Ultimate Chicago Guide: Your Epic 5 Day Itinerary

Oh Chicago, Illinois. Home to a collection of unique architectural designs and the famous Chicago Cubs, this city is a midwest dream built along one of the worlds largest freshwater sources, Lake Michigan.

Whether you’re making a quick stop on a lengthy North American tour, or you’re looking for a short getaway – Chicago is the perfect place to call home for a few days.

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Ultimate Chicago Guide: Your Epic 5 Day Itinerary

  • Best times to visit: Summer + Autumn
  • Currency: USD
  • Personal Safety Rating: I felt relatively safe during the day as long as I didn’t go south of the Loop. At night, I’d recommend taking an Uber to your destinations or if you’re with a friend, it’s okay to take the L-Trian.

 Ultimate Chicago Guide - Your Epic 5 Day Itinerary

Getting There

By Plane:

If you’re coming from outside North America, you haven’t much choice in how you’ll get to Chicago. Even if you’re from somewhere nearby, it’s often much easier to just hop on a plane rather than drive there. Below, I’ve listed a few of my favourite websites to help score me cheap flights:

  • Momondo
  • SkyScanner
  • Google Flights
  • Scotts Cheap Flights
  • Hopper

By Train:

If you’re coming from within North America, taking the train is always an excellent way to see the countryside. Although, I wouldn’t necessarily recommend taking the train from somewhere like Arizona to Chicago – that could take forever.

I’ve never personally taken the train to Chicago, but one of the recommended websites I came across for booking train tickets was Amtrak. If you have any better suggestions please let me know in the comments below!

By car:

Road trips are always a good idea, right?

If you don’t already own a car, it’s super simple to rent one from Enterprise for your trip. Don’t forget to factor in the cost of gas, snacks, meals etc!


Depending on what time of year you’re visiting, accommodation in Chicago can be expensive. I’ve stayed in both hotels and AirBnB‘s in Chicago, and the most budget-friendly way to safely stay in the city is through booking an AirBnB (unless you snag an incredible hotel + flight deal somewhere).

If you’re interested get $45 CAD off your first booking here!

Sample Guide

Before we get started, I just wanted to note one thing!

One of the best things I did on my first trip to Chicago, was buy the Chicago CityPass. With this pass, you’ll have priority access to up to 5 Chicago Attractions for $106 USD which comes to 53% off the attractions if you were to buy them separately. The pass includes access to:

  1. Shedd Aquarium
  2. Skydeck Chicago
  3. The Field Museum
  4. Museum of Science and Industry OR 360 CHICAGO Observation Deck
  5. Adler Planetarium OR Art Institute of Chicago

It’s also valid for 9 consecutive days so you don’t have to complete each attraction on the same day!

Day 1


Millenium Park

Located in the Loop and home to the Giant Bean, Millenium Park is a must do if you’re heading to Chicago for the first time (or a second, or a third). I’d recommend taking a stroll around the park as there’s always something going on and the amphitheater is something else. Plus, it wouldn’t be a trip to Chicago without taking a few selfies with the famous, reflective, Giant Bean too!

Best part – it’s completely free!

Art Institute of Chicago

Have you ever watched the movie Ferris Bueler’s Day Off? Because if you haven’t make sure to watch the 1980s classic before embarking on your ChiTown journey. Of the many iconic Chicago scenes from the movie, the Art Institute of Chicago is one of the best (in my opinion). You’ll see hundreds of art pieces from famous artists like Andy Warhol and Picasso. It’s easy to spend an entire morning or afternoon here, it’s that good!

Cost: Included in your Citypass!

Rooftop Bar-Hop

Yay you made it to Chicago! Now it’s time to celebrate!! Even if you’re not a drinker, the following rooftop bars are excellent ways of viewing the skyline from all over (and they don’t have cover!). My favourites are:

  • Ace Hotel (view pictured above)
  • The Up Room (an intimate 13th-floor lounge atop the art deco Robey hotel)

Cost: Drinks average about $6 USD and up.

Places to Eat:

  • Wildberry Pancakes & Cafe: this place is always packed but totally worth the wait. If you’re with a friend, I’d recommend sharing one meal because the portions are giant!

