A weekend in ‘The Windy City’ Chicago (Guest Post)

One of the destinations on my bucket list is definitely ‘The Windy City’ Chicago! Unfortunately, it seems that travelling has to wait for some time so instead I wanted to give you some inspiration through a guest post by Traveling Tanya!

Guest post by Traveling Tanya

Hi, I’m Traveling Tanya! I have lived in Indiana most of my life, but I love traveling all around the world. As a busy mother, wife, employee, and volunteer, it’s not always easy to find the time or the money to travel. But as they say…where there’s a will, there’s a way!

I love sharing my travel adventures and tips at travelingtanya.com with the goal of inspiring busy people to make travel a priority. I like to remind my followers that some of the best destinations may not be all that far away. For me, I’m fortunate to live just a hop, skip and a jump away from Chicago!

Traveling Tanya in the Windy City Chicago

Chicago is a bustling city full of amazing art, impressive architecture, oodles of stores, fine dining, and much more. Whether you are looking for a family-friendly vacation, a romantic getaway, or even a solo adventure, Chicago has plenty to offer.

Chicago is located in the heart of the Midwest, making it accessible to so many.

For our 7th anniversary, my husband and I decided to skip the typical flowers, jewelry, and traditional gifts used to show undying affection. Instead, we agreed to spend our money on travel, rather than “things” as a way to commemorate our love.

Chicago was the perfect spot for our weekend anniversary celebration!


Since we both had to work on Friday, we couldn’t leave Indianapolis until after 5pm. We wanted to get our anniversary weekend started but didn’t like the idea of getting stuck in Chicago’s Friday night traffic. Plus, we hated to pay the high city hotel rate when we wouldn’t have much time to enjoy it.

The perfect solution was to head to Merrillville, Indiana! Just 1 hour outside of Chicago, we knew spending the night in Merrillville would position us to hit Chicago early on Saturday and save a little money in the process.

Where We Stayed

The Clarion Hotel in Merrillville provided everything we needed. It was close to the highway.  Free parking was included.  Our room was comfortable, clean, and spacious. There were several restaurants close by, and the hotel provided a free hot breakfast.

And by booking through Expedia, it cost just under $100.  There was also a nice indoor pool, but we didn’t take time to enjoy that feature on this trip.

Where We Ate

In the busy commercial area around our hotel, there were plenty of chain restaurants to choose from. We debated about grabbing dinner at a few of our tried and true favorites, but I was hoping for something a bit more fun and different to kick off our anniversary weekend.

We ended up choosing Old Chicago Pizza and Taproom, which was actually the closest restaurant to our hotel and seemed fitting for our Chicago themed weekend. While Old Chicago is a chain restaurant, we don’t have any near home, so it felt like we were venturing out of our dining rut. And it turned out to be a fabulous experience!

old Chicago the windy city chicago

We bellied up to the expansive bar, taking in the lively atmosphere. With over 100 craft beers on tap, that is the drink of choice for many diners. Since I’m not a big beer drinker I was excited to learn that Long Island Ice Tea was the Friday drink special.

Even though pizza is in the name, Old Chicago offers a huge selection of tasty options. It was the BBQ bacon burger with sweet potato fries for me and fried pickles to share. Brent ordered the chicken fried chicken, but there was a snafu with the chicken in the kitchen. The wait staff really stepped up to the plate to make things right, and Brent decided to join me in devouring a tasty burger, on the house. Once the chicken was ready they gave us that too in a to-go box!

Great service, delicious food, strong cocktails, and a handsome date. It was the perfect start to our anniversary weekend.


After enjoying the free breakfast in the hotel lobby and a quick caffeine run to Starbucks, it was time to head for the Windy City!

the windy city chicago

Traffic was light (for Chicago) and the sun was shining. Thanks to Spot Hero we already had a parking spot reserved in a garage less than a block away from our hotel. This handy app helped us save $18 on parking!

Where We Stayed

Earlier in the week we searched numerous hotels on Expedia and selected the Doubletree By Hilton Chicago Magnificent Mile. (I had recently added the Wikibuy extension to my web browser and it popped up with an even better rate through HotelStorm, so I snagged an extra $13 savings!)

hotel Chicago

The Doubletree provides some amazing amenities, although we spent most of our time exploring the city and didn’t get to take full advantage of them. Just a short walk to Navy Pier, the hotel’s location couldn’t be beat. With a Starbucks in the lobby, a full array of grab and go sandwiches and salads for sale, and free fresh baked cookies at check-in, we were not going to go hungry.

We will definitely stay at this hotel again on future trips to Chicago, and next time we will factor in time to enjoy the 5th-floor outdoor pool and bar!

pool hotel chicago

What We Did

We made a beeline for Navy Pier. The flowers were in full bloom, and people were enjoying the beautiful day along Lake Michigan. We strolled through the shops, numerous food vendors, and the botanical gardens with dancing fountains.

