Planning the perfect 3-day Chicago itinerary can be a thrilling experience. With so much to explore, having a well-organized plan can help you maximize your visit while still allowing for some spontaneous adventures. This guide offers a comprehensive itinerary for first-time visitors to Chicago, covering top attractions, dining spots, and travel tips.
This trip was quite an adventure for us! We deliberately chose not to research our journey (well, I didn’t; Daniela couldn’t resist). I love the thrill of discovery, while she prefers to be well-prepared. Our different approaches create a perfect blend I like to call “organizational chaos” (lol). Daniela’s research provides a framework of ideas, while my lack of preparation allows me to experience what I call the “Virgin Eye” perspective. I cherish seeing things for the first time.
Though I’m not that old, I do remember the days before the Internet when we relied on maps and asked for directions. So, even though Daniela has excellent suggestions, I often have to ignore her previews to preserve the element of surprise. This dynamic makes our trips interesting… LOL… okay, enough digression. Here it is, ready for you: the ultimate 3-day Chicago itinerary for first-time visitors!
HOW TO GET AROUND CHICAGO EFFICIENTLY
Navigating Chicago can be challenging, but with the right tips, you can get around with ease. STICK WITH PUBLIC TRANSPORTATION. SAY NO TO CAR RENTAL! Why?
• Parking is outrageously expensive (I’ll share some tips in this article).
• There’s an abundance of bus and train options.
• Taxis are reasonably priced, and Uber and Lyft can be even cheaper.
• Hop-On Hop-Off buses are a great way to get around town if you time it right.
TOP TRANSPORTATION OPTIONS IN CHICAGO
Chicago offers various modes of transportation, each with its advantages.
• CAR RENTAL
A great way to cover more ground, though parking costs add up quickly. Daily rental rates are reasonable, but you might spend $25-$75 per day for a standard/full-size vehicle, depending on discounts and rental status.
• BIKE RENTAL
Economical and convenient for city travel. Divvy Bikes are the most accessible, but you can find cheaper deals on Groupon-type sites from local businesses. Expect to pay $10-$20 per person for day rates.
• SUBWAY
Prices vary, but the most cost-effective option is an all-day pass. Options range from $5 for a 1-day pass to $75 for a 30-day pass. The L train from O’Hare has separate fares, but discounted rates are available with a Ventra transit account ($5 for setup or a single Ventra Transit day pass from kiosks).
• BUS
Fares are the same as the subway, and passes are interchangeable between bus and train systems.
• TAXI
Base fare is $3.25, with an additional 25 cents for every 36 seconds and $2.25 per mile. A typical fare from O’Hare to downtown is around $30-$40.
• UBER / LYFT
Prices are similar to taxis, though they vary based on demand and time. Taxis offer a standard rate, whereas Uber and Lyft rates fluctuate.
• WALKING
If you’re able-bodied, walking is the most economical option once you’re in the city.
NAVIGATING CHICAGO’S PARKING SCENE: (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.
Here are top sites offering substantial deals on both overnight and daytime parking, often at a fraction of the standard rates:
• 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—This great app shows the prices of many nearby locations and where street parking is available.
• Parkchicago.com —This is metered parking; depending on the location, you can refill your time on the fly in upwards of 6-10 hours, and 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) – $139 or CHICAGO C3 (3 tickets/attractions) – $102.
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 30+ attractions/experiences). This will give you more bang for your buck if you want to tackle more attractions for a fraction of the cost. There are 2 options: All- Inclusive Pass starting at $124 (Visit as many attractions as you like over 3 days) or Explore Pass starting at $84 (visit 3 attractions of your choice.)
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: Evening Arrival
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: Lou Malnati's
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: Exploring the City
Morning: Millennium Park and Magnificent Mile
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: Oasis Cafe
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: Willis Tower and Skydeck Ledge
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: Xoco
Mexican food at Xoco. Delicious eats! We filled up on: The Cubana, Guacamole & Chips, Chicken Tinga.
Day 3: Final Adventures
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.
Morning: 360 Chicago & Museum of Contemporary Art
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.
Lunch: Friends Sushi
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 skipped dinner)
Afternoon: Lincoln Park Zoo and Navy Pier
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: Last-Minute Activities
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.
Morning: Pilsen District
We drove to the Pilsen section of Chicago. This district has amazing wall art. You will definitely enjoy walking 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, and Chicano art and history.
Lunch: Don Pedro Carnitas
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: Chinatown
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.
FAQs
What are the must-see attractions in a 3-day Chicago itinerary? The must-see attractions include Millennium Park, Willis Tower, and 360 Chicago.
How can I save money on transportation in Chicago? Use public transportation, bike rentals, and apps like Parkwhiz for parking deals.
Is a CityPass worth it for a short trip to Chicago? Yes, a CityPass can save you money and time if you plan to visit multiple attractions.
Where can I find the best deep-dish pizza in Chicago? Lou Malnati’s Pizzeria is highly recommended for its delicious deep-dish pizza.
What’s the best way to get around Chicago without a car? Public transportation, including buses and subways, is the best way to get around without a car.
Are there any free attractions in Chicago? Yes, attractions like Millennium Park and the Lincoln Park Zoo are free to visit.
We hope this 3-day Chicago itinerary helps you make the most of your trip. Have tips or questions? Share them in the comments below or tag us on social media!
