Chicago in Three Days – Go Cubs Go

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Day One:

Mike was in Chicago for business over my 50th birthday and I joined him as part of the celebration. We stayed at the Four Seasons in downtown Chicago, just steps from the Magnificent Mile, Chicago’s upscale section of Michigan Avenue. (The John Hancock building was across the street from our hotel and we could see it from our window.) The Four Seasons is a spectacular hotel and their service was top notch. Here are a few pictures of the room we stayed in.

Four Seasons
Four Seasons
Four Seasons

On the day I arrived in Chicago, Mike was still working, so I did some window shopping at Water Tower Place and in the Bloomingdales Mall, connected to our hotel. Later on, I headed to Ditka’s for a beer and a light dinner. I sat at the bar and watched the Cubs beat the Dodgers. Go Cubs Go!!

Day Two:

On Day Two, Mike and I headed out for breakfast at Sunny Side Up. They have an excellent rating on Trip Advisor (our go-to app for traveling) and they didn’t disappoint.

Sunny Side Up

We ordered Pumpkin pancakes and Eggs Florentine – both were delicious. Mike and I almost always order several things to share, so we can taste as much as possible. I think that means either we’re getting old or that we really like food.

Ok, both.

Pumpkin Pancakes
Eggs Florentine

And yes, we’re the geeky tourists who snapchat/take pictures of our food. All the time.

#ourboysthinkwearecool – haha!

After breakfast, we ventured down Michigan Avenue to window shop. Mike is lucky because  I’m a cheap travel date and not all that interested in the shopping part. I’d rather see the sights, eat good food, and take pictures! I can shop in Dallas anytime and one only needs so many pairs of jeans and t-shirts.

Mike definitely wanted to check out Millennium Park, so we headed south and crossed the Chicago River. It was a chilly, windy day – typical for Chicago.

With 25 acres of awe-inspiring landscape, amazing architecture and an iconic collection of public art, Millennium Park is Chicago’s premier green space. Once in the park, we bee-lined for Cloud Gate, the official name for the massive, stainless steel structure that’s become Chicago’s signature landmark. In its mirror-like surface, you can see the downtown skyline as well as your own reflection. We took a bunch of pictures – along with hundreds of other picture-taking locals and tourists.

Millemmium Park

We walked past the Art Institute of Chicago (we are NOT museum buffs and prefer the outsides of museums better than the insides…) and on toward Lake Michigan.

Renting bikes has become an absolute when Mike and I vacation together. So we rented two Divvy Bikes and were on our way up Lakefront Drive, (which runs parallel to Lake Shore Drive) along Lake Michigan.

Divvy is Chicago’s bike share system with 580 stations and close to 6,000 bikes around the city. We purchased a 24 hour pass and were able to park the bikes in different locations, as we hopped on and off (in 30 minute increments) throughout the afternoon. I highly recommend this way of sight-seeing around Chicago. Just make sure you return your bike before 30 minutes are up. We didn’t realize we would get charged late fees for having the bikes out for longer than 30 minutes at a time. But regardless, we had SO much fun.

We dressed in layers for our biking adventure as the day started out pretty chilly. Navy Pier was one of our first picture-worthy stops.

Navy Pier

The views along Lake Shore Drive were pretty awesome. We were biking AGAINST the wind on our first leg going north, and the waves were crashing up onto the boardwalk at times.

Divvy Bikes

We pedaled up to Lincoln Park, which is a North Side neighborhood. It’s namesake park is a sprawling 1,208 acres of green space with a free zoo open year-round, a nature museum, and conservatory. We got off the trail at Lincoln Park and headed west to check out the brownstones, the three and four story historic homes in this part of the city. These homes sell for several million dollars and are the crown jewel of Chicago’s lakefront neighborhoods.

Lincoln Park, Chicago

Since we were in the area of Wrigleyville, the home of the Chicago Cubs, we knew we had to continue north. So we hopped on Sheffield Avenue and kept on pedaling. It was the day before game 6 of the playoff series against the Dodgers and the area was humming. My fingers were numb, so we got a quick pic in front of the stadium and headed to the nearest Starbucks to warm up.

Wrigley Field

From there we pedaled back toward our hotel, along Lake Shore Drive. The city views were SO amazing.

Lake Shore Drive

Dinner that night was at Lou Malnati’s Pizzeria, home of the best pizza in Chicago – in our opinion. Ask Mike – he ate there THREE times in ONE week! Their Chicago-style deep dish pizza is made using a recipe that has been handed down through the generations. It’s so filling that two pieces usually feeds one person. Yum.

Lou Malnati's

After dinner, we went to see the musical, Wonderful Town, at Goodman Theatre. Mike knows how much I love musicals and surprised me for my birthday. It was spectacular!

Day Three.

We started Day Three with another hearty breakfast at West Egg Cafe, an American Diner that was within walking distance from our hotel.

West Egg Cafe

The diner was bubbling with customers and the line for a table was literally non-stop. Our food was once again, delicious. We shared the Bacado Omelette and the Blueberry Crunch Pancakes.

West Egg Cafe

With plenty of fuel in our bellies, we rented two Divvy Bikes again. Biking Chicago was our favorite part of the trip. I highly recommend you try it, especially when the weather is right.

Divvy Bikes

We knew the trail went north past Lincoln Park and decided to just keep pedaling until we couldn’t pedal anymore. 🙂 We made it all the way up to the end of the lakeside trail in the Loyola Park area and took a detour through Loyola University. The campus is located directly on the shores of Lake Michigan and unbelievable beautiful. Oh to be a student again!!

Loyola University
Loyola University

After our college visit (haha!), we hopped on our bikes and headed south, back along Lakeshore Drive, toward the Four Seasons. Our breakfast fuel had long worn off, so we treated ourselves to the biggest sundae on the Ghirardelli’s menu – a Salted Caramel Brownie Sundae (for two).


The final event of our trip involved the Chicago Cubs, a group of college friends, and a bar (FULL of Cubs fans).

Mo's Cantina

We met at Mo’s Cantina, about a mile from our hotel. We hadn’t seen this group of friends in close to two decades (crazy!) so it was long past due. And we brought the Cubs some luck because we watched them clinch the National League Penant in a 5-0 win against the LA Dodgers.

Go Cubs Go!! (And yes, we’re still #1 Ranger fans..)


Check out a little video Mike did while biking in Chicago…or click on the video link in the sidebar above.


  1. My brother lives in Chicago and Sunny Side up is SO GOOD!!! Glad you are having a great time!

    1. Suebee Homemaker says:

      Yes, we had a great weekend there. We actually used to live in Chicago. I should have included that in the blog post!

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