4 days in Chicago for $22.40

The Art Institute of Chicago is the home of this bad boy An American Gothic. I’m not an art aficionado, but I'm pretty sure this was something Mr. & Mrs. Douglas did on Hee Haw.

What do you do when you realize you haven’t set foot in Chicago in 25 years? You whip out your calendar and make a plan. You can fly there and stay in a nice hotel for almost nothing! Here’s what we did.

If you have questions about how you can do it, email me!

Flights are expensive. Thankfully we have a Southwest Companion Pass. In short, anytime you book any flight with money or Southwest Rapid Rewards points, your companion flies free! Your companion could fly for free DAILY if you wanted. Read my post about the Companion Pass here.

We booked the non-stop flight from Los Angeles to Chicago Midway using bonus points earned from Southwest’s credit card promotion. Bottom line: we both flew for free, saving about $1,000. All we had to pay was the TSA Security fee of $5.60 each way. Not too shabby.

I also found a booklet of free Southwest drink coupons – from 2007!! Yes, 12 years old. It was a very good year. I noticed the expiration date after we ordered. Oops! The flight attendant said she’d get us a couple rounds in exchange for the booklet – to take it out of circulation. Deal! The lesson here is to make sure you are a frequent drinking flyer or your tickets will expire.

Chicago’s famed “L” train took us from the Chicago Midway airport to two blocks from our hotel in downtown Chicago’s Loop for $3 a pop. This was during Friday rush hour. It could not have been simpler. I was especially fond of the bike curb on the side of the stairway.

Hotels are expensive, too. I had two free night awards sitting in my account. My Marriott credit card gave me a free night every year. I chose the Aloft Chicago Downtown River North on Clark Street. I booked the third night with Marriott bonus points that I’d earned from meeting the Marriott credit card spending requirement. This saved me another $1,000 for the room alone.

Important to note: when you use free nights or points instead of cash, you avoid getting charged hotel tax. Chicago’s hotel tax is 17.4%. Using points and free nights instead of cash saved us another $174.

I liked that it had a bar and restaurant on site.

If you are keeping track… it cost each person $5.60 to fly there and $3.00 on the train to get to the free hotel. Instead of being in Los Angeles, we were in Chicago – ready to go do stuff!

By saving over $2,000 on travel and accommodations, one can splurge a bit. We dropped our bags at the Aloft Hotel and then hit the Tiny Tapp bar on the Chicago Riverwalk where Friday Happy Hour was in full swing on a sunny afternoon. See it behind my big jughead.

Then to a restaurant called Maple & Ash where all the beautiful people were. Ever see Sofia Vergara or John Stamos in person? It was that kind of freakish beauty.

Turns out being nice is a money tip. While standing at the bar, seats opened up in front of us. We’d been sitting all day so we waved in folks we’d come to know as Rita and Dean. To show their appreciation for the seats, they bought our drinks! We thanked them, careful not to stare too long at them for fear of falling under their pretty spell.

Then we hit Second City’s late show to see the stars of tomorrow today.

Day Two was the 36th Annual Chicago Blues Festival in Millennium Park downtown. It was free to the public. I was too busy getting my blues on to snap any great pics. Here’s Latimore playing a couple songs during his afternoon sound check.

We’re baseball fans who needed to see the spruced-up Friendly Confines of Wrigley Field. It was the Cards vs. Cubs. Whenever St. Louis comes to town, it’s a sellout. Full disclosure, I had a guy. A ticket connection. So, we lucked out with some sweet seats. But even if you don’t have a guy, here’s the next best thing.

Avid reader Jeff C. gave me the heads up about the Cubs’ 10/Sixty Tickets. For every home game, the Cubs have a drawing for 60 lower-level seats for $10 each out the door.

Sunday, we brunched with my old friend Joe and then swung by the Blues Festival again on the way to The Art Institute of Chicago.

Our final night was spent listening to an Irish Music jam at Galway Arms. Check it out. Paddy Homan organizes and performs at The Galway Arms Sunday Session every week. The musicians set up in a corner of the bar and let ‘r rip! Pretty cool!



On Monday morning, we took the $3 train back to Midway and jumped on a $5.60 flight back to 100-degree LA.

If you want some of this free air travel and hotel action, it’s pretty easy to do. You can find more info under “Chip’s Favorite Credit Card Offers” at the top right side of this website.  Then click the “Airline Credit Cards” or “Hotel Rewards Credit Cards” links for more info. Email me if you have any questions.  Full disclosure: I may get a commission if you use my links, so… Thanks!



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