Over Labor Day weekend, I went to Chicago for the very first time with my roommates! An extended weekend ended up being the perfect amount of time for a getaway, and this trip gave me so much confidence in traveling without “real” adults. As someone who has never been to Chicago before, I was a little nervous about planning and executing everything on our own, but it was the perfect destination to explore with my best friends without feeling overwhelmed.
Why Chicago?
Chicago is an amazing choice for a weekend trip from the University of Missouri. It’s a six hour drive from Columbia by car and pretty budget-friendly. While there are endless things to do in the city, a three day weekend was perfect. You get to experience the city without getting burnt out from all the walking, shopping, eating and sightseeing.
Hotel and Transportation
My friends and I stayed at a hotel near the Chicago O’Hare International Airport, which is about 30 to 40 minutes outside of downtown. We stayed at a La Quinta hotel and shared one room with two full-size beds, which was a lot of fun and made the trip very affordable! Another huge plus was free hotel breakfast in the mornings.
From there, we took public transportation into the city each day. Chicago has an amazing public transportation system called the Chicago Transit Authority (CTA). Staying outside of downtown seems inconvenient, but taking the CTA was so much easier than I thought and made the trip much more affordable than booking a hotel in the middle of the city. We paid $10 a day to park at the CTA station and only $15 for a weekend pass to use the CTA as many times as we wanted. It took so much stress off us to not have to drive downtown and try to park ourselves!
Making the Most of a Weekend
Now for our actual itinerary! We arrived in Chicago around 1 p.m. on Friday and decided to spend our afternoon exploring the neighborhood of Wicker Park, saving the big downtown tourist spots for our full day on Saturday.
Wicker Park has a completely different vibe than the skyscrapers you think of in downtown Chicago. It’s filled with vintage stores, boutiques, coffee shops, restaurants and even a vintage photo booth spot called “The Strip Club.” By 5 p.m., we had shopped our way through Wicker Park, so we hopped back on the CTA toward the Riverwalk for dinner. We ate at Pizzeria Portofino, which was right on the river and had such a perfect vibe! The rest of the night we walked along the Riverwalk before heading back to settle into our hotel.
Saturday was our full day of exploring downtown Chicago! Once we arrived in the city, our first stop was The Bean, a massive bean-shaped sculpture in Millennium Park that reflects the city’s skyscrapers! It may be basic, but it is a must-do for first-timers in Chicago. From there, we walked down Michigan Avenue, got coffee and donuts, and headed across the river to shop down the Magnificent Mile. We mainly shopped for clothes, but I also recommend shopping for souvenirs if it’s your first time in Chicago. For dinner, we went to Portillo’s for Chicago-style hot dogs, which I would highly recommend.
My favorite part of the trip was next: a 45-minute architecture boat tour on the Chicago River. This was the only activity that we booked in advance, and we loved it. Our tour was at 6:45 p.m., which was the perfect time to watch the sun set and the city lights begin to glow. The skyline views were beautiful, and I loved learning about the buildings and architecture along the river. After the boat tour, we explored the streets of Chicago into the night. Another destination on our bucket list was the iconic, lit-up Chicago Theatre sign! The theatre sign, illuminated buildings and street lights lining the river gave the whole city such a magical energy. Traveling as a college girl, I was nervous about safety before going on the trip, but sticking together in bright, well-populated areas made me feel completely safe the entire weekend!
On Sunday, we decided to explore another neighborhood of Chicago called Gold Coast. This neighborhood has beautiful historic homes and is right by the Lakefront Trail and Oak Street Beach. I really enjoyed wandering the streets, walking along the beach and doing even more shopping. Our last stop was the Ambassador Gold Coast hotel, where we went up to the rooftop for incredible views of the skyline from up high. We left the city around 2 p.m. to get back to Columbia at a reasonable time.
Why You Should Take a Trip!
Over the course of this weekend, my friends and I had the best time taking endless pictures, eating good food and exploring a new city together. You don’t need a huge budget or an entire week off to make memories with your friends! If you’re planning your own weekend trip, here are a few things I wish I knew:
- Research not only places to see, but places to eat too. Picking restaurants last minute was hit or miss for us.
- Don’t rely on AI to plan the whole trip. It led us astray a few times, especially when it came to navigating CTA stops and picking restaurants.
- Wear comfortable shoes! You’ll be walking a lot each day, so prioritize comfortable shoes over fashion.
- Don’t be afraid to explore different neighborhoods around the downtown area! Spots like Wicker Park and Gold Coast show even more of the city’s charm.
If you’ve been waiting for a sign to plan a girls’ trip with your friends, this is it! Chicago is the perfect college girls’ trip.