Navy Pier the windy city Chicago

While we weren’t quite ready for a cocktail, we did sneak a peek at the rooftop restaurant and bar, Offshore. This is the largest rooftop venue in the U.S., and it’s quite impressive!

offshore Chicago

We also ended our day at Navy Pier as we took in the delightful display of fireworks over the water. Held every Wednesday and Saturday evening from Memorial Day to Labor Day, this is the ideal way to cap off a romantic evening in Chicago.

fireworks Chicago

In between our trips to Navy Pier, we decided a great way to explore the city would be from the top of the Hop-on-Hop-off bus.

hop-on-hop-off bus the windy city Chicago

Insider’s Tip: When purchasing tickets, if you show a screenshot of the discounted rate on Groupon at the ticket kiosk. they will honor the lower rate!

With clear skies and a big city to see, we took our seats on the top of the open-air bus and enjoyed the ride. Our tour guide gave plenty of insightful and witty commentary and even provided sunscreen to passengers, like me, who forgot this important travel accessory.

It was here that I learned the real reason Chicago is referred to as the Windy City. It is much more about the hot air coming from local politicians than it is a reference to the weather conditions along Lake Michigan!

We also took advantage of the coupon for a free bag of popcorn from Garrett’s that comes with every Hop-on-Hop-off bus ticket. It’s a Chicago tradition!

Where We Ate

Our tummies were rumbling, so we hopped off the bus at Millenial Park for a late lunch. The timing ended up being perfect. As we sat under an umbrella at The Plaza at Park Grill with cocktails in hand, a 15-minute rain shower took everyone by surprise!

Park Grill food

The city cooled off a bit, but we stayed dry while my husband enjoyed a tasty burger and craft beer, and I indulged in a frozen margarita and a loaded salad.

Nothing goes better with day drinking next to the one you love than good live music! When familiar tunes started up on the nearby stage it made for the perfect lunch outing.

the Windy City Chicago

Much later in the evening and after a brief rest at the hotel, we got spiffed up for our anniversary dinner. My husband had made reservations through earlier in the week at The Dearborn. He indicated in our reservation that we were celebrating our anniversary, and The Dearborn really pulled out all the stops and made it special!

cheers card the Dearborn Chicago

We were promptly seated at the best table in the house, an intimate round booth by the window. Glasses of champagne and a card were quickly presented to us.

food the Dearborn Chicago

The sweet lady at a nearby table overheard the celebratory nature of our dinner and sent the daily fish taco special to our table. Mind you, this was no Taco Bell taco…it was absolutely delicious and high class. Chicagoans are so sweet!!

For something a bit different, we selected the Shrimp and Octopus Ceviche for a starter. It was bursting with flavor…so good!!

food the Dearborn the windy city Chicago

Already starting to feel full and keeping with the seafood theme, we decided to split the fish and chips. The portion size was just right to share, and my husband moved on to a martini while I ordered more champagne.

The waiter offered us a free dessert to continue our celebration, but I was too full to partake. That may be the only time I’ve turned down free food! I was perfectly satisfied and happy to enjoy this special night with my husband without being uncomfortably stuffed.

If you are looking for a romantic dinner venue in Chicago, you can’t go wrong with The Dearborn!

Traveling Tanya and husband


Feeling well-rested and excited to see even more of the city, we got out early on Sunday morning. We knew it would be a different vibe than the hustle and bustle of the city crowd the night before, and we were anxious to walk and beat the heat of the day.

What We Did

We strolled south from Navy Pier on the walk and bike paths along Lake Michigan. Locals whizzed by us on foot, bikes, and rollerblades as we took our time enjoying the city skyline.

the windy city Chicago

After cutting across Millennium Park, we continued to wind our way through the still sleepy city streets taking in the architecture and charm of Chicago.


We logged quite a few steps that morning! While this might not sound romantic to some, I love spending time just walking with my husband and seeing new sights together. And Chicago provides a beautiful backdrop for a stroll with the one you love.

the windy city Chicago

Where We Ate

As late morning approached, our quest for the perfect breakfast cafe came to an end at Troquet River North.

Sitting at a lovely outdoor table, my husband fueled up on coffee, eggs, and bacon. I indulged in the buttermilk pancakes with blueberry custard.  They were as tasty as they were beautiful!

food Troquet River North Chicago

Sadly, our weekend in Chicago was coming to an end.

As we left town, we took the scenic route north along the river. Envious of all the beachgoers enjoying this perfect summer day, we vowed to return soon. And of course, we had to make a quick drive past the famous Wrigley Field! No time for a Cubs game today…but someday soon!

Next Time

With so much to see and do in the Windy City, you can bet we will be returning! Next time I’d love to add a river cruise to our itinerary and check out one of the many rooftop bars. I’d totally be up for seeing a live theatre performance, and I know my husband would love to take in a Cubs game.

husband Traveling Tanya

With teenage girls who love to shop, a family trip to Chicago with a stroll down the Magnificant Mile is also on my radar. A visit to the Ghiradelli ice cream shop will be on the must-do list.

My youngest daughter gets to take a day trip to Chicago with her school choir next year, and they will hit the Shedd Aquarium and some of the other world-class museums.

That’s one school trip I may want to chaperone!

Chicago goody bag

Have you visited the Windy City lately? For even more ideas on things to explore, check out Choose Chicago. And be sure to visit travelingtanya.com to learn about many more fabulous destinations and useful travel tips.

Did you like Traveling Tanya’s guest post about the Windy City Chicago? Let me know in the comments!

For more inspiration about city trips read my blog posts about Canada or check out my post about Boston!

A weekend in the windy city Chicago

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