I’m a sucker for cheap flight deals. Cherish hasn’t traveled much. This combination means when an email pops up that has a cheap flight, a quick shout: “Honey, want to fly to Chicago for $100?” results in a weekend getaway, with a few extra days tacked on. So on August 10, 2023 Cherish made her first trip to the Windy City.
Day 1: Thursday August 10th
The 5:10AM flight out of Atlanta on Frontier Airlines meant we had to wake up at 2:00 AM. From our house to North Springs Marta, to the airport, through baggage check, through security, with a stop for breakfast, and a potty break left us with 30 minutes to spare. It was going to be a long travel day.
We landed at O’HARE at 8:30 AM central time and took a train over to the InterContinental Hotel on the magnificent mile. Check-in wasn’t until after 4:00 so we checked our luggage, grabbed our day packs and went food hunting.
I don’t like to plan much on travel days especially when I know I’m waking up at 2:00AM so it was a light day. Of course a light day when your wife puts on the vacation itinerary “walk a million miles” translated to about 12 miles of walking around site-seeing. We did take a bus to see Wrigley Field (closed) stopping at Smoke Daddy on N Clark Street for lunch. More buses and walking took us to the Lincoln Park Zoo and eventually we found ourselves back to Chicago Pizza and Oven Grinder (also on N Clark Street) for dinner. We crashed hard at the hotel that night.
Day 2: Friday August 11th
From Navy Pier we took a Chicago Architecture River Cruise then ate lunch at Pinched, which is a tiny cafe we stumbled upon walking back toward our hotel. It was another day of walking (around 10 miles) and we took in the shops and sights including the Lego Store and the American Girl store. We ate dinner at Gibsons Italia on N Canal Street and attended the Art on the Mart that evening.
Day 3: Saturday August 12th
The Grand Lux Cafe was a few minutes from our hotel and was recommended for breakfast. We booked a tour for the Willis Tower Sky Deck tour and stopped by The Bean on the way. We had lunch at Portillo’s. Next up was a visit to the Oak Street Beach where we had appetizers at Whispers Cafe on N State Street then we bused back to Eataly where we had a mouth watering Italian dinner. We’ve decided every city needs an Eataly.
Day 4 Sunday August 14th
Our cheap flights meant a red-eye flight back home leaving at 9:55 PM so we had the full day to continue the adventure. On our way to the Chicago Art Institute we found a fast food breakfast at Protein Bar on N Clark Street. After a morning of culture at the art museum we headed back to N Clark Street for lunch at Bub City BBQ than did a bit more walking around until it was time to head back to the airport.
We landed back in Atlanta just after midnight and after a long journey home passed out in our bed happy to be home!