Chicago in early October is not only festive with fall colors, but it is also a perfect time to plan an exciting weekend getaway and escape the lingering heat of the south. It's one of my favorite big cities, and was even more fun to explore with Michael for the first time! Plus we had our own personal tour guides: our friends Lauren (a second Lauren, yes we’re Lauren squared) and Cesar who both lived in Chicago before moving to Oklahoma. You can tell by the lack of coats that they thrive in the cooler climate.
Let's go through some of our weekend getaway highlights to help you plan your Chicago itinerary!
Chicago Itinerary: Weekend Getaway
Thursday
- Fly into Chicago Midway Airport (direct flight via Southwest)
- Lunch at Athena in Greektown
- Drop off bags at Airbnb in Wicker Park
- Pick up groceries from the Oslo Jewel Grocery store across the street
- Jack’s Pumpkin Pop Up near Goose Island
- Cocktails at Devereaux rooftop bar on the 18th floor of the Viceroy Chicago
- Wrigleyville, with a stop at Sluggers
Weekend Getaway Highlights
Athena in Greektown
Our journey starts at Athena in Greektown for a quick lunch. The atmosphere made you feel as if you were in a Grecian restaurant. Scanning the menu, they offered many authentic beer, wine, and food options. We would highly recommend a visit here!
Jack's Pumpkin Pop Up
Cesar and Lauren sent us information about Jack’s Pumpkin Pop Up the day before we left, and it just so happened to be walking distance from our Airbnb near Goose Island. Jack's had endless photo ops, games, and a corn maze, plus the most amazing apple cider donuts you'll ever taste!
Devereaux rooftop bar
The Signature Room, an iconic restaurant and bar at the top of the Hancock Tower, closed just a week before our trip after 30 years of service, so we pivoted and made reservations at the Devereaux rooftop bar on the 18th floor of the Viceroy Chicago. It was a perfect way to wrap up day one in the bustling city, surrounded by downtown’s skyscrapers with Lake Michigan peeking through and sparkling in the sunset.
Note: Devereaux is currently closed for renovations.
Friday
- Purchase Ventra card for the ‘L’ (Chicago’s metro system)
- Took the 'L' to Chinatown and had amazing rice noodles at Daguan Noodle
- Water Taxi back to downtown
- Millennium Park and The Bean
- Drinks at Cindy’s Rooftop
- Dinner at Gene & Gorgetti, an authentic Italian restaurant
- Big Mini Putt Club
Weekend Getaway Highlights
Getting around - Ventra pass for the 'L'
Taking the ‘L’ (Chicago’s metro system) throughout the weekend was super easy and a great way to get around. You can purchase a Ventra card inside one of the terminals. We purchased new cards for $5 and then loaded it with the three-day pass which costs $15.
Fun Fact: The "L" gained its name because large parts of the system run on elevated tracks.
Getting around - Water Taxi
For $6 one-way, the Water Taxi is a cheap and unique way to travel through downtown and see the city from a different view. There are three departure locations: Chinatown, Michigan Avenue, and Oglivie/Union. We rode it from Chinatown to Michigan Avenue.
The Bean
The Bean is an iconic tourist photo opp location and Michael was so excited to see it in real life! Sprinkles slowly turned into a drizzle as we walked to The Bean to find Grainger Plaza was under construction through at least the spring of 2024. We still got this pic in front of the gate though! It was also neat to see how they were protecting the sculpture while working.
Cindy's Rooftop
The rain started to pick up so we cut our walk around Millennium Park short to seek cover and cocktails at Cindy’s Rooftop, a bar located on the 13th floor of the Chicago Athletic Association across from The Bean. It wasn't on the original itinerary, but we all agree it was one of the most memorable parts of our weekend getaway! Cindy's had a cozy atmosphere, excellent cocktails, and spectacular views of Millennium Park and Lake Michigan as well as The Bean!
Indoor putt putt
After dinner at Gene & Gorgetti, Michael and I decided to head back to Wicker Park near our Airbnb. We stumbled upon an indoor putt putt bar called Big Mini Putt Club. Due to our competitive nature, we didn't take as many pictures of the inside as we should have, but we really enjoyed finding this spot!
Saturday
- Navy Pier
- Lunch cruise on Lake Michigan
- Michigan Avenue aka The Magnificent Mile
- Eataly Chicago
- The Charleston
- Late Night Date Night show at The Second City
Weekend Getaway Highlights
Navy Pier and lunch cruise
While there is a lot to do in Navy Pier, we decided to set sail on a lunch cruise that departed from the pier and sailed around Lake Michigan. Would not recommend this as a must-do if you planning a quick weekend getaway, but it was cool to see a pretty perfect Chicago skyline from the water.
Note: I booked through Fever and it caused some confusion with which ship I needed to get on and where I needed to pick up my tickets. Purchase your tickets through an actual cruise line versus this third party service.
Eataly Chicago
After walking around North Michigan Avenue aka The Magnificent Mile, Cesar remembered a great place called Eataly Chicago he used to go to. If you want a truly authentic Italian store and restaurant experience, here it is! Visitors can purchase groceries to take home, sign up for a wine class, or dine in at their restaurant and watch as they make fresh handmade dough for their pastas and pizzas. I got the Ravioli di Zucca, a daily house made butternut squash filled ravioli, and it was as if I was transported to Italy!
Tip: There is quite a long waitlist to get a table. Instead, look for the dining areas with open seating.
The Second City
That night we had two fun agenda items: Stop by The Charleston, a bar in Bucktown, then head to the Late Night Date Night show at The Second City. The Second City is where many comedians started their careers such as fan favorites Steve Carell, Chris Farley, Tina Fey, Bill Murray, and Amy Poehler. There are several different show options including the Late Night Date Night show, which started at 11pm and only cost $25 a ticket (plus fees).
The Second City venue.
Sunday
- Check out of Airbnb
- Giordano’s for Chicago-style deep dish pizza
- Fly home
Weekend Getaway Highlights
Chicago-style deep dish pizza
Our group couldn't not eat Chicago-style deep dish pizza so we hit up Giordano’s, a classic, but there are so many options. Let me know your favorite in the comments!
While it was a quick weekend getaway, we made the most of our exciting visit to the Windy City! Subscribe to get access to our free Chicago itinerary to help you plan your next weekend getaway to Chicago!