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| View from Navy Pier |
There is so much to see and do in Chicago for little to no cost, and the ability to walk everywhere makes it even more inviting. You could spend weeks in Chicago trying to hit everything, but what if you only have, say, a weekend? What are the must-dos? And the better left don't's?
What's Ahead:
- Everything in this post is located in the Chicago Downtown Loop!
- Each is walkable from the other and from whichever hotel you choose to stay at within the vicinity!
- All can be completed in 2-3 days for a complete and total immersion into ChiTown!
- Stay tuned for my sample Chicago Travel Itinerary at the end!
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| Buckingham Fountain in Grant Park |
#1: Transportation
DON'T: Feel the need to rent a car. Just take a cab from the airport to your chosen hotel and walk from there. Parking is atrocious whether in the parking garage or anywhere you're trying to visit. If you're staying downtown, you can get almost anywhere by foot.
DO: Feel free to get a hop-on hop-off bus pass to help you get around if you're traveling across town.
Windy City Tip #1 - Walking in Chicago is definitely part of the experience, and it will surely help you get in those steps! Just be aware that the cab drivers are crazy, and cars will run you over if you don't walk across the crosswalk quickly enough, so if you're from the slower Southern states, know you will have to pick up the pace.
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| View from the top of a hop-on hop-off double decker bus |
#2: Skydeck
DON'T: Feel the need to do the Skydeck in the John Hancock Building. For the price you pay, dealing with the crowd to spend one minute in a glass box to take a selfie has never seemed worth it to me.
DO: Stay in a skyrise hotel. There is a huge range of hotel pricing downtown, so there is something to fit everyone's budget. Being a part of the skyline and seeing the city from above and below is one of the best perks of staying in downtown Chicago!
I can't recommend a specific skyrise to stay in right now because my favorite (the Carbide and Carbon Building) shutdown last year due to COVID-19 struggles, but thankfully, they have sold and plan to re-open sometime this year or next. This 1920's gold-encrusted Art Deco skyscraper has my heart!
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| Hopefully this piece of history re-opens to guests again very soon! |
#3: Tours
DON'T: Feel the need to have a tour guide while walking through the city. Everything is reasonably easy to find, and it's so much more fun if you discover the sights on your own. This way, it's your personal experience, as opposed to yours and 100 other people's.
DO: Take a Double Decker Bus Ride (the Big Bus is a hop-on hop-off bus line, so you can make your way around town while seeing all the sites)! The historic skyscrapers are worth the hype and definitely part of immersing yourself in ChiTown.
Windy City Tip #2 - Bring a jacket! Even if it's the middle of Summer, bring a sweater or a hoodie at the very least. They don't call it the Windy City for nothing!
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| This was late June. It was still windy enough to merit a thin hoodie! |
#4: Food
DON'T: Feel like deep dish pizzas, hotdogs with seven toppings, and Italian pastrami sandwiches are the only way to "taste" Chicago!
DO: Eat at the local diners to get a real sense of what it's like to be a Chicagoan, and the most important food recommendation I can give you is Smith & Wollensky's for one of the best steaks you'll ever eat!
Windy City Tip #3 - Be aware that in this busy city, people are bustling in and out of these diners all day long, so don't be surprised when the waitresses start cleaning up around you while you're in the middle of your meal. It may seem a little rude to newbies, but they are trained to get you in, fed, and out as quickly as possible. They know you are busy and have important places to be.
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| This 14-ounce Cajun-seasoned filet mignon at Smith & Wollensky's was to die for! |
#5: Millennium Park
DON'T: Skip Millennium Park.
DO: Know that you can do almost everything in this park for absolutely no cost!
Points of Interest in Millennium Park:
- Cloud Gate (better known as the "The Bean"): As one of Chicago's landmarks, this is a mesmerizing piece of art to see in person!
- Crown Fountain: A great one for the kiddos, this is a fountain you can splash in! It's a piece of art showcasing Chicago locals in such an innovative and interactive way!
- Jay Pritzer Pavilion: You don't even have to buy a ticket, as the shows here are free! Or you can just walk by and waft in the melody drifting up from the extravagant orchestras that play this magnificent bandshell!
- Picnics are a must in Millennium Park, and you'll definitely get in the spirit by seeing tons of locals lounging around on the lush grass, playing frisbee with their pups, or reading a good book in the soft breeze.
- Lurie Garden (full of 2.5 acres of seasonal blooms) also connects to the park, and the park hosts Chicago's largest outdoor dining venue at the Plaza at Park Grill (the food is the only thing not free)! You can even take the BP Pedestrian Bridge over to Maggie Daley Park for a fantastic kiddie park, roller skating trails, and massive rock climbing walls! There's literally something for everyone!
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| If you've ever wondered what the inside of the "The Bean" looks like... |
#6: Navy Pier
DON'T: Feel like you have to spend a ton of money at Navy Pier! With the food (there are local restaurants and the chain ones, such as Margaritaville and Bubba Gump), the shopping, the tours, and the carnival rides, you could spend a fortune, but you can also enjoy the aura of it for pretty much free!
DO: Ride the Centennial Wheel to get 360 degree views of Lake Michigan and the Chicago skyline. The beer garden with it's live music is also free of charge!
- For more info on the Navy Pier, check out their website! -
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| Centennial Wheel takes you up 200 feet in the air! |
SAMPLE ITENERARY:
Friday -
- Land at O'Hare International Airport
- Take a cab from the airport to your skyrise hotel
- Head to the Navy Pier for dinner, drinks, and a ride on the Centennial Wheel
Saturday -
- Eat breakfast at a local diner
- Head to Millennium Park for the day
- Eat lunch at the Plaza at Park Grill
- Hop on a Double Decker bus ride from Millennium Park for a tour of the city
- Hop off at the Chicago Riverwalk to walk to Smith & Wollensky's for dinner
- Hop back on the bus at the Riverwalk to catch a ride to Grant Park
- Hop off at Grant Park to see the Buckingham Fountain light show
- Hop back on the bus to get back to the closest stop near your hotel (or walk if it's close enough)
Sunday -
- Eat breakfast at the hotel or another local diner
- Check out of the hotel room
- Head back to the airport for your return trip home
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Thanks for reading Blue Sky Days! XOXO, Kyrstie.