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Ultimate Guide to Chicago


There’s so much to discover in Chicago. Want to know about transportation, activities, lodging, food, and all that good stuff? Look no further. Here is my ultimate guide to Chicago.

How to Get Into Chicago

There are three airports in Chicago: O’Hare International Airport, Chicago Midway International Airport, and Gary Chicago International Airport. The two most popular are O’Hare and Midway. The two biggest differences between the two are the busyness of the airports and their proximity to downtown Chicago. O’Hare is one of the busiest airports in the world, with notoriously long lines. Midway is a little closer to downtown than O’Hare is, but both have good transportation options from the airport to your lodgings.

There are also other options for transportation to Chicago, including bus and train. Greyhound buses run regularly to Chicago for a fair price. From Detroit for example, you can get a $15 ticket. You can take a train into the city through Amtrak, too.

How to Get Around Chicago

The best deal for transport within Chicago is the Ventra Transport Card through Chicago Transit Authority. The Ventra card allows you to take unlimited transportation within the city by bus or train. You can do a day pass for $10, but I chose to get the $33 week pass, since I was there for five days. Another option is the Metra, which is a train (sort of like an above-ground subway) that takes you all over the city.

Other options include single-ride fares (for a bus, this is about $2.50) and taxi services. Uber and Lift are both popular and safe options for people traveling through Chicago. You can also go with an old-fashioned taxi cab.

Must Do in Chicago

  1. Chicago Boat Architecture Tour. This is a pretty cool boat tour that takes you around the city and teaches you interesting facts about the buildings. There is a ton of history about them that I didn’t know! It’s a great overview of Chicago. I took the Signature Lake and River Tour, and it was a lot of fun.Chicago Boat Tour
  2. Art Institute of Chicago. I spent almost 3 hours here! There’s a ton of South East Asian Art, Greek Art, Indian Art, American art, and pretty much any kind of art you can think of. The place itself is really interesting. I got lost just exploring the museum.must-see-in-chicago-karlaroundtheworld-4
  3. Skydeck on John Willis Tower. This is a fabulous, 94th-floor observation deck. I went on a weekday when there was hardly anyone, which was nice. It was during sunset, which was absolutely beautiful. I stayed awhile and waited for night, too, so I could take some night shots on my phone. Chicago comes alive at night, and it’s mesmerizing to see it happen. Chicago looks different during daylight, sunset and night—it’s so worth it to experience all three. Alternatively, you may book your Skydeck tour here.skydeck-sears-tower-chicago
  4. Grant Park is pretty much the center of outdoor life in Chicago. It includes such attractions as Buckingham Fountain (one of the largest in the world), a beautiful ice rink in winter, and concerts year round.must-see-in-chicago-karlaroundtheworld-11
  5. Millennium Park is a part of Grant Park. It is famous for the cloud gate and crown fountain, among other interesting sculptures and
  6. Maggie Daley Park. Every park has cool stuff, of course, but can you really beat the rock climbing wall in Maggie Daley Park? I don’t think so. This has become a huge attraction for locals and visitors alike.
  7. Bike the Marina with a Divvy Bike rental. You can go to Navy Pier and grab some ice cream, or head to the river walk for some fresh air and exercise. Book and rent your bike and have fun with your tour in Chicago.
  8. Ride the Helicopter. Chicago Helicopter Experience is one of the coolest things to do in the entire city! I absolutely loved my amazing experience flying above the skyline. It is the best way to see the city.chicago-helicopter-experience
  9. Logan Square. This area of the city is artsy and YUMMY. I loved the street art and the quaint shops, but what I loved most was the pie from PIE. My drink at Dunlay’s wasn’t half bad, either.
  10. Wicker Park is a historic neighborhood that you can’t miss. It is home to the famous Flat Iron building, which is the site of many art galleries.
  11. Field Museum. The Field Museum of Natural History is a huge museum that you could probably live in. Seriously, you’d never get tired of looking at all the exhibits!
  12. Rookery Building. This beautiful old building is an incredible work of art in architecture and design. You have to see it for yourself to appreciate it.Rookery Building-Chicago
  13. Money Museum. Because who doesn’t want to stare at piles of money? If you can’t see it in your own bank account, may as well look at it here!
  14. Chicago Culture Center. I don’t really know how well this stately building represents true Chicago culture, but it sure is classy! Join the many dignitaries who have set foot in this building and take a look around.
  15. Blue Man Group. Is there really any way to describe these guys? Basically, they’re a bunch of men painted blue who do crazy, funny, and talented stuff. Go see them.

