Just recently, I hopped on the cheapest flight I could find to anywhere new. In some ways I really cut my budget (think: that ridiculously cheap flight because I didn’t care where it was taking me), but in other ways it cost me (like, that last minute hotel I booked without searching for cheaper options). But I loved my hotel, so whatever. 

The lowdown

I found Chicago to be relatively affordable. The taxis, public transportation and food seemed cheaper than what I usually spend during a weekend in NYC. It costs to stay in a centrally-located hotel but there are budget options and airbnb if you are willing to stay outside of the central hub. My average meal cost $12.60 and my average taxi ride cost $12.30.

Gimme Some Cash

I had no issue using my Chase Freedom credit card during my visit (racking up some points on it for travel hacking) but also brought a small amount of cash. This came in handy for purchasing a boot of spiced wine at the Christmas Market, but I didn’t use cash for anything else, not even taxis. Every cab I took was equipped with a credit card machine. In case you do need to get some, there are plenty of ATMs located throughout the city.

Here’s What I Spent…

This is everything I spent during my long weekend in Chicago. I could have spent less, and I certainly could have splurged more. As you can see nearly half of my budget went towards the hotel.

Flight: $68

Transportation: $84

Accommodation: $214

Daily Allowance ($36/day): $90

Excursions: $10

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Total: $466

THE FLIGHT

Usually the flight is the most expensive part of my travel budget, but in this case it was my second cheapest category (yay!!). I was able to find low fares to Chicago because it is cold there right now (off season for travel) and I was traveling on Saturday to Monday. If you can afford to take Monday off from work flying Saturday to Monday instead of Friday to Sunday is a great way to find cheaper weekend flights.

For this trip I flew Spirit Airlines, so you know we’re talking budget. Southwest is another great option and usually offers low fares into MDW because it is one of their hubs. Flexibility is key to scoring a cheap flight. If you can’t find one and get stuck shelling out a few hundred for the flight, try to save on your accommodations.

TRANSPORTATION

I spent two and a half days in Chicago and majority of that time was spent walking everywhere. It’s my favorite way to familiarize myself with a new place and it’s seriously useful for saving money. The second best option (with budget in mind) is the L train. You can purchase a ticket for $3 and go anywhere within the city. My train ride from the airport to the city cost me $5.

I took taxis as much as the L train simply because my feet started killing me by Saturday evening. I would typically walk or take the train out somewhere, then get lazy and cab back. It was always easy to find and hail a cab from the side of the road. You’ll notice my most expensive cab ride took me on a quick detour to Pequod’s before catching the L train so I could fly home with some deep dish. Priorities.

L train from Airport to Hotel – $5.00

Taxi back from Christmas Market – $7.05

L train to Lakeview – $3.00

Taxi from Lincoln Park to hotel – $10.25

Taxi from hotel to Pequod’s to L train station – $19.50

L train to Airport – $3.00

Daily parking at BWI ($12/day) – $36.00

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Transportation Total: $84

Together Traveler Tip: You could have cut this part of my budget in half if you catch a ride to the airport instead of paying for parking. BWI also offers a lower rate, $8/day at long term parking.

ACCOMMODATION

The hotel options I looked at were all around the same price range, $90-100/night. Mine was $92/night and came out to $214 with taxes. Ideally I would have spent less, or stayed with a friend, but I figured I could afford the price since my flight was so cheap.

I absolutely loved my hotel, the Freehand, and will be hard pressed to stay anywhere else when I go back. It was centrally located and so convenient for everything I wanted to do. Fortunately they offer dorm rooms on the top floors if you want the same experience on a cheaper budget. Another good option is looking at airbnb rentals outside of the city center. Look for a place near the L train for easy transportation.

DAILY ALLOWANCE

After looking at all of my expenses, I used an average of $36/day in spending money. This covers my meals, snacking and souvenirs – okay you caught me, mostly food. Funny thing was I was sick during this trip so I actually ate fewer meals than I usually would. If I had been feeling better though I would have spent less on breakfasts and put the money towards dinner. This is where you’re budget could easily grow.

Café Integral Breakfast – $12.50

Snack (water and almonds) – $2.18

Giordano’s Stuffed Pizza – $9.79

Spiced wine – $7.00

Southport Grocery + Cafe Brunch – $19.33

French Market Crepe – $5.00

West Town Bakery Breakfast – $12.16

Dylan’s Candy Bar – $13.13

Pequod’s Pizza – $9.21

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Daily Allowance Total: $90

EXCURSIONS

The only tourist site I paid money for was the Chicago 360 room at the John Hancock building. It only cost me $10 (instead of the normal $20) because the visibility was ZERO! I could barely see the streets below, but just had to make sure of this for myself despite the gentleman’s promises. Do yourself a favor and go later in the day after the fog has lifted or check the weather. I also went to the Lincoln Park Zoo and the Christkindlmarket which were both free!

You could easily splurge in this category as well, and I would have if I had more time or had planned my itinerary in advance. $25 for the Art Institute, $40 for the Skydeck VIP pass, $8 for the aquarium, $38 for the architecture boat tour … It will add up.

So how should you budget your trip?

To plan your own trip to Chicago, add up your potential daily cost (decide if you need or want more than my $36/day), the cost of your flight, the average cost per night for accommodations and any transportation or excursions you anticipate. It’s always better to save a little extra for unexpected expenses. Need some help budgeting your trip? Check out my budgeting worksheet here.

I would love to help you plan for your next trip! Shoot me an email or let me know if you have any questions/suggestions regarding budgeting for Chicago in the comments below.

Check out this post if you are looking for hotel recommendations.

And you can even take a look at my suggested itinerary.

Need help planning your own trip? Follow these 5 easy steps for building a travel itinerary.