Ok, this was an interesting trip. We purposely didn’t research this trip (Ok, I didn’t. Daniela couldn’t help herself). I enjoy the discovery process, while she, on the other hand, enjoys being prepared. The different way we approach trips creates a perfect synergy which I call organizational chaos (lol). Her research gives us an idea of what to do; my lack of research allows me to enjoy what I call the “Virgin Eye” experience. I enjoy seeing things for the first time. I am not that old, but old enough to remember there was a day when there wasn’t the Internet, the days we relied on maps and spoke to people for directions. So, even though Daniela had great ideas, I always have to tune out everything she wants to show me about places we were planning to visit. This makes for interesting trips… LOL … ok, no more tangents… Here you go, ready for you, the perfect 3-day itinerary in Chicago!
A Few Things to Know...
First things first (things I found out the hard way, you can decide whether to do this or not). STICK WITH PUBLIC TRANSPORTATION. SAY NO TO CAR RENTAL! Why?
• Parking is insanely expensive (I have tips which I will add in this article).
• Bus and Train transportation in abundance.
• Taxis (relatively fare priced even cheaper with Uber and Lyft).
• Jump on/off tourist buses, If you time it properly, you can definitely use them to your advantage to get around town
HOW TO GET AROUND IN CHICAGO
Like the Basic food Groups, there are basic modes of transportation:
• Car Rental – Great way to cover more ground; though daily rates are fairly priced, you add up costs looking for parking. Depending on your rental status and discounts, you could spend 25-75 dollars daily for a standard/full-size vehicle.
• Bike Rental – Economical and convenient. An excellent option for getting around the City. Divvy Bikes is the most accessible, but you can find cheaper deals constantly on Groupon-type sites for independent struggling-to-survive businesses. Look to spend 10-20$ per person for day rates.
• Subway – Price varies, but the cheapest route is getting an all-day pass for the time you are there (Choice of 1/3/7/30 day passes). The cost ranges from $5 for a 1-day to $75 for a 30-day pass. There are separate fairs for the L train from O’hare, but they are also discounted fares if you have a Ventra transit account (5 dollars for the account setup, but you can get a single Ventra Transit day pass from one of the kiosks that sell fares)
• Bus – See Subway. Fares are the same for both Bus and Train systems. Passes are interchangeable.
• Taxi – Base fair (jumping into a cab) is 3.25, then it is 25 cents for every 36 seconds and 2.25 for every mile. Base fare from Ohare to downtown is around $30-$40
• Uber/Lyft – Used to be cheaper, but prices are relatively the same. Taxis win on having a standard rate, while Uber/Lyft types are based on demand and time.
• Hoofing It – After you make it to the City, not a bad option. It is the most economical of all of them if you are able-bodied enough to do it.
PARKING IN THE WIND CITY: (for the lovers of driving)
Understand paying the total price for daily parking can start to add up, even if you are on a work trip, itemizing your expenses. Full-price day rates, some without in/out privileges, can go as high as $80 a night! (What, what, what!?!?!?) Yes, it is wild. Daniela laughed as I couldn’t find parking and almost cried when I asked what the day rates were (they would come out to more than the rental cost!). Her enjoyment in insinuating “I told you so” was piercing to the soul because she prepped, but guess what, YTF fam? I went old school and used my gift of gab to find out some information for us car renting hard heads.
Best sites that provide ample deals for overnight and during-the-day parking (at a fraction of the full price cost).
• Parkwhiz.com – This can be used everywhere. It shows you deals in your vicinity, which you can purchase through the app and show the attendant.
• Spotangels.com – Great app shows the prices of many locations nearby as well as shows you where street parking is available
• Parkchicago.com – This is metered parking; you can refill your time on the fly, depending on the location, in upwards of 6-10 hours which you can pay from your phone.
SIGTHSEEING IN CHICAGO
Which Chicago Pass is Best?
If you are planning to visit multiple attractions, passes can be a great way to save money! You have two options in Chicago: CityPass and GoCity. This is on preference but Your Travel Friends Recommends going with GoCity.
A brief overview of passes. You decided what works better for you:
CityPASS – You can opt for CHICAGO CityPASS (5 tickets/attractions with Premium Admission) – $134 or CHICAGO C3 (3 tickets/attractions) – $96.
