the hotel because little legs were officially done for the day.

Lunch

Chick-fil-A, located conveniently across from our hotel.

Sometimes easy is the right choice.

Slime Museum

The question I always get is:

“Is it worth it?”

Honestly… probably not.

But we still had a blast.

Kids get to create slime and take it home, which is a huge win if you’re traveling with toddlers.

My biggest recommendation is to slow down and explore each section rather than rushing through. The experience moves quickly, and it’s easy to miss things if you’re trying to keep up with an energetic little one.

Dinner: Volare

Volare was probably our nicest meal of the weekend.

The food and service were excellent, but it never felt stuffy or overly formal.

We sat outside, which worked perfectly with our toddler.

Evening Activities

We stopped by the American Girl Store before taking a stroll down the Magnificent Mile.

A quick tip for parents:

If you want the American Girl experience without spending hundreds of dollars, head straight to the baby doll section.

Our daughter was completely in heaven and barely glanced at the larger dolls.

Sunday

We originally planned to visit Lincoln Park Zoo.

If you’ve never been, admission is free and it’s one of the best family-friendly attractions in Chicago.

Unfortunately, our daughter wasn’t feeling well, so we decided to head home earlier than planned.

Lincoln Park Zoo is definitely at the top of our list for next time.

Best Things We Did with a Toddler

If you’re visiting Chicago with young children, these were our favorite experiences:

1. Maggie Daley Park
2. Hotel Pool
3. Slime Museum
4. American Girl Store
5. Walking the Magnificent Mile
6. Lincoln Park Zoo (planned, but highly recommended)

Would We Stay at the InterContinental Chicago Again?

The answer is probably no.

The hotel’s location is fantastic, and the pool is beautiful, but the elevator delays and valet issues significantly impacted the overall experience.

That doesn’t mean we regret the redemption.

Using two IHG Free Night Certificates for a property like the InterContinental Chicago is still a very solid use of those certificates.

We simply think we’d try another points hotel next time.

Final Thoughts

Chicago is an amazing family destination.

It’s walkable, packed with activities, easy to reach, and offers something for every age group.

Using two IHG Free Night Certificates back-to-back at the InterContinental Chicago proved to be a smart redemption strategy, even with the minor inconvenience of the key card swap between reservations.

While we didn’t maximize the hotel experience itself, Chicago more than made up for it.

Between the parks, restaurants, shopping, and family-friendly attractions, we left already talking about our next visit.

And honestly, that’s probably the best review a destination can get.

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