Romantic Weekend in Chicago

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

Being located in the heart of the Midwest, Chicago is accessible to so many. Yet somehow my husband Brent and I had never taken a trip to Chicago together. And we only live 3 hours away in Indianapolis!

When our 7th anniversary rolled around we decided to skip the typical flowers, jewelry, and other gifts often used to show undying affection. Instead, we agreed to spend our money on travel, rather than “things”, to commemorate our love.

We decided it was high time we explored Chicago together!

Friday

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 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!

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. But 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.

Saturday

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

Traffic was light (for Chicago) and the sun was shining. And 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!)

The Doubletree provided 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!

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.

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!

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.

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

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 because 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!

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

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

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

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.

A lady at a nearby table overheard the celebratory nature of our dinner and sent us the daily fish taco special. 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!!

Already starting to feel full and keeping with the seafood theme, Brent and I split the fish and chips. The portion size was just right to share, and Brent 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!

Sunday

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 the lake. Locals whizzed by us on foot, bikes, and rollerblades as we took our time enjoying the city skyline.

After cutting across Millenial 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.

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, Brent fueled up on coffee, eggs, and bacon. I indulged in the buttermilk pancakes with blueberry custard.  They were as tasty as they were beautiful!

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 famous Wrigley Field! No time for a Cubs game today…but someday soon!

For a quick recap of our fun in Chicago, watch this photo montage:

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 know Brent would love to take in a Cubs game, and I’d totally be up for seeing a live theater performance.

With teenage girls who love to shop, a family trip to Chicago with a stroll down the Magnificant Mile is also on my radar. And 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!

But this trip was all about me and my love. Happy Anniversary, Brent!

There is no one else I’d rather be navigating this world with…I love you!

Have you visited the Windy City lately? I’d love to hear about your favorite things to do in Chicago! Please share in the comments below. And for even more ideas on things to explore, check out Choose Chicago.

Wherever the road takes you, make it a joyous journey,
Traveling Tanya

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