It’s no secret that Chicago is one of my favorite cities in the United States. The city is so layered with history, architecture, sports, shopping, art, museums, parks, and food that I never get tired of visiting. So when IHG Rewards Club offered to sponsor me on a trip to Chicago to help promote their #ShareForever promotion, I was like – Duh! Heck yeah I’ll do it! (Besides, the promotion is a great deal – 65,000 bonus points plus a free night to share – just sign up before September 5th)

Chicago offers something new with each visit. One trip I braved the shopping scene on Chicago’s Magnificent Mile. On another trip, indulged in some of Chicago’s great Bucket List experiences. For this trip however, I really wanted to do something a little different. One of my favorite travel shows used to be Rachael Ray’s “$40 a Day” where she would find a day’s worth of amazing things to eat without exceeding her $40 budget.

Since I was flying to Chicago using my frequent flyer miles, and since IHG was putting me up at the Holiday Inn Express Chicago – Magnificent Mile, I decided to see if I could survive in a relatively expensive city (compared to Atlanta) for two and a half days on just $100. (If you’re wondering about the math, I multiplied Rachael’s $40 budget by two and a half.)

Chicago’s Cloud Gate sculpture – also known as “The Bean”

Monday Beginning Balance: $100

I arrived at Chicago Midway International Airport with $100 cash in my pocket. I knew that public transportation would be my cheapest option for getting around town during my stay so I purchased a CTA 3 Day Pass for $20. I followed my Google Maps instructions and took the Orange Line to the Roosevelt Station, then got on the Red Line to the Howard Station where I emerged in the heart of the city. From there, I walked two blocks to the hotel.

By the time I had checked in and put my backpack in my room, I was starved! I hadn’t eaten breakfast before leaving Atlanta. Fortunately Portillo’s was just three blocks away. If you don’t know, Portillo’s is one of those iconic restaurants that is absolutely required if you want to experience authentic Chicago cuisine. Though you can get burgers, hot dogs, salads, fries, and shakes prepared just about any way you like, I opted for their famous Italian Beef sandwich with hot peppers, soaked in gravy, and served on baked french bread. That and a soft drink set me back $11.

As a social media junkie, I ordinarily take pictures of my food before I eat it, but like I said, I was starved and woofed down my sandwich without thinking. So I snapped a few photos around Portillo’s and of someone else’s hotdogs.


Portillo’s is a must for an authentic Chicago dining experience.

After brunch, I decided to walk to the Navy Pier. It was about 1.5 miles which was far enough to alleviate the guilt I had from eating bread for the first time since I starting a low carb diet about three months ago. Here’s a short video made from my smartphone snaps while on the pier.

The hotel was about a mile’s walk back from the pier. It was getting dark and starting to drizzle and I didn’t have an umbrella. To make matters worse, I was hungry again. Not wanting to spring for a taxi, I semi-jogged back to the hotel. By the time I arrived, the drizzle had turned into a steady rain. As I was changing clothes back in my room, I had a brilliant money saving idea for dinner.

Trader Joes!

Yep. A Trader Joes was directly across the street from the hotel! I only got a little wet as I went in. Minutes later I returned to my room with a french baguette, goat cheese brie, some deli meats, and a bottle of pinot noir all for a mere $21. I made a sandwich with 1/2 of the baguette and heated it in the microwave in my hotel room. Since it was still raining outside, I decided to hang out in my room and edit photos in my underwear. After about three hours, I made myself a late night sandwich with the other half of the baguette before turning in for the night. Cash Balance at the end of the day: $48


After a good night’s sleep, I went down and had breakfast in the lobby. It was FREE! There were lots of options but I bypassed the carbs and went straight for the protein – a cheese omelet and some turkey sausage.

The new day brought better weather so I walked about six blocks to the Loop at the Chicago Theater, snapping pictures along the way. My plan was to catch the Blue Line to Wicker Park to visit my niece, Jennifer, who moved there a couple of years ago. After showing me around her ‘hood we stopped for lunch at Dove’s Luncheonette, a Southern and Mexican inspired diner that is one of Jennifer’s favorite places.

Wicker Park

A few scenes from Chicago’s Wicker Park neighborhood (and my fried chicken)

As the wonderful uncle that I am, I picked up the tab, but for purposes of my $40 a day challenge, I’m only counting the $18 I spent for my fried chicken, beer, and tip. As a southerner, I know fried chicken. So I was pleasantly surprised to find some this good in Chicago.

Since it was a pretty day, I decided to walk back to the hotel. It was about a 3.5 mile hike but I really needed to walk off the fried chicken. Besides, walking is always my favorite way to experience a destination. 

My feet were aching by the time I got back to the loop. I knew the Cubs were playing that day and I wanted to go to Wrigley field to soak in the game day atmosphere. I took the Red Line to the Addison Station. I’m pretty sure that I was the only person on the entire train that was not wearing Cubs garb. 

Wrigley Field

Take me out to the ball game!!

I tweeted a picture from Wrigley Field. Seeing that I was in Chicago, one of my local Twitter followers told me that I should really eat at Pizzeria Uno while I was in town. For some reason I couldn’t stop thinking about pizza after that. Though pizza was certain to contain a lot of carbs, I rationalized that it would be wrong to go to Chicago and not eat a Chicago style, deep-dish pizza. So on the Red Line while on the way back to the city, I downloaded the Pizzeria Uno app, and ordered a personal pan pizza online. To my delight, Pizzeria Uno was less than two blocks from my hotel!  Location. Location. Location.

The pizza, tax, and tip cost me about $15. I took it back to my room and washed it down with the rest of the pinot noir I had left over from the previous night. Cash Balance at the end of the day: $15


Since my flight home wasn’t until 2 p.m., I figured I would spend my last half-day in Chicago exploring the city on foot. So after another carb-free (and money-free) breakfast at the Holiday Inn Express, I packed my backpack, checked out of the hotel, and headed out for a little sight seeing.

Here’s another short video I made from my morning’s adventure. It includes the Chicago River; the Crown Fountain, which consists of two 50’ LED structures that spit water; and the Cloud Gate, which is a mirrored bean shaped sculpture that most Chicagoans refer to as simply, “the Bean.”

As time was approaching for me to catch the Orange Line back to Midway, I realized that I hadn’t eaten any lunch. With $15 to spare, I ordered another pizza from Pizzeria Uno. I skipped a drink because I didn’t want to risk breaking my budget. I boarded the train with exactly $0.39 in my pocket. I had done it! I survived Chicago on slightly less that $40 a day – just Like Rachel Ray!

But wait.

When I got off the train at Midway and saw people purchasing train tickets, I suddenly realized that Rachael Ray never paid for transportation on the show – only food and beverages. I actually could have spent another $20. My Cash Balance at the end of this challenge should have been: $20.39.

Using my calculator app, I deducted $20.39 from my original $100, and divided that number by 2.5 days. And TaDa!!! I actually did Chicago on $31.84 a day!!! 

So take that Rachael Ray!

Have you ever tried to experience a world class city on a very limited budget? 

This is a sponsored conversation written by me on behalf of IHG Rewards Club. The opinions and text are all mine.

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