Day 2


Shedd Aquarium & Field Museum

If you have a rainy day on your hands – I’d highly recommend checking out both the aquarium and natural history museum. They are right next to each other and super easy to get to by the L-Train. Plus, both attractions are on the CityPass and will take up the majority of a day.

Don’t forget to take a look at the Chicago Skyline from this location! I swear Chicago is filled with #viewsfordays.

Cost: Included in the CityPass!

Places to Eat:

Day 3


Magnificent Mile

Walk along the famous shopping district of Chicago and take in the sights of the unique buildings surrounding you. Two years ago, they even had a Cards Against Humanity Museum (lol!). This is also a great place to grab those souvenirs *cough* Cubs hat *cough* before your trip ends!

Cost: However much you spend at the shops!

360 Chicago Observation Deck

Pictured above is the view of the North side of Chicago from the 360 Skydeck. If you look close enough you can even see Wrigley Field in the distance (not really, but it’s out there!).

Cost: Included in CityPass

Belmont Harbour

Before you make your way to Wrigleyville (ah!), I’d highly suggest walking along Belmont Harbour. It’s a bit of an off the beaten track location with another incredible view of the entire city from a distance. Like I said, #viewsfordays. There’s also a bird sanctuary and various other outdoor activities in this area.

And speaking of Wrigleyville…

Cost: FREE

Wrigley Field

If there’s anything you MUST do while you’re in Chicago, it’s to see a Cubs game at the infamous Wrigley Field. Even if you’re not a baseball fan, there’s something about the classic American baseball field that really gets you wired up for the ball game (and may make you a fan for life…).

Cost: Tickets are more expensive (especially with the recent Cubs World Series Win) so if you aren’t that interested in going to a baseball game, it’s worth it just to explore the area. It’s super high energy and there are plenty of places to eat and drink.

Places to Eat:

  • Cubby Bear

Day 4


Navy Pier & Architecture Tour

Today, explore Chicago’s most popular pier and book yourself on one of Chicago’s most talked about tours – the Architecture Boat Tour. There are a few different company’s you can go with, but of course, I went with the one that stood out most: the yellow Seadog boat (and it did not disappoint!). My friend and I had an amazing experience with Seadog Cruises on the River and Lake Cruise. This cruise includes a tour of the buildings along the Chicago River and a jet cruise in Lake Michigan with… you guessed it… another view of the skyline!

Cost: $41.95 USD online.

Places to Eat:

  • Giordano’s on Navy Pier for Deep Dish Pizza
  • Garret Popcorn for Chicago Style Caramel and Cheese Popcorn

Day 5


Willis Tower

Beat the crowds and head south to the famous Willis (or Sears) tower in the morning of your last day in Chicago. Once the tallest building in the world, Willis Tower’s Skydeck enables you to see the city not only through the floor to ceiling windows, but through a clear glass ledge, too!

Cost: included in your CityPass!

Chicago Riverwalk & Kayak

Now I don’t know about you, but when I first saw people kayaking in the river, I immediately wanted to do it myself. But I definitely didn’t want to kayak in the middle of all the cruise and tour boasts. No, no, I wanted the off the beaten path experience (duh) so my friend and I decided to find a kayaking spot closer to Goose Island. To do this we chose Wateriders Kayak Tours located at 500 N Kingsbury St. I highly recommend kayaking around Goose Island as you’ll experience less boat traffic with a relaxed feel.

Cost: $25 USD (for a 1 hour kayak rental)

Conclusion + Itinerary & Budget Template!

And there you have it! Your Chicago Guide! The best thing about this itinerary is that you can easily cram everything into 3-4 days if 5 days is a bit too long!

I’d also love to hear about your experiences in Chicago. What activities would you add to this list? What would you take out? I’d love to hear your thoughts in the comments below!

Buuuuut I know you’re SUPER eager for your free Itinerary & Budget Template so here it is & I hope you enjoy!

Thinking about planning a kick-ass solo adventure? Get your FREE Itinerary & Budget Template Here!


Ultimate Chicago Guide - Your Epic 5 Day Itinerary  Ultimate Chicago Guide - Your Epic 5 Day Itinerary Ultimate Chicago Guide - Your Epic 5 Day Itinerary