Chicago Great Vacation Trip for Baby Boomers

The debate was on. My husband and I were planning a trip for our 38th anniversary and we had two free domestic airline tickets. Where would we go?

Like more than 75% of the baby boomers surveyed by AARP who said they took their last flight to a domestic destination, we planned to stay in the US. My husband’s top pick was Chicago. I had never been and wasn’t sure what there was to do in the Windy City, but agreed to check it out.

Am I glad I did! If you go, what should you do? Where should you stay? Where should you eat? Here is my itinerary along with some tips:

Day One: The Whitehall Hotel and John Hancock Center

The View from the John Hancock Center

The stunning view from the John Hancock Center.

We landed in O’Hare at about 3:00 p.m. and took the “L” train – or Chicago’s version of the subway – into the city. Here’s my personal opinion and first piece of advice. Whether you’re in New York, London, or Chicago, if you want to get a true feeling for the city and its residents, forget the tour buses for seniors and taxis. Ride the subway as much as possible.

Second piece of advice: use Hotwire. Maybe you’ve had a different experience, but they haven’t steered me wrong yet. The disadvantage is you don’t know exactly where you’ll be staying until you book it, but that’s part of the adventure and you usually pay about half price. I typed in a four star hotel and ended up at Whitehall Hotel. An older, remodeled hotel in Magnificent Mile (the swanky area of Chicago with expensive shops and trendy restaurants) with a super friendly doorman. Great stay.

chicago the tilt

The Tilt – and yes, it tilts down to give you that extra sense of vertigo.

We only had a few hours, and the John Hancock Center was a block away, so that’s where we headed. The observatory is now called 360 degree Chicago with spectacular views of the waterfront and Chicago’s famous skyline.

Although there is much debate whether the John Hancock Center or Willis Tower (formerly Sears Tower) is the better option, we decided to do both. So which one did I think was better? Hard to say. John Hancock had a better view of the waterfront, a bar where we sat and had a drink (there’s no such place at Willis), and The Tilt.

Now, another thing we baby boomers are looking for in a vacation is some adventure. If you go, live a little! For an extra $7 you can lean against a glass wall that actually tilts down so you can have an extra dose of vertigo from 1,000 feet up. Fortunately, it wasn’t crowded the day we went and I didn’t get a chance to see how this worked before I jumped on – and was shocked the wall actually moved. I know, I know, it’s called The Tilt. What did I think was going to happen! At any rate, I’m afraid of heights and am darn proud I did this!

Willis Tower (which I write about below) has the famous Skydeck and a better view of the river. It is a bit expensive, but since we didn’t know when we would return to Chicago, we splurged and did both. No regrets.

Since we baby boomers also like a bit of luxury when we travel, we had dinner at Fornett Mei. This charming Italian restaurant, conveniently tucked next to Whitehall, has plenty of ambiance, phenomenal service, and great food. We had a specialty thin crust grape and sausage pizza. Sounds like an odd combination, but it was delicious.

Day Two: Willis Tower, Cloud Gate, River Walk, and Sunset Cruise

chicago skydeck

I’m afraid of heights but got up the nerve to sit on the famous Skydeck – over a thousand feet in the air with a glass bottom.

We jumped the subway and started day two at Willis Tower. I figured we’d get my fear of the heights completely out of the way so I could enjoy the town with my feet firmly planted on the ground the rest of the time. The elevator ride itself was exhilarating. Up 103 floors in 90 seconds with a video that lets you know when you are as high as the Statue of Liberty and the Eiffel Tower. Freaked me out a bit, but interesting. When you get off the elevator you’re a whopping 1,353 feet in the air with great views 50 miles out and you can actually see four states on a clear day.

Okay, let’s talk the Skydeck. These famous scary glass boxes extend out four feet with views all the way down. As I mentioned before, even though I’m afraid of heights, I was determined to do this. I’ve had a rough few years and I just wanted to start living again. The secret? Don’t look down. Step out, refuse to think of how high up you are, and look straight at the camera thinking of the awesome photo you’ll have to share with family and friends. I only looked down as I was ready to safely step off. The view was terrifying, but I’m still happy I did it.

chicago cloud gate

The view from underneath Chicago’s famous landmark, Cloud Gate, nicknamed The Bean because of its shape.

