If you follow me on Instagram, you’ll probably be aware that Mr TBG and I are currently on a 3-week trip around America. We’re visiting five cities across the 3 weeks, so instead of my usual weekly spending diaries, I’ll be posting a spending log of what we did and what it cost us after each city. Please note, if you’re looking for a budget travel guide to Chicago, this isn’t it. I’m not saying we guzzled Moet and Chandon every night or anything, but in terms of sourcing budget hostels and low cost eateries, we didn’t do any of that. What this series is, is an honest account of what we spent, on a budget that worked for us. It was important to us that we had enough money saved to not have to think too much about what things cost. We intuitively know that a restaurant with main courses coming in at $60USD can’t be a regular occurrence, but we didn’t want to have to say things like “oh we’d better just have water” or “no don’t order another wine, we’re over budget.” For this reason, we allocated roughly $200USD per day, to cover all food and drinks and any additional activities/purchases that weren’t prepaid for. That $200USD was in total for both of us, and did not include accommodation.

I’m very aware that being able to make such conscious decisions to earn and save enough to have that choice is a huge privilege. To take advantage of such privilege, however, we have worked and saved very hard over the last year, and given up a lot of other things to be able to take this trip. Not everyone will agree with the spending in this diary, but I’m choosing to be open and share our spending and experience with you. if it’s not your thing, that’s cool. Let’s respect our differences and eat a cake made from rainbows and smiles and all eat it and be happy, k?

Anyway, let’s get stuck in.

Where we stayed: The Hoxton, Chicago

What we payed: we scored the opening deal of $75USD per night, plus taxes and fees. Total for 4 nights: $361USD

Prebooked activities: we bought the GoChicago 3-attraction pass for $80USD per person.


We arrived on our Air New Zealand flight around 6.30pm and once we got through the inevitably intense security screenings, we hot footed it to the Uber pick up area without a second thought. After a 19 hour journey, we didn’t want the hassle of getting public transport. We just wanted to get to our hotel and start the holiday as soon as possible (another example of what I meant by our very fluid budget). Our Uber cost us $38USD.

Once we got to the hotel, we dumped our bags, did the mandatory ‘we’re on holiday’ squeal, and headed out to find some food nearby. By this point it was about 9pm, so we ducked into the first place that didn’t have a 3 hour line – The Little Goat Diner – and it was so good. We ordered the messy fun fries, the mac ’n’ cheese and a fried chicken sandwich, which came in at $55USD incl. tax and tip. Then we headed back to our hotel which had a rooftop bar, and had a beer each, which cost $11 all up.

Total for day 1: $104


Our first full day in Chicago saw us up bright and early (thanks jet lag), and bound for Starbucks. We had two cold brews with sweet cream (delish) which cost something like $10. Then, off we went to Navy Pier. Here we got first in line to ride the observation wheel, where two tickets cost us $36. We then went and booked onto an architecture cruise, which was included with our GoChicago pass. It would usually have cost $45 each, so we were already over half way to making the most of the attraction passes. The tour was the Shoreline Sightseeing Architecture tour, and we absolutely loved it. If you’re planning on going, see if you can ask to book onto a tour lead by William. He was our tour guide and he was hilarious, engaging and knowledgable in a completely non-boring way.

Post cruise we’d worked up quite an appetite, so we went off in search of Chicago’s speciality – deep dish pizza. Giordano’s is recommended by just about everyone, so we tried to get a table at the Navy Pier branch, but unsurprisingly it was an hour and a half wait. Instead, we walked to the Michigan Avenue one, and got in straight away. We spent $45 here, incl. tax and tip.

Then we headed off down the Magnificent Mile, and stopped for another caffeine hit at Starbucks, which set us back another $8. Oh, and I found a giant candy store called Dylan’s Candy Bar, and spent $6 here on sweets like the 9 year old I am. While at the Magnificent Mile (Michigan Avenue), we headed into the centre where Macy’s is, and found a cell phone stand called Cellaris. Here you can buy a visitor SIM card with Ultra Mobile so you can make calls and use data in the US. A SIM card each for the duration of our stay cost $88 all up, including tax and setup fees. 

With plenty of the day left to kill, we kept our energy up and walked to Millennium Park as the annual Chicago Jazz Festival was on. We bought 2 huge beers at the event which cost a reasonable $14, and sat down to enjoy some live jazz in the buzzing Chicago atmosphere. With the mid-west sun burning down on us, we also popped into Walgreens and bought sunscreen for $12, as we’d forgotten to bring any with us! 

Stuffed from our deep dish pizza, we weren’t too hungry for dinner, but we’d spotted a cute hole-in-the-wall dessert window at the back of a bar called Bombo Bar that we earmarked for later. We took a walk around the West Loop neighbourhood (towards Goodwill, at my request) to round off the day. At Goodwill I spent $6 on a vintage Bears NFL jumper. Then, we headed back to the Bombo Bar dessert window where we ordered their frozen hot chocolate and a fresh doughnut, which cost $14 all up.

