How to spend a weekend in Chicago for $100? This actually ended up being not too difficult. I thought it would be much harder, since I’ve always heard of how expensive Chicago is. However, by making just a few changes to the normal travel routine you can save quite a bit of money. I’ve outlined all of my spending over the weekend and have separated it out into categories below! Check it out:
There are many options for cheap accommodation in Chicago. My personal favorite for when I don’t know anyone to stay with is couch surfing. It is free and you get to meet some incredible hosts. Most hosts are excited to help you experience their city and will tell you of cool things to see and do that only locals know about.
If you are uncomfortable with the idea of staying on a random persons couch, the next cheapest option is to take advantage of one of the amazing hostels in downtown Chicago. Depending on the weekend these can be as cheap as $25/night! Hostels are great ways to meet other travelers and experience the city with other backpackers and like minded people!
If there is a large group of you another the cheap option would be airbnb. You can find really nice place right downtown for 150-200/night and if there are 4 or 5 of you that can work out to quite cheap if you don’t mind bringing some sleeping bags.
All of these options make food so much cheaper, since you will most likely have access to a kitchen. You can make some meals at home or prepare lunches in the morning so you don’t have to spend money on eating out. That way you can splurge on that Chicago deep dish pizza!
I stayed with a friend when I was in Chicago who lived about a 30 minute train ride from downtown. In Chicago, staying outside of downtown is definitely a good option as long as you stay near a train station that will take you into downtown. It was super easy to get from the suburb I was staying in to downtown via train. It took about 30 minutes and one ran almost every hour.
My number one recommendation for food is to have one big/fancy meal where you eat out. You can taste the local cuisine or eat at that famous (aka expensive) restaurant as long as you don’t break the bank during your other meals. Whether that means going fast food for lunch and breakfast or buying food at the grocery store and eating it/preparing it before heading out for the day.
One of my favorite things to do when I get to a city is go to the grocery store to pick up some fresh food. You get to act like a local and go grocery shopping while also saving a ton of money by not eating out as often.
Packing lunch for the day lets you eat wherever you want! I like to pick out a nice park and have a picnic out in the grass if its a nice day. You get to people watch, take in some vitamin d, and relax for a little while, while still being able to see the city a bit. Then I have the money to grab a snack at a cute café or go to a farmers market to pick up some fresh fruit. This also makes it so that you tend to eat a bit healthier during the day, which just makes me feel so much better at the end of a long day of sight seeing.
Look up free things to do before you get there! Do your research! Whenever I go to a new city I tend to pick out one museum that I really want to go to (for Chicago that is The Field Museum! I LOVE natural history). Then I look up how much it costs to go there. Most museums I expect to cost around $20, if it costs more than that I immediately right it off as not worth it and console myself with the thought that I will come back one day when I am rich. I also look up which museums are free. Often there are ridiculously cool and quirky museums that are completely free. And the best part of a free museum or attraction is that if you get there and you don’t like it… leave! You didn’t just pay a ridiculous amount of money to get in there, so you won’t feel any guilt if you walk in and leave after 5 minutes.
The Field Museum
Free attractions in Chicago:
  1. The Bean: Now this is a classic and extremely touristy, but every time I go to Chicago I like to go to the bean. I love to get the selfie photo in the mirror and its fun to see all the tourists taking silly photos and just having a good time. What can I say, I like the classics.
  2. Millennium Park: Also where the Bean is. You can also check out Millennium Fountain which has a great view of the city skyline.
  3. Lincoln Park Zoo: Awesome free zoo to wander through
  4. Lincoln Park Conservatory: Check out some cool plants and take beautiful and artsy photos
  5. Swimming at Lake Michigan: If its summer this is a must do! Chicago has plenty of beaches to swim at right downtown. While they may be a bit crowded it is worth it to go float on the water while taking in the view of downtown Chicago.
  6. Navy Pier: Wander through the pier and take in the beautiful view of the city and Lake Michigan

I typically go for convenience when I am only somewhere for the weekend. This is different for every city and every person depending on what attractions you go to, but I typically use Uber or Lyft. I was there with 3 people, so split 3 ways these are generally cheaper. If I was by myself during the day I would use public transport and at night I would use uber or lyft (since I am a solo-female traveler this just typically feels safer for me).
At night I will ALWAYS choose my own personal feeling of safety over cost, and for me that means taking a car service. This may not be every female travelers opinion, but it just brings me more peace of mind.
Now transportation costs is going to differ for every person. For me, it costs a $30 bus ride to get to Chicago, so in total I spend $60 getting to and from Chicago. I don’t have to pay for parking at an airport, since I can walk to the bus station from where I live. This makes it extremely cheap to get there. Also, the bus I take has free wifi! My favorite! So I can do that side hustle while I’m on the bus and make a bit of money, so in my head it is even cheaper!
Typically if I am going somewhere for the weekend (as long as I don’t have to be there a specific weekend) I will try to keep my transportation costs under $150. Flights can be expensive, but if you do enough searching you can typically find a way to get there for cheap. My favorite way to look for flights is to just use googles flight search or skyscanner.
  • Free, since I stayed at a friends house (or use couch surfing if you don’t know anyone)
  • Giordano’s deep dish pizza split between 3 people. $25.00/3 = $12.00 (I’m rounding up)
  • Grocery Store Food: $15.00
  • Coffee from cafe downtown: $4.00
Sight Seeing:
  • $19 – Field Museum ($19 for student pass, $22 for adult pass)
  • Free – Millennium Park
  • Free – The Bean
  • Free – Window Shopping on the Magnificent Mile
  • Free – Lincoln Park Zoo
  • Free – Lincoln Park Conservatory
  • Free – Navy Pier
  • Free – Swimming in Lake Michigan
  • Within Chicago – I bough a weekend pass for the trains which was $8 total and I walked everywhere else
  • Getting to and from Chicago – $60
TOTAL: $110.00
Chicago weekend on a budget
What are some tips you have for cheap weekend travels?

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