These are the attractions you can choose from:
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Shedd Aquarium
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Skyjack Chicago
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Field Museum
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Art Institute of Chicago
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Museum of Science and Industry
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360 CHICAGO Observation Deck
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Adler Planetarium
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Shoreline Sightseeing Architecture River Tour
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Centennial Ferris Wheel at Navy Pier
GoCity – With this pass you can choose among 29 attractions/experiences). This will give you more bang for your buck if you want to tackle more attractions for a fraction of the cost.
With the GoCityCard, all these attractions are available to you:
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360 Chicago
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Skydeck Chicago
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Shedd Aquarium
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Hop-on Hop-Off Big Bus Chicago
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Architecture River and Lake Tour
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Lakefront Speedboat Tour
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Extreme Thrill Ride
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Navy Pier Ferris Wheel and Rides
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Field Museum
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Museum Of Science and Industry
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Adler Planetarium
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10pin Chicago 90-minute Bowling & Pizza
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The Forge Adventure Park
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Chicago Children's Museum
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Chicago Pizza and Drink Combo
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Legoland Discover Center
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Downtown Chicago TV & Movie Sites Walking Tour
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Chicago River Architecture Walking Tour
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Monsters and Haunted Mysteries of Chicago Walking Tour
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Two-hour Bike Rental by Bike and Roll Chicago
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$20 Food and Drinks Credit at the Cauldron Chicago
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Museum of Contemporary Art
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Chicago History Museum
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Frank Lloyd Wright Home and Studio Tour
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Chicago Theatre Marquee Tour
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American Writers Museum
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Robin House
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Lincoln Park Zoo Rides
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Ernest Hemingway Birthplace Home
As you can see from the availability and options above it would be difficult not to choose GoCity. But as always the choice is yours (this is coming from the guy who persisted to rent a car when he shouldn’t).
One thing you may notice is that GoCity doesn’t appear to offer the speed line. Ok, this is completely on preference, but from our experience using both speeds as well as regular lines, the difference is small (15 minutes max). If you get there early the lines are just as fast as the speed lines. So this choice is completely up to you.
The Perfect 3-Day Itinerary in Chicago
Day 1 (Night):
We arrived on a late flight, picked up our rental (don’t laugh!), then proceeded to check in at the Hotel Chicago (a must-stay, right across from the House of Blues and next to 10pin (a unique Bowling Lounge).
Dinner: You’re in Chicago, so what do you think we ate?!?!? Deep dish pizza, aka Chicago-style pizza!! There are tons of places to get a deep-dish pizza. Lou Malnati’s Pizzeria indeed backed what the reviews stated. Their deep-dish pizza was bites of deliciousness. Definitely a YTF stamp of approval!
Day 2:
MORNING:
Breakfast at the Hotel (sorry, no breakfast tips in this review, Hotel Chicago had great breakfast spreads and since it was included in our rate we took advantage of it.
We headed to Millenium Park for a pic opt but found out that getting there at 10 am was a little too late (already crowded). We continued to the Magnificient Mile and browsed the stores as we enjoyed seeing how colorful this city is.
LUNCH:
We were in the mood for grape leaves and found a nice hidden hole in the wall called Oasis Cafe (note: they share their space inside Wabash Jewelers Mall, so you have to walk through the little mall all the way to the back to get to the seating area/counter).
We Tried: Wabash Mixed Combo, Hummus, Vegetarian Falafel Sandwich, Grape Leaves were sold out :(.
AFTERNOON:
We checked out the Willis Tower to enjoy the view from Skydeck Ledge.
YTF advice:
• There are four ledges; the two ledges around the corner from the entrance may have shorter lines, so check before you stand on the 1st set of lines you see!
• No Need for Fast track if you purchase tickets online (extra wait time: 15 mins)
• Fast track only bypasses Line 1
• The second line (history of the towers). Think of it as a break from standing.
•There is no FAST Track or priority up to the top! So save your money if you like.
Your Travel Friends Recommends: If you are not using GoCity, purchase your tickets online and shave an extra 45 mins to an hour to get to the top.
DINNER:
Mexican food at Xoco. Delicious eats! We filled up on: The Cubana, Guacamole & Chips, Chicken Tinga.
Day 3:
Your Travel Friends Recommends: This is for the brave or the early risers! Check when sunrise happens and hopefully it is a clear day, you will be in for a treat if you head over to Millennium Park, pics of empty Chi-Town streets, or head to the Adler Planetarium to capture great city view pics.