Next stop. We walked to Cloud Gate in Millennium Park for some cool pictures. Be sure and walk around this beautiful park in the middle of the city.

One interesting sight is the Crown Fountain with two glass block towers at each end of a shallow reflecting pool. The towers project faces of Chicago residents with water flowing through an outlet that makes it look like water is spouting from their mouths.

Then off to the River Walk with spectacular views. We ate at O’Brien’s – great hamburgers, good service, and the perfect spot to relax on the river.

chicago river walk

The gorgeous River Walk where you can catch a boat tour, walk, or rent a kayak.

 

My sister, Joanie, booked us a sunset cruise for an anniversary present which included an architectural tour of the city’s famous buildings at dusk, then a cruise ride on Lake Michigan for views of Chicago’s magnificent skyline after dark. Very romantic!

If you take one of the sunset cruises you can see Chicago's skyline during daylight, sunset, and at night.

If you take one of the sunset cruises you can see Chicago’s skyline during daylight, sunset, and at night.

Day Three: Sailing Lake Michigan

Me and hubby own a sailboat and have been sailing for 30 years. We rented a boat and took a relaxing sail on Lake Michigan, the second largest Great Lake, with Chicago’s skyline in the background. The wind was great! You can rent a captained boat if you don’t know how to sail.

Sailing from Belmont Harbor.

Sailing from Belmont Harbor.

Another transportation hint: Taking the subway to Belmont Harbor, located in Lincoln Park, seemed a bit complicated, so we called Uber. I personally prefer Uber over taxis. The drivers seemed more relaxed and friendly. In fact, as a writer, I enjoyed getting their life stories.

As a bonus, most, but not all, had lived in Chicago their entire lives and were happy to make recommendations.

We just happened to be there when the Louis Vuitton America’s Cup World Series Chicago at Navy Pier was taking place which put my husband in seventh heaven. After watching the trials, our Uber driver and other locals recommended the very casual Al’s Italian Beef for a typical Chicago meal. We ate their award-winning steak sandwich with sweet peppers. Yum. If you visit Chicago, also try their specialty popcorn – a delectable combination of sweet caramel and savory cheese.

Of course, you can’t visit Chicago without trying their signature deep dish pizza. Lou Mainati’s Pizzeria on Rush Street was recommended by a local and within walking distance of our hotel. Tried their famous recipe that has been handed down through generations and considered one of the oldest family names in Chicago and fell in love!

Day Four: The Art Institute of Chicago

chicago art museum

The famous American Gothic at the Art Institute of Chicago.

Okay, this is going to make me sound terrible and uncultured, but museums are not normally at the top of my list of things to do when visiting a new place. I’d rather be outside having new experiences.

Except in big cities with museums brimming with impressive and stunning collections. In New York, you must see the Met and when you visit Paris you’d be remiss not to see the Louvre. Chicago has many world-acclaimed museum, but perhaps most famous is it’s Art Institute. With more than 300,000 artworks and artifacts from all over the world and every era, famous modern and contemporary art, and fabulous views of Millennium Park, it’s a must-see. Bonus for me – the miniature rooms – which I’ve been fascinated with since I was a kid. Even Ferris Bueller visited the museum. He had the right idea.

One of my sister’s friends, a former Chicago resident, recommended Carmine’s on Rush Street for dinner. On Magnificent Mile, it was fun watching the Lamborghini’s pull up with the happening crowds dressed to the nines. Affordable for downtown Chicago, the food was fabulous. We had baked clams as an appetizer – to die for!

Ah, alas, time to go home. After watching the news recently about three hour waits at O’Hare, we got there nice and early. We got through security in about 10 minutes and then had a lot of time to kill. We were the first ones at our gate. Guess everyone else knew better and somehow I didn’t get the memo!

As you can tell, I fell in love with Chicago. It ranks right up there with my other favorite cities: Sydney, Seattle, London, and Paris. If you ever get the chance, don’t miss visiting this welcoming, clean, exciting, and fun city!

3 thoughts on “Chicago Great Vacation Trip for Baby Boomers

  1. Cat Michaels

    Wow, Julie! You’re way braver than me to sit on that ledge and tilt it! I went to the windy city once on business long ago and would love to return to see the sights for leisure. Thanks for sharing!

    Reply
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