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Frugal Travels: Short Weekend in Chicago

Updated on August 23, 2016
Enjoying a glass of beer and catching on some work at the Delta Skyclub O’Hare
Enjoying a glass of beer and catching on some work at the Delta Skyclub O’Hare
View from our room at the Sheraton Grand Chicago
View from our room at the Sheraton Grand Chicago
Chicago River View
Chicago River View
Dessert tower at Russian Tea Time
Dessert tower at Russian Tea Time
The Bean at Millennium Park
The Bean at Millennium Park
Little Sheep Mongolian Hot Pot
Little Sheep Mongolian Hot Pot
Chicago Skyline from Lake Shore Trail
Chicago Skyline from Lake Shore Trail

Short weekend in Chicago on the cheap!

Mrs. and I spent this July 4th weekend in Chicago. She flew into O'Hare from nearby Cedar Rapids, IA while I made my way into the Windy City from Charlotte, NC with a short layover at Cincinnati/Northern Kentucky International Airport (CVG). While in transit at CVG and waiting for the Mrs. to arrive at O'Hare, I took advantage of the Delta Skyclubs (earned from the American Express Platinum credit card) at both of these locations to fill my tummy with food and complimentary drinks.

When Mrs. had arrived, we took an Uber to the hotel which we would be spending the weekend in: Sheraton Grand Chicago. My SPG Gold status was recognized at check-in and we were upgraded from a traditional guest room to corner deluxe room with a view of the Chicago River at a higher floor with complimentary lounge access and breakfast for the duration of our stay (note: SPG Gold status does not guarantee room upgrades nor complimentary breakfast, however being a SPG Gold member does provide a host of benefits which I will describe later on). As for the complimentary welcome gift, I chose the 250 SPG points, since the wifi was already included for us.

By the time we settled in in our room, it was approaching 9PM. We decided to go to a late dinner at Bandera which was just a few minutes away. The food was flavorful and delicious (unlike the food we had at the Purple Pig during our last trip). We shared the iron skillet cornbread appetizer, followed by the Mancho salad for the Mrs. while I had the Seattle-style BBQ salmon. Not only were these dishes delicious but of large portions also - we ended up bringing back two boxes of leftovers.

We enjoyed the complimentary breakfast at the Sheraton lounge the next morning before partaking in the Chicago Architecture Foundation river cruise tour. For $44 per person, the tour lasted 1.5 hours and gave us some impressive views of downtown Chicago skyscrapers while sailing down the Chicago River.

It was already noon by the time we disembarked from the boat on Michigan Ave, so naturally we went on a hunt for a lunch spot. We debated on whether we wanted like to return to Russian Tea Time for some good old fashion tea and dessert, but we eventually got lunch at Naf Naf Grill, which is similar to an Middle Eastern Chipotle. After refueling our body, we took a leisure 25 minute walk down Michigan Ave towards the Art Institute of Chicago (AIC). On the way there, we stopped by Millennium Park to see the famous Bean. We then spent the next four hours exploring and admiring the exhibits the Institute has to offer. (This is my 2nd time at the AIC and we had barely explore half of its exhibit by the time we left!). After exiting the AIC, we took a walk down Lake Shore drive, enjoying the scenic and peaceful view of Lake Michigan.

For dinner, we went to Little Sheep Mongolian Hot Pot (LSMHP), which we first encountered in Atlanta. (Since this is a chain, we planned on visiting its location in San Francisco next month as well as in Honolulu sometime early next year!). LSMHP has an all you can eat option for $20/person, which we both did. Unfortunately, the LSMHP in Chicago offered a less variety of veggie options than its Atlanta counterpart.

After we satisfied our stomach, we took an Uber back to the Sheraton and enjoyed a glass of wine from the hotel lounge before calling it a night.

For our 2nd day in the city, we wanted to explore the Shedd Aquarium and the Adler Planetarium, since our Bank of America credit cards offers free admissions to selected museums throughout the country on the first weekend of each month (Museum on Us, a very nice benefit!). We slept in bit late that morning before grabbing fulfilling brunch at Yolk. As it was a beautiful day, we walked down Michigan Ave. and made our way down Lake Shore drive again towards the Aquarium. To our dismay though, we saw a very long line of people queuing to get into the Aquarium. At that moment, we remembered that it was the July 4th weekend (Duh!) and not surprisingly a lot of people were on break. We estimated that it would take hours before we would gain entrance to the Aquarium, so we decided to head straight to the Planetarium. While there was a line at the Planetarium, it was nowhere as long as the one we saw at the Aquarium. After waiting in line for about 20 minutes, we gained entry into the museum. Our goal was to take a look of a fragment of meteorite displayed there. But unfortunately, by the time we got into the Planetarium that exhibit is already closed. We spent about 45 minutes there going through various exhibits before leaving.

The Mrs. and I walked on the Lakeshore Trail, soaking in the impressive Chicago skyline as we made our way towards the Sheraton. Since we had relatively early flights the next morning, we hit the bed early to recharge.

The next morning we took an Uber to O'Hare, and thanks to our TSA Precheck status (fee reimbursed by the American Express Platinum credit card), we were through security in less than 5 minutes.

Overall we had a great weekend in Chicago, and we will be back in October to catch the broadway play, Hamilton. Maybe this time, we will finally try Chicago deep-dish pizza.

CID-ORD (Mrs., AA) - redeemed 7,500 American Airlines miles + $5.60 tax
ORD-CID (Mrs. UA) - redeemed 10,000 United Miles + $5.60 tax
CLT-CVG-ORD (DL) - ~$181, reimbursed by my Barclay Arrival+ credit card
ORD-CLT (AA) - ~$150, reimbursed by my Barclay Arrival+ credit card

Sheraton Grand Chicago - $182.92/night for 3 nights


We put all dining expenses on our Chase Freedom credit card, which offers 5x cashback on rotating quarterly bonuses! The major category for this quarter (July 1st to Sept 30) is dining. This card does not have an annual fee, and right now there is a sign-up offer for earning $150 cashback after $500 spending! Other quarterly categories include gas stations, grocery stores as well as Amazon.


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