I went to Chicago for a weekend in September and did not do one touristy thing. No boat tour, no Bean selfie, no tickets to anything. I walked, I ate, I caught up with people I hadn’t seen in a while, and one night out I had more to drink than I needed to.
So when I sat down to work out what a weekend in Chicago cost me, I figured the answer would be small.
It was $682 BEFORE THE PLANE LEFT THE GROUND.
In short: Two nights in Chicago, Friday to Sunday at the end of September 2026, just me: one adult, one room, nothing split. I paid about $1,216, and $682 of that was the round trip flight. Everything with a price on it came to $1,672.06, and $456.12 of it was covered, so it was never my money. The table below shows exactly which lines.
The short answers, before we get into it
How much does a weekend in Chicago cost?
About $1,216 for me, for two nights solo in September 2026, and the $682 round trip flight was more than half of it. My one paid hotel night was $331.71, including $52.71 of taxes and fees. Food, one drink and a tea came to about $123. Things to do came to $0.
Trip taken in September 2026. These are the prices I paid, not estimates or averages. The tea is the one number I’m rounding.
What a weekend in Chicago cost me, all in: about $1,216
Let’s gather the coins real quick.
| What | I paid |
|---|---|
| Round trip flight | $682.00 |
| Hotel, night one, citizenM: $279.00 room plus $52.71 in taxes and fees | $331.71 |
| Hotel, night two | $0.00, covered |
| Uber to my home airport | $56.65 |
| Uber from O’Hare, an $82.93 fare with $60 off | $22.93 |
| Uber back to O’Hare, a $52.49 fare | $0.00, covered |
| Food on Friday, at the airport lounge | $0.00, a card perk |
| Breakfast on Saturday | $24.09 |
| Lunch on Saturday, Sushi San | $47.56 |
| Food at a social thing I never ate | $25.00 |
| One drink on Saturday night | $20.00 |
| Every other drink that night | $0.00, covered |
| Tea | about $6.00 |
| Breakfast and lunch on Sunday | $0.00, covered |
| Things to do | $0.00 |
| Total | about $1,216 |
Everything that had a price on it came to $1,672.06. $456.12 of that was covered: the second hotel night at $343.63, $60 off one ride, and all $52.49 of the other. That’s 27 percent of the weekend, and it’s the reason my number is smaller than yours would be.
So if you’re pricing the same weekend with nothing covered, start at $1,672.06 and go up from there, because Friday’s lounge food, Sunday’s two meals and the rest of Saturday’s drinks never had a price on them, and they aren’t in either number.
The flight cost more than both hotel nights
$682 round trip. Both hotel nights together, at full price, were $675.34.
Hmm, let’s run that back, because it caught me off guard. All weekend I thought of this as a cheap trip. Half the hotel was covered, I didn’t buy a ticket to a single thing, and Friday’s food was free at the lounge. The flight was still FIFTY-SIX PERCENT of what I paid.
Everything else I spent, the hotel night, the rides, the food, the drink and the tea, added up to $533.94. The plane ticket beat all of it put together by almost $150.
Which is why, for a Chicago weekend, you price the flight first. The hotel is where everybody goes looking for savings, and on this trip the hotel was the smaller problem.
The cost nobody warns you about: getting to your own airport
$56.65. That was the Uber from my place to my home airport, and it was the priciest ride of the whole weekend by a mile.
Both Chicago rides together cost me $22.93. The one from O’Hare was an $82.93 fare with $60 off, and the one back was covered whole. So the cheap end of this trip was the big city and the expensive end was my own neighborhood, which I did not expect to be typing.
I already wrote a whole post about four Uber rides that cost me $283 in New York. I apparently learned nothing from it.
What I would skip: $25 of food I never touched
There was a social thing on Saturday. I paid $25 for food there, got caught up talking to people, and never ate a bite of it.
Yeah, girl, no.
And the next morning breakfast and lunch were covered and better than I expected, which made that $25 sting a little more. If you’re not sure you’ll eat it, don’t prepay for it. Buy food when you’re hungry, sis, not ahead of time because somebody offered.
The best part cost nothing
Better yet, let me do you one better.
The river walk. I went on a sunny afternoon, watched a tour boat go past full of people who had paid to be on it, and spent zero dollars. Chicago is a very good city for doing nothing on purpose.
And the people. Catching up with folks I hadn’t seen in a while, plus a few new ones, was the whole point of the weekend for me. None of it shows up in the table and it’s most of what I remember.
The honest part
It was productive and it was fun, and for me those two don’t usually turn up in the same weekend.
It was also a lot. Getting ready for it took more work than I thought it would, and by Sunday I was tired in that full-body way where even your hair feels tired. Some of that was the prep. Some of it was the night I went out with people and had more to drink than I needed to, and the next morning I was hungover with nobody to blame but me.
The title is mostly a joke. Some of the weekend was the kind of group stuff I usually go into ready to roll my eyes at, and I came out of it wanting to learn more, which I did not see coming. Not bad at all.
If you’re planning a weekend in Chicago
- Price the flight before the hotel. On my weekend it cost more than both nights together.
- Sort the ride to your own airport before you leave. Mine cost more than both Chicago rides combined.
- Walk the river walk. It’s free, and it’s the part I’d send you to first.
- Don’t prepay for food you might not eat. $25 of mine went in the trash.
- Eat at the lounge on travel day if a card you already carry gets you in. Mine covered Friday’s food. Whether a lounge card is worth paying for is its own question, and I did the math on a $695 one here.
About $1,216 for two nights, and more than half of it happened in the air. One $25 plate I never touched, one hangover I earned, and a river walk that didn’t cost a thing.
RELATED POST: Four girls trips, side by side, with the all-in cost of each · The other Chicago trip: four of us, four days and a $546 hotel bill · What four days in New York ran me, about $2,160
Grab the free money checklist before you book your next weekend away. And price the flight first.
#bigsisenergy