This post is in sponsorship with Fairmont Chicago. All opinions are my own.
It may seem jaded at this point to talk about how exciting it is for me to travel on my own to so many cities after 3 years, but Chicago truly captivated me the minute I arrived. Although Chicago is called “The Windy City,” I say that their culture, food, and amazing architecture are what makes this city stand out from the rest. Because the city has over hundreds of attractions, one might ask themselves, “Where do I begin?” Thanks to the opportunity to have my trip hosted by Fairmont Chicago, I’m happy to share with you a comprehensive Chicago travel guide of places to see, explore, and eat. Plus, I also include travel tips that are important to know for any female solo traveler. Let’s begin!
Solo Travel Girl’s Guide to a Weekend in Chicago
Airport and Transportation Tips
Now that you’ve booked your flight, where do you go once you arrive? It’s important to know different ways you can get to the city.
For me, a practical and cheap way to get to the city when you’re arriving from Midway Airport is to take the CTA. Follow signs that direct you to the CTA/Train transit, which will lead you to a indoor walkway that is located outside from the airport. For 1 adult one-way ticket, it’ll only cost $2.50. Once you get inside the train, it’ll take you 15-25 minutes to arrive at the last stop: Roosevelt Station. Depending on where your hotel is located, I would figure out which station is most convenient for you to stop, however, Roosevelt Station will bring you to central Downtown Chicago. I believe the CTA is safe for you to ride, especially if you’re riding it during the morning or afternoon, but always be precautious about your belongings at all times (no matter what time of day).
If you prefer not to deal with the hassle of public transportation, Midway Airport does allow you to have Uber, Lyft, and Taxi Services to pick you up from the airport to drive you to the city as well. Depending on the traffic, it can cost you around $25 to go to Downtown Chicago in 20-30 minutes.
Where to Stay
If you’re traveling solo, I would personally look for a hotel that is centrally located to a lot of great restaurants, parks, and sightseeing landmarks. Fairmont Chicago is a great choice for first-timers, especially if you want to indulge yourself in all the fabulous amenities they have to offer. The hotel provides a luxury spa, bar lounge that serves breakfast, snacks, lunch, and dinner, as well as a club lounge that is perfect for mingling with staff and other guests. For a single king sized bedroom, it provides:
- Huge wide screen TV
- Bathroom area that includes a separate toilet area, bathtub, and shower room
- King Sized bed with a stylish floral bed frame
- Office/Desk area
- Free Wi-Fi
- Sitting/Living Area
- Tall Closet that includes floor length mirror, iron and ironing board, a safe, hangers, and an umbrella
- Refreshment Area with a coffeemaker
What I loved most about this hotel is that there is no hassle when it comes to traveling on my own agenda. The top sightseeing places, such as Magnificent Mile, Millennium Park, Cloud Gate, Buckingham Fountain, Chicago Theater, and Chicago Riverwalk are all within walking distance from Fairmont Chicago. Plus, the staff are also really helpful with travel spot recommendations as well! During the day, if I ever needed to rest, I could easily return back to my hotel for a break until I resume exploring the city again. If you want to learn more about Fairmont Chicago, click here.
Where to Eat
Columbus Tap: N Columbus Dr, Chicago, IL 60601
Conveniently enough, I had the pleasure of dining at Columbus Tap, which is a posh restaurant and pub located inside Fairmont Chicago. Not only is the ambiance of the restaurant very welcoming, but the food makes you want to stay here all day! If you dine here, I personally recommend starting out with the Fromage Board as an appetizer, then order the Tap Burger or Bucatini Pasta as the main dish, then finishing off your meal with any of their desserts! In their drink menu, you can also order a Flight of Columbus Tap Selects where you can drink local Chicago beer. For a refreshing non-alcoholic choice, I also enjoyed tasting the Garden Grove, which has a minty citrus taste. You can view their menu here.