BREAKFAST:
Sorry guys, the food at our hotel was delicious and hit the spot…oh did we mention free? You can’t beat free. (YTF Motto: If it’s free, it’s for me! LOL!)
MORNING:
360 Chicago – Go all the way to the top and enjoy the view. You can also grab a bite to eat and relax from the top. Depending on your level of fear, for an extra 7 dollars, you can go on the Tilt. Basically, it is exactly what the word states, you tilt forwards thousands of feet up in the air and hope that today is not the day the window mechanism decides not to giveaway and you fall to your… ok, ok, ok, I will stop being so dark, but it was fun!
Your Travel Friends Recommends: Take turns going on the tilt, they don’t allow you to take pics while on the Tilt since this is how they make their money, but you can easily take a picture from the side of the skywalk of whoever is on the ride first. Also, I believe the best and free view at 360 Chicago is in the women’s bathroom in the Signature Lounge (I swear I didn’t sneak in to see for myself…” I heeeaaard it was the best view”). It is a free elevator ride and you don’t have to pay any fee to use the bathroom. Sorry guys, no windows in the men’s room, pretty boring we lost on this one, though we will always have the fastest lines to use the bathroom!
Museum of Contemporary Art: Depending on the exhibits this can be a hit or miss, for Daniela this was a hit since it showcased a prominent ballet choreographer. The entry fee is $22 per person. For residents, it’s free on Tuesdays, as well as free for Bank of America bank or credit cardholders. If you are a teacher or student they also give you a discounted price. (Hint: We are all students or teachers of something! So don’t forget to say that! 🙂
LUNCH:
Daniela was in the mood for Sushi so nearby there was a place called Friends Sushi. Decent-priced, middle-of-the-road dishes. Great attentive staff (though when we went, it was semi-empty). We then went for another walk and ended up at Portillo’s where we got a hot dog with everything on it and then to make matters worse we fell in love with popcorn from Garret! (yep, we are skipping dinner)
After our extended lunch, we headed over to Lincoln Park to check out the Lincoln Park Zoo. Afterward, we walked around Old Town. Once it started getting dark, we headed over to the Navy Pier.
Note: Parking starts at $18 for 1 hour ; valet parking is also available if you dine at certain Pier restaurants. Check with the respective restaurants to see what deals are present, or visit the Navy Pier website.
DINNER:
Skipped. It was also late, and stores were closing early on a Sunday, but we found dessert!
Insomnia Cookies! You will enjoy just about anything there and also get the sugar energy you need for the late-night walk back to the hotel.
Day 4 (Morning):
This was our 1/2 day left before our flight back to NYC.
Yes, we decided to fill in every minute that we could and we got really lucky with our findings. If you have a late flight and want to fill in some more activities before heading back to the airport, try out what we did.
BREAKFAST: Yes you know what I am about to say, Hotel Chicago took care of us. Sorry, no breakfast tips this time. Next time we will have a few!
MORNING:
We drove to the Pilsen section of Chicago. We found amazing wall art in this district. You will definitely enjoy the walk around this culturally infused area. After the walk, we found the National Museum of Mexican Art. This is also a great spot in Pilsen to learn more about Mexican, Latino & Chicano art and history.
LUNCH:
Don Pedro Carnitas (YTF Hidden Gem Alert!). Ok, go somewhere else if you are looking for a fancy restaurant with great decor and proper lighting. If you want real, authentic (great-priced) Mexican food, you are exactly where you should be. YTF portion advice (1/2 lb is enough for two people) – If you can’t stomach authentic Mexican dishes, which include various body parts (ears etc.), you can ask for just white/dark/skin for their pork dishes. You can try the Barbacoa if you want to try their beef dishes. For sides, try their beans and their cactus salad (hint you can ask for a sample of their cactus salad and chicharron. A sample will be enough to satisfy your pallet). There is free parking on the side, if spots are available, or you can find street parking.
If you think Don Pedro is too “authentic” for you, you can take a walk to somewhere more traditional Honky Tonk BBQ two blocks away. We can’t recommend anything there since we fell in love with Don Pedro’s.
AFTERNOON:
We headed to Chinatown to quickly check out stores and look for any treats we could get. Since there wasn’t enough time to walk around, we must have a part two to Chi-town. Alas, time was up, and we headed to the airport.
Did you enjoy the perfect three days in Chicago itinerary? Please feel free to comment and leave recommendations on places in Chicago. Our community would appreciate it!