Ways to Save

  1. CityPass Chicago is only $98, and you get a whole lot of stuff for the price. You’ll get admission to Shedd Aquarium, with VIP entry; a fast pass to Skydeck Chicago; VIP entry into the Field Museum; your choice of Museum of Science and Industry or 360 Chicago; and choice of Adler Planetarium or Art Institute of Chicago.


I love CityPass. I’m all about that life. Why do I find it beneficial? For one, I hate lines. The Skydeck line can be terrible, and CityPass one allows you to “skip” the line and get there faster, especially if you are rushing. You get special VIP status in pretty much all the excursion, not to mention saving all that money.

  1. Skydeck is open until 10 PM.
  1. Boat tours are good, they give you history and all, but they’re also $35 bucks. For those who just want to admire and not keen on history and facts, take the Riverwalk— you walk along the river, you see the buildings just the same, you get exercise and you can drink wine, beer or whatever in some of the stops along the way.
  2. If you are keen to learn more about the city, try Free Tours By Foot— there is no set amount, you give what you think they deserve and they give a lot of information.
  3. Big Bus is great for those who don’t like to walk around. It takes you to all the tourist destinations


  1. Deep Dish Pizza is a must for Chicago. We tried it in Pequod Pizza by Lincoln Park.
  2. Try a Bloody Mary; always a good choice.
  3. Public House is awesome.
  4. Dunlay by Logan Square is good; I ate a Cubano sandwich and Bloody Mary
  5. Pot Pan Thai Food has great Panang
  6. Bang Bang Pie in Logan Square has delicious pies.

30 thoughts on “Ultimate Guide to Chicago

  1. I haven’t been to Chicago as an adult and have been dying to go back! I have some old highschool friends who live there that I’ve been hoping to cash in a free stay with! haha This list is great, I really want to do one of the boat tours too! I think it would be really fun to visit during March when they dye the river green for St. Patrick’s day too!

  2. Chicago is one of the cities I want to visit! the Skydeck on John Willis Tower, parksa and the museums are already included on my things to do there list! This is a really useful article to add more to that list of mine;)

  3. Chicago is high on my list of places in the US to go to so i’ll have to book mark this post for when I do go. Great tips! Thanks for including a deep pan pizza suggestion!

  4. I have heard that Chicago is a fine city to visit, there seems to be a ton of fun things to do. That fountain in Millennium Park looks cool. I have yet to make it to Chicago but would love to visit. I agree with using the City Pass we used them in several cities in Europe and they are a great deal

  5. The Skydeck looks both amazing and terrifying (I have a bit of a thing about heights). Is there any limit to how long you can stay up there? I love the idea of being there for sunset and staying to get photos of the city as the lights come on.

  6. Chicago is the last big American city we need to get to!! These tips are great, hope to get there some time next year and take in all that amazing architecture 🙂

  7. I haven’t made it to Chicago yet, but would love to go … I think I would definitely be visiting during the summer though :D! Chicago Boat Architecture Tour sounds like a lot of fun, I had no idea you could do this!

  8. Would love to visit. Though I have never really understood that weird thing in your first pic (and I keep seeing that thing in so many pics) I think CH is lovely, so thanks for the tips.

  9. A week pass for $33 sounds like a very cost effective and efficient way to get around Chicago! I have spent such a limited time in the city, that I haven’t done anything in this post. A boat trip would be wonderful, as would catching the view from the observation deck!

  10. wow Chicago, I’ve heard much about this city but haven’t seen a detailed and fun itinerary like this one yet! The sky tower picture is incredible, looks like something out of a sci-fi film, love it!

  11. Excellent advice! I love Chicago and will incorporate your suggestions on my next visit to the city, The helicopter sounds like an amazing way to experience the city.

  12. I love the pic of the boat on the architecture tour, it reminds me of Amsterdam where it’s super common to view the city from the water. This is always a great way to see a city from a different perspective 🙂

  13. Chicago is an awesome city! Every time we visit the Windy City, we stumble across something different to experience. I think you have covered this city really well in your guide and it’s always nice to have a few insider tips on the best places to eat in a destination. I concur with your comments about the value of the CityPASS. We have used it in NYC, Dallas, Houston and Seattle and were very impressed by the quality of attractions available with serious discounts.

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