Chicago 2-Day Itinerary

Chicago, IL

2-Day Itinerary

Adventure without breaking the bank

Believe it or not, Chicago was the trip that got this whole thing started. "Whole thing" as in realizing how possible and easy it is to travel to a new city just for the weekend.

I remember texting my brother on Wednesday before the weekend to see if he had any weekend plans, and low and behold, he was available. So we tapped into our impulsive sides and booked a flight leaving Saturday morning and returning Sunday night so we didn't have to take any days off work or school. We both agreed on the train ride to the plane that we felt content with everything we were able to see in Chicago in such a short amount of time, and didn't even feel rushed. So this was the beginning of it all...

You ready for a weekend in Chicago?

for around $200?

When's the best time to go?

My brother and I went to Chicago in late September, and we couldn't have gone at a better time.

We backpacked the trip because Frontier got us messed up if they think we are paying $110 for a carry on.... anyway, even with the chilly and overcast weather, we didn't need to pack heavy since we arrived right before their 8-month winter began.

Housing

This was my first time staying in a hostel, which I thought was just "hotel" spelt wrong. There are 7 hostels near the city to choose from, but we stayed at HI Chicago.

Having such a great experience in this hostel changed the game for my future in traveling. It was safe, which is the top priority while traveling.

Total cost per night: $48

Transportation

Chicago is amazing for their public transit and walkability rating.

We got bikes in-between our longer bus rides just because we aren't 100% city people, and needed an outlet to explore a little more freely. But if you're solely planning on relying on the public transport and your own two feet, you'll do just fine.

Divvy Bikes will allow you to bike unlimited miles all day for $16.50, and public transport was $2.50 to arrive at each destination.

I'd like to mention that everything in this itinerary is not confined to being chronological, and I hope you take it and make it your own!

Day One

Once you fly into the Chicago O'Hare International Airport, take the Blue Line bus into the city. (Since we backpacked, we wanted to lighten our load and check-in to the hostel early for a locker, costing us $3, which my back will tell you that it was worth it.)

Giordano's

Are you really in Chicago if you don't get deep dish pizza? We were recommended by countless locals to hit up Giordano's, and for good reason- it was fire.

We ordered The Special small deep dish pizza, which could feed a whole family- so don't feel pressured to get a medium or large.

One small deep dish pizza costs us $27.55 pre-tax and pre-tip.

Lincoln Park Zoo

Then, we took a bus over to the Lincoln Park Zoo; a free and outdoor zoo.

This truly was one of the best zoos I have been to, especially with it being free. They had a vast variety of different animals and the area was beautiful and charming to walk around.

Free to enter.

Kayak the Chicago River

Kayaking the Chicago River was both my brother and I's favorite part of our trip. It's the most expensive excursion I've had on Cheap Weekend Travel, but it's for good reason.

We had a private tour and a wonderful guide teaching us unique things about the city for our journey.

Bookings start at $45 for kayaking with Urban Kayaks .

Eat!

Downtown awaits! There are so many great eats along the Chicago River and all throughout the heart of the city.

Oddly enough, for being a big city, it felt incredibly safe and welcoming- kind of like a giant small town. There are great options for mingling and activities throughout the city to meet fellow travelers or locals (which are super friendly)

We ate at Barrio, which was delicious and charming. And got Cold Stone for dessert.

Eating out cost me $25 for the night.

Day Two

Bike Ride

Sunday morning Chicago is best experienced on a bike (Let's pretend this isn't my first and only Sunday in Chicago).

We rode around this route for 7 miles with the Divvy Bikes.

I couldn't recommend doing this more, especially since most shops and museums aren't open early Sunday mornings.

Total cost for Divvy Bikes for the day: $16.50

Chicago Institute of Art

This museum was HUGE! There were so many exhibits and unique pieces.

It provided an opportunity to learn about diverse subjects and cultures. The museum also offered guided tours or audio guides to enhance the experience.

Tickets are $25 for adults and $19 for students.