Perfect Chicago Weekend Itinerary

My recent trip to Chicago was such a great experience. It was made absolutely perfect with the amazing group of friends we traveled with and a well planned itinerary. We were celebrating two friends’ 30th birthdays, and had a jam packed agenda. We did pretty much everything on our must see list for our first time in the Windy City. We were there for a long weekend and it was definitely the perfect amount of time to explore this amazing city.


We arrived early on Friday morning and took the Blue Line into the city. It was about an hour ride from the airport and only $5 a ticket, which definitely beat getting an Uber and sitting in traffic. We walked to our hotel from the train stop, which was only about 15 minutes and a few blocks away.

Crossing the Chicago River

We were staying at the Best Western and the location was great! Walking distance to pretty much everything.

Once we checked in and freshened up at the hotel, we ventured out to find a great place for lunch before heading to Navy Pier for an Architecture River Cruise.

The Purple Pig was one of my favorite places from the trip. The food was so delicious, the sangria was absolutely divine and the swine was especially fine. (I think that is a line from one of my daughter’s storybooks.)

The Purple Pig - Chicago We scheduled an architecture river cruise by Shoreline Sightseeing for 3:30pm and headed to the Navy Pier to board the boat (with bar!) for a tour of the city on the Chicago River. The cruise cost $32 if booked online.

River Cruise - Chicago

River Cruise - Chicago

River Cruise - Chicago

On our walk back to the hotel we stopped off at a few places for some photo ops, drinks and apps at City Winery on the river and theWit rooftop bar, where we met up with my good friend Courtney who lives in Chicago.


River Backdrop Photo Op

The Witt - Chicago

theWit rooftop


Night Time City River Photo Op

That night we hit the town at some neat spots like the Joy District rooftop bar and Social Twenty Five that had a great live band playing popular music.

Joy District - Chicago


Saturday was game day. First, we hit up Beatrix for a delicious breakfast.

Beatrix - Chicago Beatrix - Chicago

Then headed for the train to Wrigleyville for the Cubs game.


We met up with some more friends at the bars in Wrigleyville right outside the stadium and watched some college football before we headed into the stadium for the game. 

Old Crow - Chicago Murphy's - Chicago

Group Selfie at Murphy's

Group Selfie at Murphy’s

Wrigley Field - ChicagoWrigley Field

After the game we got some dinner at Old Crow, a country themed bar with a rooftop area and some delicious BBQ pork tacos.

Old Crow - Chicago


Sunday was the ultimate Birthday Bash, celebrating the lovely Stephanie’s big 3-0 with a delicious brunch at Fremont.

Freemont - Chicago Freemont - Chicago

The place gets packed and you need reservations. The brunch buffet was great and there’s unlimited mimosas with multiple flavored mixers. Our seat was right near the DJ and we jammed there until about 2:00pm! Until we got kicked out. Which was probably good, ’cause we had a lot to see!

Freemont - Chicago

Freemont - Chicago We headed in an extra large Uber and headed to Millennium park to see the iconic Bean.

Millennium Park - Chicago

Millenium Park - Chicago

The Bean - Chicago

Then we had to see the sunset atop of the John Hancock Building. We Ubered there to make it to the top in time to order some champagne and admire the city from above.

John Hancock Center - Chicago

What’s great about seeing the view from the John Hancock Building is that it’s free to get in, unlike the Willis Tower. We got to sip delicious champagne at our own table in the bar at the very top and didn’t have to wait in any line full of tourists. John Hancock Center - Chicago

For dinner that night, we had to try some deep dish Chicago style pizza. We originally had reservations at Giordano’s but apparently there are several of them in the city and when we arrived at the wrong one, twice, we decided to go to Lou Malnati’s, which was a 5 minute walk from our hotel. It was way more rich than we thought it would be and one piece was definitely enough. We had lots of leftovers.


Monday was our last day in the city and we had a plane to catch in the afternoon around 5pm. We started the day with a walk down the street to Yolk for breakfast.

Yolk - ChicagoYolk - Chicago

It was so yummy and lots of food!

Yolk - Chicago

Then we headed to the Navy pier to take some photos and try the famous Garrett’s popcorn.

Navy Pier - Chicago

Navy Pier - Chicago Navy Pier - ChicagoNavy Pier - Chicago We walked the beautiful Michigan Mile for the remainder of the day and ended our exploration at the famous Portillo’s for one last Chicago Dog before heading to the train station for our ride back to the airport.

Portillo's Chicago Portillo's Chicago Dog

We were totally exhausted by then, and extremely satisfied with our amazing trip. It was time to head home, but we are already planning our next trip back.

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