Braves Baseball in Chicago — Wrigley Field, Lake Michigan & A Weekend With Friends
Delta Flights Into Chicago — Three Travelers, Three Strategies
To minimize flight expenses, we combined different strategies for the three travelers:
- Me: Paid a $375 cash fare.
- Patrick: Used a Delta Companion Certificate on the same reservation.
- Brendan: Used 25,000 SkyMiles.
We flew into Midway for the best outbound fare and home from O’Hare for the best return options. Upon landing, all three families headed straight to the hotel before immediately exploring Chicago on foot.
Hyatt Regency Chicago — Centrally Located & Perfect for Families
We stayed at the Hyatt Regency Chicago, which was walking distance to Millennium Park, the Riverwalk, and Lake Michigan—a huge advantage given how much we walked. For our three-night stay, we used 18,000 Hyatt points per night, significantly saving on the retail rate of $421 per night.
We skipped the Club Lounge and ate breakfast locally each morning. Our two favorite spots were Wildberry Café and Pittsfield Café. Each night, all three families met in the hotel bar before dinner—adults grabbed a cocktail and the kids got snacks—making it our nightly reset.
Friday — Wrigley Field Tour, Braves vs Cubs & AJ Minter
Friday was centered on baseball. We took the train to Wrigley Field for a stadium tour focused on the ballpark’s history and unique charm.
A major trip highlight occurred before the game when AJ Minter walked by and stopped to sign every one of the kids’ jerseys. Meeting an Atlanta Brave outside Wrigley Field was a huge moment they are still talking about. Despite the Braves losing the game, the energy in Wrigley and the earlier Minter moment made the day a win. Dinner that night was excellent seafood at Shaw’s Crab House.
True Cost Breakdown
Our strategic use of points and perks resulted in significant savings:
| Category | Retail Cash Price | What We Paid | Value / Savings |
|---|---|---|---|
| Flights (3 tickets) | ~$1,650 total | $375 cash + 25K miles + Companion Cert | ~$900 saved |
| Hotel (3 nights @ $421) | ~$1,263 | 54,000 Hyatt points | ~$1,263 saved |
| Total Trip Value | ~$2,913 | $375 + 25K miles + Companion Cert | ~$2,163 saved |
(Estimates based on fares and rates at time of travel.)
Why This Trip Worked So Well
Chicago cemented itself as one of our favorite baseball destinations. It was incredibly walkable, the L train made getting to Wrigley simple, and traveling with close friends ensured easy rhythms. Every kid got a major highlight moment, and the adults had a great time too. We would happily repeat this trip.
➜ Next in the Series: Stadium Trip #4 — San Diego: Pacific Views & Petco Park
A Chicago weekend with friends anchored by Braves baseball at Wrigley Field was fun, easygoing, and saved nearly $2,200 using points and perks.