Portillo’s: 520 W Taylor St, Chicago, IL 60607
If you want to try casual, authentic Chicagoan food, then Portillo’s is a popular choice for both locals and tourists. The restaurant has a fun, cafe-style look that has tons of signed photo frames decorating the walls with celebrities, sport players, and local communities snapping a photo with their Portillo food. If you’ve never tried, I loved tasting their Italian beef sandwich paired with their crinkle cut fries. Learn more about their food here.
Little Goat Diner: 820 W Randolph St, Chicago, IL 60607
If you want to explore your taste buds a bit, then the Little Goat Diner is the perfect restaurant for you. First off, their menu will make you LOL with their witty menu items that include “THIS LITTLE PIGGY WENT TO CHINA” and “EVERYTHING IS EVERYTHING CRUMPETS.” While they serve breakfast, lunch, and dinner, I think that their breakfast food items are worthy of eating during any time of day. I recommend trying their Bull’s Eye French Toast – the combo of strawberries, crispy chicken, and BBQ sauce is mouth savoring! Check out their menu here.
Giordano’s: 130 E Randolph St, Chicago, IL 60601
Lastly, if you want to taste the ever-popular deep-dish pizza, I think that Giordano’s is a convenient and super popular pizzeria to dine at! Ordering your own individual deep dish pizza with custom toppings is a perfect size for one person, however, there are so many types of pizza to try in their menu! You can also order pasta, sandwiches, and salads at Giordano’s if you’re curious to try out their other menu items.
What to See for Free
Trust me when I say that there is so much to see while you’re in Chicago! With over hundreds of attractions, there is a never-ending amount of places to explore. Depending on the time of year you’re visiting, I would make sure that you’re dressed for the occasion when visiting some of these sightseeing spots. Weather aside, here’s a rundown of the top free places I recommend any female solo traveler to check out (and take fun tourist shots):
Parks
Millennium Park: 201 E Randolph St, Chicago, IL 60602
A contemporary designed public park with lots of walkways and fun places to do outdoor activities.
Lincoln Park: 2001 N Clark St, Chicago, IL 60614
A shoreline park, located in a neighborhood district, that includes a zoo, garden arboretum, and tons of fountains.
Grant Park/Buckingham Fountain: 331 E Randolph St Chicago, IL 60601
Small, but charming historic park that includes the Buckingham Fountain
Scenic Ocean/River Views
Chicago Riverwalk: Chicago Riverwalk, Chicago, IL 60601
Long walkways and bridges with a great combination of river and city views – great place for boat tours!
Navy Pier: 600 E Grand Ave, Chicago, IL 60611
Great views of the Michigan River and city skyline with tons of eateries and carnival attractions!
Gardens/Greenery Spots
Crystal Gardens: 700 E Grand Ave, Chicago, IL 60611
Small, but charming garden arboretum with lots of tall palm trees
Lincoln Park Conservatory: 2391 N Stockton Dr, Chicago, IL 60614
Huge variety of plants and flowers located inside with beautiful walkway views
Art Installments
Cloud Gate: 201 E Randolph St, Chicago, IL 60602
Iconic landmark that is also known as “The Bean” – perfect for photo ops!
The Honeycomb: 2121 N Stockton Dr, Chicago, IL 60614
Very elegant landmark that overlooks the Lincoln Zoo
Let me know what you guys think of my Chicago travel guide! Have you been to any of the places I’ve mentioned? Make sure to let me know by tagging me in your photos. I also want to thank Fairmont Chicago and Columbus Tap for hosting my stay and making me so welcomed in the city! If you’re interested, you can get the opportunity to stay at Fairmont Chicago with a special offer here. For more of my travel content, be sure to follow me on all of my social media. Until next time!
Wow, this is such an amazing travel guide! I’m going to Chicago next week and I will need to check out the Honeycomb! Thanks for making this post – it’s super helpful!
Your photos are so mesmerizing as always, Reesa! Love your photos and I’m so surprised at the amount of places you’ve seen in a short amount of time! You always go above and beyond for your readers and we appreciate it!
This is great.
Keep it up.
Love your blog.😍