Getting away with a group of friends is always a blast! We love going into the city and having fun! This option is mostly center around downtown. Mostly everything is within walking distance! Check out some things we like to do or want to do!!
Drop of your bags at the front desk at The Westin Chicago River North, then Uber to Wrigley Field. You could also take the CTA Red Line to Wrigley if you don’t want to deal with traffic. You just need to walk about 6 blocks from your hotel (CTA Red Line (State Street Subway)), and it takes you basically to the field by the bleachers entrance. We like to go to day games because then we have the evening free. Once at Wrigley, find your seats, grab a beer and enjoy! We of course can’t go to the ball park without getting a hot dog … they are sooooo good! Pork & Mindy’s is also pretty ahhhmazing! It’s Jeff Mauro’s restaurant in Chicago. The Bao to the Pork and the Pig Candy BLT are what I recommend!
Uber back to downtown. I suggest officially checking into your hotel first, and change for dinner. Sweetwater Tavern and Grille is one of my favorite spots for dinner and a drink. I would suggest making reservations for 6pm. I love their pan fried tilapia and their grilled asparagus is divine! Their French Kiss and Peach Cooler cocktails are delicious in the summer as well.
After dinner head to Howl at the Moon for a fun night of dueling pianos and drinks! We LOVE Howl at the Moon. It’s one of our favorite places to go with friends. It does get crowded quickly and tables are hard to find if you show up much past opening on the weekends. I would either reserve a table or get there as close to 7 as possible. (You could also skip Sweetwater Tavern, and show up at 7pm for dinner there. That would beat the crowds as wel
If you can all decide on a bucket flavor, I suggest ordering one! We got a bucket, as well as other drinks / shots one of the times we went and spent close to $150 just on drinks! LOL I like the Sex on the Moon and the Pink Paradise. The best thing is that Howl at the Moon is only a 3 minute walk from your hotel!
Sleep in a bit!!! Get ready and head to breakfast at Yolk-Marina City around 9:30. (It’s a minute walk from your hotel!) This breakfast restaurant comes highly recommended! Seriously their menu looks amazing; I want to order a little bit of everything!
After a fulfilling breakfast, head to Magnificent Mile for some shopping! Some of our favorites to stop at: Eataly, Nordstrom Rack, Saks Fifth Ave, and Water Tower Place.
For lunch, book a walking food tour from Chicago Food Planet. This is the best of both worlds! My favorite tour would be the Classic Gold Coast Old Town one. You learn about some history of Chicago, while getting to try some of the best foods! This tour takes about 3 hours, but it’s so fun!
Head back to your hotel to change for the evening. Walk to the 360 Chicago Observation Deck for some awesome city views! Around the corner is the rooftop bar, Drumbar. I love rooftop bars, and this one looks so enticing! I want to try their Chamomile Ketel Soda!
For some entertainment head to Navy Pier in their Miller Lite Beer Garden. The views are gorgeous and in the summer they have live music!
Make reservations for Quartino Ristorante at 7:30. This place is a delicious Italian restaurant with plates you can share! They are also known for their wine selection. Enjoy a night of relaxation, food, and wine!
Wake up and drop your bags off at the front desk. Walk to Cupitol Coffee and Eatery at the Streeterville location. The restaurant itself looks cozy, and their breakfast offers a great variety. I love that they offer organic cold pressed juices for a healthier option, especially after all the food you’ll eat the day before!
After breakfast, walk to Oak Street Beach for an hour paddle board lesson! All that balancing (or in my case falling!) is bound to make for some fun memories with friends! Soak up some sun on the beach before heading back to the hotel to grab your bags and head home. If you’re feeling up for it, stop at Ghirardelli Ice Cream and Chocolate Shop. It’s on the way back to your hotel, and it’s the perfect end to a fun getaway.