People often ask us how we can travel so much. “Do you have unlimited PTO?” they ask. Well, no. But by planning short weekend trips, we get the most bang for our buck while still exploring new cities..
Here is how you can maximize your adventure with the best weekend itinerary for Chicago!
Where to Stay
We stayed at the Aloft Chicago Mag Mile. This hotel is reasonable priced, has modern decor and a busy lobby bar. It’s the right place to get your weekend going. There is even live music on Friday nights. You can even take a dip in their pool on the 19th floor and watch Chicago from above.
Friday Night
We got to our hotel around 6pm, not much time for activities but we made the best out of it. We started walking to DuSable Bridge for some amazing Chicago River pictures and views.
The Bridge is located next to one of Chicago’s most popular Deep Dish Pizza places Lou Malnati’s. They have several locations, this one is in the basement and has a very cool ambiance. After dinner we decided to go for some drinks at LondonHouse Chicago. It’s a Hotel with a rooftop bar with the best views of Chicago downtown. At this point it was dark, windy and cold so we had a drink at their indoor bar and live music.
We finished the night at a very local spot, called the Mother Hubbard’s Chicago. There were pool tables and the music was jumping. It definitely was a spot where lots of friend groups got together to get the night started. Since this was our first night and we had big plans for the weekend, we went home before midnight to get a good night sleep.
Saturday
Of course we had to start our day at the Millennium Park and the world famous Bean. Getting our cute couple pictures was tough as several thousand other tourists had the same idea. Did you know the official name for the Bean is actually “Cloud Gate” and it was installed in 2004 by artist Anish Kapoor?
We kept on walking as the Millennium Park turns into the Grant Park and home of the Lollapalooza Festival. We stopped at a food cart and got some elote in a cup. It is called esquites, and is basically corn, mayonnaise, butter, Mexican spices and Mexican cheese. It is so delicious and worth the stop!
At Grant park, you can find the Buckingham Memorial Fountain, which became famous during the intro of ‘Married with Children” sitcom in the 90s. Be aware, the fountain was still not running as it was still too cold in April.
We then headed to a different neighborhood called Wicker Park. We ate Brunch at a newly announced Michelin star restaurant “Kasama Chicago“. Here is a tip. At night the menu at Kasama is about $150 a person, but the brunch is only about $15-25 and you can just walk in to get delicious pastry. It’s a Philippine-fusion restaurant and the food was just so amazing. We were so happy to get the Michelin star experience without the price tag.
We then walked around in Wicker Park and visited various boutiques and a super cool rooftop bar called Whiskey Business. It’s a colorful vibrant bar with some amazing cocktails, a huge variety of cocktails and super fun rooftop. After exploring Wicker Park and having a couple drinks, we went back to the hotel to get ready for the night.
We made reservations for 615 for an Architecture Boat Tour. We used Viator which seemed the be the easiest way to book a tour in advance, plus their cancellation policy is very flexible. The 1.5 hour boat tour at sunset was just spectacular! Stunning views everywhere you look. There is also a full bar on board the tour guide knew so many amazing facts about each building, we highly recommend exploring Chicago by boat.
We also bought comedy tickets for Second City Comedy club in Old City for 10pm. We picked an Italian place for dinner called Gussie’s. The place is famous for handmade Italian pasta and their incredible delicious bread that is served to each table. The bread was stuffed with cheese and herbs and drizzled with oil. We never tasted anything like it and are so happy we picked Gussie’s.
After dinner we headed across the street to see the The Second City’s 110th Mainstage Revue, which is their main show and a mix of prepared sketches and improv. Wow, we had so much fun at Second City! We didn’t know what to expect, but all I can say, it makes now so much sense that so many talents will end up on SNL. We even sat behind a former SNL alumni, Chris Kattan.
Sunday
Our flight was at 6pm so we have a fair amount of time to explore some more of the Windy City! At this point we did not have an original Chicago Dawg, so what better way to end our trip with a 70 years old original Hot Dog place called Mister J’s Dawgs and Burgers. The hole-in-the-wall place is situated between modern architecture in downtown Chicago and it made our hearts so happy to see an original place surviving all the changes Chicago has been through.
After eating our dogs, we walked along the Michigan Lake promenade to explore the Navy Pier. The Navy Pier is home of some restaurants and a huge Ferris Wheel. I would argue the best full skyline pictures can probably be taken there. On our way back to the hotel to pick up our luggage, we came across a really cute place called Pinched on the River. It’s located on a little canal and gave us Amsterdam vibes. We highly recommend to stop by in this cute area for a drink.
This is a full packed itinerary and we did not have time to visit museums and the aquarium, both of us have done those before. I would say, if you only have 2 days, just follow this itinerary. If you have 3 days, pick a museum that is important to you. I also recommend coming from May through October, because it was still cold and windy in Chicago, luckily we packed for the weather, but it might be more fun in the summer when the roof tops are packed and the parks are green.
Below is a summary of our fantastic weekend itinerary. I hope you enjoy it! Please Tag me, email me and message me if you do anything on this list. I would love to hear from you all.
Friday:
- DuSable Bridge
- Deep Dish Pizza at Lou Malnati’s
- Roof top drink at LondonHouse Chicago
- Night Cap at another Hubbards
Saturday:
- Millennium Park with the Bean and Buckingham fountain
- Explore Wicker Park
- Architecture Sunset Boat Tour
- Comedy show at Second City
Sunday:
- Brunch in Downtown Chicago
- Navy Pier
- Pinched on the River
If you enjoyed this itinerary and are planning to do any of those items, please tag Stepke_adventures in your Instagram posts. Feel free to provide any feedback below.