One night & driving north
Flying into Chicago (not sure which airport) and spending one night then driving up to door county Wisconsin. What would you do? Stay at an airport hotel and take the L downtown for the night ? Or drag our bags downtown on the L and stay downtown and then L back to then airport for a car?
Trying to have a quick Chicago experience before the main trip but not spend $100 on parking lol
For a one-night stop in Chicago before heading up to Door County, the best choice depends on your priorities: convenience versus experiencing the city. Here’s a breakdown of your options:
If your main goal is a quick taste of Chicago:
- Stay downtown: Dragging your bags on the L is doable if you pack light. Staying downtown lets you experience the Loop, Millennium Park, Navy Pier, and some nightlife without wasting time commuting. You can take the CTA Blue Line (from O’Hare) or the Orange Line (from Midway) directly into the city. This is a good choice if you want a few hours to walk around, grab dinner, or see the skyline.
- Stay near the airport: Airport hotels are convenient and often cheaper than downtown hotels plus parking. This is ideal if you are tired from travel or have an early departure to pick up your rental car and drive north. Some airport hotels offer shuttle service to restaurants nearby, but your Chicago experience will be limited.
Parking considerations:
- Most downtown hotels have expensive parking ($50–$70/night). If you don’t want to pay for downtown parking, staying at an airport hotel and taking the L in is the most cost-effective option.
- You could also park at an airport economy lot ($20–$25/night) if you plan to pick up your car there the next day and still take the train downtown for the evening.
Suggested strategy:
- Fly into O’Hare (Blue Line is fastest downtown). Leave your car in airport economy parking if you already have it or take an Uber to your downtown hotel.
- Spend the evening exploring downtown highlights like Millennium Park, Chicago Riverwalk, or a casual dinner in the Loop or River North.
- Next morning, grab your rental car at O’Hare or Midway and drive to Door County. This avoids the hassle of overnight parking downtown and gives you a smooth start for your drive north.
This approach balances experiencing Chicago quickly while minimizing parking costs and hassle before a longer drive.
