If you haven’t been to Chicago, maybe it is time you planned that family vacation. Chicago is an incredible city (as long as you don’t go there in the winter). You’re probably asking yourself – how much does a trip to Chicago cost? The majority of people spend a little under $200 per day on a trip to Chicago. Usually, 20% on meals and another 20% on transportation. Sure, it isn’t cheap, but it doesn’t have to blow your budget either. Our goal today is to answer the question: What is the cheapest way to plan a trip to Chicago?…but not just the cheapest, the cheapest that you will really enjoy. Let us get to it.
When to Visit Chicago to Get the Best Prices
When you’re planning to visit Chicago, you may think to go there in winter. Don’t do this. Sure, things are cheaper, but you won’t be able to really enjoy the city. Chicago has been ranked the 6th coldest major city in the USA. Instead of winter, visit during the Fall (Sept & Oct). The weather will be warm and comfortable. On top of this, there are tons of festivals where you can enjoy Chicago’s cheap eats and have fun on a budget.
You can also go in the Spring. Usually, you can find the cheapest flights to Chicago in the month of April and the weather, while not warm, will be bearable (almost 60).
Where to Stay in Chicago
So…you have plenty of options here. There are hotels, apart-hotels, and Airbnbs. Each has its own benefit.
If you are going on your Chicago vacation with family, you may want to look at hotels, particularly kid-friendly hotels. Why? Many of these hotels will have amenities like indoor pools, video game rooms, and kids eat free deals for breakfast.
Apart-hotels are also great because they usually have kitchens that allow you to cook.
However, my favorite places to stay are Airbnbs. Why? When you stay at an Airbnb, you have more than just one room (giving you more privacy), they sometimes have washers and dryers, AND you can decide to look for a location with a kitchen. Why is this important? You can make breakfast at home (usually the most overpriced meal of the day), pack some snacks, and when you’re done you can come back and relax as if you were at home.
Cheap Eating in Chicago
Sure, you can spend a bundle in Chicago if you want to. Heck, one of my fave restaurant Naha is in Chicago and it ain’t cheap…but worth every penny. That being said, you can be smart about where to splurge and where to save. Chicago is a city known for its delicious cheap eats. There’s deep-dish pizza, Chicago-style hot dogs, and lesser-known – but equally delicious and affordable Polish restaurants (Chicago has some of the best Polish food in the US).
You will want to check out:
- Rich’s deli
- Farmer’s Pride
- Portillo’s
- and Birchwood Cafe
Here are a few other ways to save on eating out in Chicago:
- do your research to find the best Chicago restaurant coupons.
- If you are crazy enough to go in the winter, check out Chicago restaurant week.
How to Find Cheap Things to do in Chicago
Here’s a breakdown on how to get cheaper admissions to things to do in Chicago:
- Check out the Chicago CityPASS. With it you can save up to 50% on some of Chicago’s top attractions including the Shedd Aquarium, Skydeck Chicago, and the Adler Planetarium.
- Research Chicago’s Free Museum days
- Bring your (or your kid’s student IDs. Many places offer student discounts).
- Take a free walking tour. Just make sure to have enough to tip your guide at the end.
Free Things to do in Chicago
- Take a stroll on the Chicago Riverwalk
- Check out the Smart museum of art
- Get to know the National Museum of Mexican Art
- Go to the Chicago Lakefront Trail
- and spend a day at the Zoo
Cheap Chicago Transportation
If you love to walk, you’re in luck. Chicago (just like New York) is an incredible walking city (as long as it’s not winter). The city is grid-based, so it is hard to get lost.
Chicago also has great public transportation. The CTA (Chicago Transit Authority) is the 2nd largest public transportation system in the USA. The metro is connected to the airport so you don’t even have to take a taxi to get into town.
Chicago is also a bike-friendly city, so rent a bike and have a great adventure. There’s even a great bike share program called Divvy.
We wish you a wonderful (and cheap) Chicago vacation. Don’t forget to check back and tell us how it went!