Total for day 2: $237


We started the day with Starbucks once again, which cost $10. Then we headed off to the Art Institute of Chicago, which was also included in our GoChicago pass. Top tip: if you have the GoPass, don’t join the main queue. Head through the front doors and round to the left where there’s a redemptions desk. Here you can convert your Go pass to museum tickets without waiting in the regular line. Entry here would have cost $25 each, so again, we got great value with the Go pass.

Later that day, we cashed in the final attraction on our GoPass, and did the open top bus tour. This would have cost $46 each if we’d paid on the day, so our $80 GoChicago passes certainly paid for themselves. The bus conveniently dropped us at Stop 13, near a diner called Al’s Beef. Mr TBG loved it (and it is world famous), but I’m not the biggest beef fan so I can’t say it was life changing for me. One “big beef” Italian roll, a drink and some fries (we shared so as not to get too full) cost $19. We then stopped by Portillo’s which is opposite, and squeezed in their famous hot dog and a “small” Sprite, bringing the total to a tidy $6. 

Despite being absolutely stuffed from lunch, we really wanted to try Au Cheval, which is renowned as one of Chicago’s best restaurants – and was conveniently right near our hotel. Top tip: Au Cheval is one of the busiest restaurants in town thanks to their world renowned burgers. The only way to get a table is to put your name down early. For context, we put our name down at 4.45pm, and were told there was a 3.5 hour wait. We got in around 7.30pm in the end, and people who walked in around that time were told a further 3 hour wait. They’re pretty efficient once you’re in there – and the burger was very good. We had a burger each, fries to share, and 3 beers between us, and spent $65 including tax and tip. Then we made for our hotel rooftop again, and slammed down $50 worth of drinks thanks to Mr TBG’s love of a tequila sour. My 2 beers only cost $10 – just saying. 

Total for day 3: $151


Our last full day in Chicago started off with grand plans of setting out early for a long walk along the Lake Michigan shoreline, but instead, we got distracted by the incredible atmosphere on the Hoxton rooftop. The rooftop pool and cabana beds (which hotel guests get first dibs on before 11am, might I add) were just too inviting. So we sat down for a coffee and planned to head off in an hour. 3 hours and two cocktails later, we still hadn’t set off by noon – though that is what holidays are for, I suppose. The cocktails cost us $35, and the coffees $10. Once we’d played a fun game of choosing which poolsider to give our sought-after cabana bed to, off we went on our much delayed walk. En route, we stopped at Pastoral Bakery to get some lunch and take it to Millennium Park. Here we got a sandwich, a cheese plate and some olives, and spent $28. Note here: we had read on a few blogs that you could get pre-packed picnics, but the staff didn’t seem to want to make one, saying they were ‘catering orders only’. We sensed it was an element of ‘working on labour day’ disgruntled-ness, so we went along with it and built our own instead. That said, it did make it about $20 cheaper, so there’s a TBG tip for ya.

A stop at Walgreens for some iced tea, crisps and miniature wine (for $1.59, might I add!) cost us $11, followed by a $2 donation to a homeless guy with a cat outside.

After lunch we set off on our long walk, and on a hot day, I couldn’t resist a $3.50 snowcone. We walked from Millennium Park, round to Buckingham Fountain, along the shore to the planetarium, and then all the way back the other way to Navy Pier. There is a seasonal free ‘tram’ that they call a ‘trolley’ that you can pick up around the city between Navy Pier and Downtown, too. As it was so hot on the walk, I was gasping for a Starbucks peach iced tea when we got there, so we spent $13 on two venti sized drinks. No regrets. 

Since it was close to sunset, we wanted to check out the 360 degree views from the North Michigan Av observation deck. Top tip here: don’t pay for the observation deck. Head up to the casual Signature Lounge instead, where you can see the views for just the cost of your drinks. We spent $22.50 here. I controversially didn’t tip as one of the male staff had yelled at me for not understanding where to wait to be seated. I cried because I’m dramatic like that, but given his aggressive nature towards me, I dared not to tip. Sorry, America.

We were exhausted from an almost 20,000 step day in the heat, so we surrendered to a $9 Uber back to the hotel. As it was Labor Day, a lot of restaurants had closed early, but we found a cute little Mexican in the West Loop area called La Josie, where we had delicious tacos, chips ’n’ dip, this amazing corn cheese side dish and a Mexican mac ’n’ queso. This, including tax and tip, cost $58. Then, we spent a final $9 at Bombo Bar on the way back to the hotel on one last frozen hot chocolate! 

Total for day 4: $182


We woke up to our 5am alarms to head to Washington DC to find that our 8.45am flight had been cancelled. Luckily, SouthWest Airlines had automatically booked us onto a 12.05pm flight, so we had a couple of extra hours to enjoy the Hoxton. We had coffee in the bar, and ambled to Chicago Midway airport on the train, which saved us the Uber we’d planned to get at 5.30am! We had drip coffee so it was just $5.50 for both, and the train tickets were $3 per fare, totalling $6. A quick Dunkin Donut stop at the airport for a plane snack set us back $1.40, and we quickly shared a panini and a water for $14 before boarding.

Total for this mini day 5: $26.90

Tah-dah! That’s a wrap. Total spending for our almost-4-day stint in Chicago with no desire spared: $700.90.

Our next spending diary will be…Washington DC! Stay tuned.