Where to stay for NWU football game and Taste of Chicago

Question

Hi,

We're planning a quick train trip the weekend of Sept 5th and would love some input as to where it makes sense to stay (and any specific hotels in Chicago or Evanston)

Plans thusfar:

Friday, Sept 5th

Arrive on 10:40 pm train

Saturday, Sept 6th

Tailgating and game with family and friends of our nephew, a NWU player. (I see now that it is a 7:30 game so I'm not sure how early they'll get started.)

Sunday, Sept 7th

Taste of Chicago (It's our first time so we're not sure how long we'll want or what to expect)

Any other Chicago highlights that we can fit in. (The Bean was fenced off on our last visit so we need a do-over.)

Depart on 5:50 pm train

We're pretty comfortable with public transportation and would like to minimize our walking distances due to knee issues.

Thanks for any advice or suggestions!

Answer

For your weekend plans, it makes sense to prioritize location based on convenience for both the Northwestern University (NWU) football game in Evanston and the Taste of Chicago in Grant Park. Given your preference for minimal walking due to knee issues, staying in downtown Chicago is likely the best compromise. You can use public transportation to reach Evanston for the game without a long drive, and you’ll be right at the center for the Taste of Chicago.

Where to Stay:

Downtown Chicago (Loop or River North): This is ideal for the Taste of Chicago and downtown sightseeing. From downtown, you can take the Metra Union Pacific North Line from Ogilvie or Union Station to Evanston. The trip is roughly 30–40 minutes and drops you near Ryan Field for the game. Staying downtown allows you easy access to public transit, restaurants, and major attractions without requiring much walking.
Evanston: If you want to minimize travel on game day, consider staying in Evanston. This allows you to walk or take a short cab ride to Ryan Field. However, you’ll need to travel back to downtown Chicago for the Taste of Chicago on Sunday, which may add 40–50 minutes on the Metra or a car ride.

Recommended Hotels:

Downtown Options:
- Hyatt Regency Chicago – convenient to Ogilvie Transportation Center for Metra to Evanston.
- Kimpton Gray Hotel – centrally located in the Loop, stylish, short walk to subway and buses.
- Residence Inn or Royal Sonesta in River North – comfortable rooms, easy access to trains/buses, good dining nearby.
Evanston Options:
- Hyatt House Chicago/Evanston – short distance to Ryan Field, full kitchens, spacious rooms.
- Courtyard by Marriott Chicago/Evanston – modern, convenient for game day.
- Local boutique hotels or B&Bs – check proximity to Metra or Ryan Field for easy walking.

Transportation:

Metra Union Pacific North Line is the simplest for downtown ↔ Evanston trips. It’s safe and reliable, with limited walking required at either end.
CTA buses or trains in downtown Chicago will help you navigate to Taste of Chicago and other attractions. Consider short rides or bus stops close to your hotel to minimize walking.
Uber/Lyft can be handy if you want to avoid even short walks in Evanston or from stations to the festival.

Other Chicago Highlights for Limited Walking:

The Bean / Millennium Park: Easy to access from downtown; minimal walking if you park or stay nearby.
Chicago Riverwalk: Scenic and mostly flat, can be enjoyed in short sections.
Architecture Boat Tour: Offers great views without walking, departing from Michigan Avenue/Chicago River area.
Museum Visits: Art Institute of Chicago or Field Museum (if you want indoor activities with limited walking).

Overall, for your plan, staying downtown gives you flexibility and keeps walking minimal while still allowing easy access to Evanston for the game. Use Metra for the game and short CTA trips for Taste of Chicago and nearby sightseeing. This approach balances convenience, comfort, and access to both main events.