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 Chicago weekend itinerary. We were celebrating two friends’ 30th birthdays, and had a jam packed agenda. It was a long weekend and it was the perfect amount of time to explore this amazing city.
Friday
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. The walk to our hotel from the train stop was only about 15 minutes and a few blocks away at the Best Western. It was the perfect location and 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.)
We scheduled an architecture river cruise with Shoreline Sightseeing for 3:30pm and headed to the Navy Pier to board the boat (with a bar!) for a tour of the city on the Chicago River, where else!
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.
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.
Saturday
Saturday was game day. First, we hit up Beatrix for a delicious coffee and breakfast.
Then we head for the train to Wrigleyville for the Cubs game. Being able to go to a Cubs game while in Chicago was such an amazing experience. The vibe all around the stadium was so much fun, and the Chicago Dogs were the best I’ve ever had.
We met up with some more friends at the bars in Wrigleyville right outside the stadium and watched college football before we headed into the stadium for the game.
Afterwards, we got some dinner at Old Crow, a country themed bar with a rooftop area and some delicious BBQ pork tacos.
Sunday
Sunday was the ultimate Birthday Bash, celebrating the lovely Stephanie’s big 3-0 with a delicious brunch at Fremont.
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!
Our next stop was Millennium park to see the iconic Bean.
It was almost sunset, so we head straight to the top of the John Hancock Building for champagne and an amazing view of the city.
What’s great about seeing the view from the John Hancock Building is it’s free to get in, unlike the Willis Tower. We got to sip delicious champagne at our own table in the bar and didn’t have to wait in a line full of tourists. (And ladies, check out the view from the bathroom, because it is amazing.)
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
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.
It was so yummy and lots of food!
Of course we had to make a stop at this amazing painted wall for a photo op, right down the street from our hotel.
Then we headed back to Navy Pier to explore and try the famous Garrett’s popcorn.
For the remainder of the day we walked the beautiful Michigan Mile filled with amazing shopping 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.
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.
This Chicago weekend itinerary is a great starting point for an amazing trip. If your looking for another amazing itinerary, check out our girls weekend in weekend in New Orleans.
