Monday, September 11, 2023

Chicago, IL & Milwaukee, WI | September 1 - 5

Chicago, Illinois 

Where we stayed:

The Congress Plaza Hotel & Convention Center

This hotel is said to be haunted. One room so much so that it can only be booked by specific request. Thankfully, any ghosts in our room weren't active the night we slept there.

Day 1

Willis Tower / Skydeck & The Ledge

The Willis Tower (formerly Sears Tower) was the tallest building in the world from 1974 until 1998. It has 108 floors, and floor 103 is home to the Skydeck. The Skydeck is a museum that shows Chicago highlights and the process of building the Willis Tower. There is also a feature called "The Ledge," which are clear observation boxes that protrude from the building. I'm not going to lie: the first step onto The Ledge is a little bit daunting, but standing over the city (and snapping some selfies) is a really cool experience.

Gin Alley

This one we could have skipped. I saw it on TikTok and thought it was going to be bigger than it was. It's basically an outdoor shopping area in the city. We got there too early for any of the bars to be open, but my sister did make a purchase at Uncommon James. If you're staying close to Gin Alley, give it a whirl, but don't walk an extra mile like we did to essentially turn right around.

Chicago Riverwalk

Now, this is where you're going to want to walk. The Riverwalk in Chicago is gorgeous. There are places to stop to sit or drink (we stopped at more than one) and look out onto the river, which always has something happening between all of the tour boats, personal boats, kayaks, etc.

O'Brien's Riverwalk Cafe

After the Riverwalk, we went back to the hotel to rest for about an hour (my sister and I had started our days early to make our 6 a.m. flight, so it was a necessary refresh). Then we went back to the Riverwalk for dinner at O'Brien's. Some of the fastest service I've ever had. We thought we'd be there until the start of our tour, but the food came out so quickly that we had time to visit one more bar beforehand.

London House Rooftop

I love a rooftop, and anything with London in the name is going to catch my eye. Getting a dinner reservation at London House is a multi-year wait, but we could head straight up the elevator and walk right into the rooftop bar. Excellent views and pretty good drinks. We also went one floor down to LH on 21 and got one final drink inside before getting to our tour meeting spot.

Gangsters and Ghosts Tour in Chicago

This was the tour my sister found, and was very excited to walk around Chicago with a tour guide. She thought it would be more spooky ghost story-esque than it was, but it was still great. I had no idea there were so many mass deaths in Chicago (boats sinking in the river, more than one fire taking out hundreds of people at a time). And then, on top of that, the gangsters fought over territory throughout the late 1920s. Al Capone (I kept saying Pacino, but that's the actor who played Al Capone in the movie Scarface. There are too many Al's) was building a name for himself and taking out quite a few people along the way. 

Day 2

Eleven City Diner

This was recommended by a friend, and it did not disappoint. More food than we knew what to do with, but it was delicious. And diners always tend to have a fun atmosphere.

The Bean

You can't go to Chicago and not see the Bean (aka Cloud Gate). Unfortunately, a fence was around it, so we couldn't get up close and personal, but we did see it!

Shoreline Sightseeing: Architecture River Tour

In the late 1800s, most of Chicago burned to the ground. But a cool consequence of that was when they rebuilt the city, they could do so with a little bit more of a plan than they had before, which led to some really innovative architecture. Today, the Chicago skyline still embraces architecture of all kinds. Going down the river and learning about the different styles and what people did to make their buildings stand out was really interesting.  

Wrigley Field Tour

The Cubs were out of town while we were in Chicago, so we decided to tour the stadium instead, which is arguably more fun. Wrigley Field was built in 1914, making it the second oldest Major League Baseball stadium in the world (Fenway was built in 1912, and Dodger's Stadium is the third oldest and was built in 1962). And with old ballparks come some amazing stories. Wrigley Field didn't have lights for years; it was forced to adapt to the changing city around it, and its fans (especially the Bleacher Bums) are the reason behind not only Wrigley Field safety features but also played a role in the MLB "batter's eye" rule.  

Smoke Daddy BBQ

Across the street from Wrigley Field is a BBQ restaurant (discounted with our Wrigley Tour ticket!) that we stopped at before driving to Milwaukee.

Milwaukee, Wisconsin 

Milwaukee is a huge brewery city. Each one is unique in its own way, and I enjoyed all of the ones we went into, but writing about each one was getting repetitive, so I decided not to.  

Where we stayed:

My brother's apartment

Free accommodation is always a perk.

Day 1

Cafe Hollander Tosa Village

This was in Wauwatosa, which is closer to my brother's apartment. It was in the cutest downtown area. We didn't explore because we had to get to the game, but spending an extra 15/20 minutes walking around would have been nice.

American Family Field / Brewers Game

Another city, another ballpark. However, it was for a game this time because the Brewers were playing the Phillies. They unfortunately lost, but it was a fun game to watch.
FUNNY STORY: At one point, a woman came walking down the stairs holding a hot dog and asking if anyone lost it. Turns out it had slipped out of the tin foil a little boy was holding. He took it back and ate it (5-second rule; it was fine lol), but all I could imagine was having to turn to my own dad and somehow explain that the overpriced hot dog he bought me three minutes ago vanished from my hands.

The Copper Turtle Brewery & Taverne

The Explorium Brewpub Third Ward

Cafe Benelux

Blue Bat Kitchen and Tequilaria

Day 2

MOTOR Bar and Restaurant

Harley-Davidson Museum

I've never been on a motorcycle, but I know a handful of people who own them and since we were in Milwaukee, we had to stop and check out the museum. It was cool to see how motorcycles have changed over time.

National Bobblehead Hall of Fame & Museum

It's a unique museum, for sure. Lots of athletes and presidents/famous figures. So many Grittys. We didn't do it because it was more for kids and not offered to us, but there was also a scavenger hunt element.

Broken Bat Brewing Co

Great Lakes Distillery & Tasting Room

MobCraft Beer Brewery Taproom and Pizza

Shakers Cigar Bar

Day 3


This was a good breakfast place. Located in Elm Grove, not Milwaukee. You could tell it was the first day of school because a group of moms (possibly some nannies) were all at a table together, toasting to drop-off.

Pabst Mansion

The Pabst Mansion, built in 1892, is a grand Flemish Renaissance Revival-styled house and was the home of Captain Frederick Pabst, founder of the Pabst Brewing Company. Each room has a slightly different style based on who used it and for what purpose. The street it's on used to be all mansions, but now Pabst is the only one. 

War Memorial Beer Garden

Lakefront Brewery

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