A couple of general questions for a very short stay.

Question

We are looking at flying into Chicago to take the California Zephyr back to California.

We want to do it during the winter time which is supposed to be the best sightseeing time of the year. Most likely the first couple of weeks in February.

We have never been in Chicago and eventually want to take a longer trip there during better weather time. This time we'll probably just stay there 1 or 2 days before the train trip.

Our general questions are :

- Is it best to fly into Midway or O'Hare airport?

- Recommended hotels in a nice and safe zone. Of course not too expensive but nice and comfortable. And preferably closer to the Amtrak Union Station.

- Must see places in the short time we are planning to be there.

Thanks

Answer

It sounds like you’re planning a wonderful short stay in Chicago before your train trip on the California Zephyr! Here are some detailed answers to your questions:

1. Is it best to fly into Midway or O'Hare airport?

Both O'Hare and Midway are major airports in Chicago, but the choice largely depends on your preferences:

O'Hare International Airport (ORD) – O'Hare is the larger and more international airport, offering more flight options. It's about 17 miles northwest of downtown Chicago, and while it is further away than Midway, it’s very well connected to the city through the Blue Line of the "L" train, which takes you directly to downtown in about 40 minutes.
Midway International Airport (MDW) – Midway is smaller, typically less crowded, and located about 10 miles southwest of downtown Chicago. If you're flying with Southwest Airlines, this is your airport. It's connected to downtown by the Orange Line of the "L" train, taking about 25-30 minutes to get downtown. Midway can be more convenient if you want to minimize travel time to the city.

If you’re staying close to downtown and want a quicker, less crowded airport, Midway might be the better option. However, if you want more flight options, especially for international flights, O'Hare might be the way to go.

2. Recommended hotels in a nice and safe zone, preferably closer to Amtrak Union Station:

Chicago is a vibrant city with many neighborhoods to choose from, but since you’ll be close to Amtrak’s Union Station, you’ll want a hotel that’s nearby for convenience. Here are a few good options:

The Palmer House Hilton – Located in the Loop, this historic hotel is only about a 10-minute walk from Union Station. It’s a beautiful, well-known hotel with a great mix of luxury and reasonable rates, especially if booked in advance.
The Kimpton Gray Hotel – A stylish boutique hotel in the Loop, also just a short walk from Union Station. It offers comfortable rooms with modern amenities, and Kimpton hotels are known for being very welcoming and comfortable.
The Residence Inn by Marriott Chicago Downtown/Loop – This hotel offers a great option for longer stays and has more space if you prefer a suite with kitchen facilities. It’s located near Union Station, making it very convenient for your train departure.
The Conrad Chicago – Located in the River North area, just a short cab or "L" ride from Union Station, the Conrad is a more upscale option with excellent service and amenities. It's close to dining, shopping, and attractions like the Magnificent Mile.

These hotels are all in safe, central locations and should be comfortable without being overly expensive, especially if you book early.

3. Must-see places in the short time you are planning to be there:

While you’re in Chicago for just a day or two, there are several key spots that you can’t miss:

Millennium Park & Cloud Gate (The Bean) – Located in the heart of downtown, this is one of the most iconic spots in Chicago. You can take a walk around the park and see the famous Cloud Gate sculpture (aka "The Bean"), which is especially stunning in winter with the snow and the city's skyline in the background.
The Art Institute of Chicago – If you enjoy museums, this one is a must-see. It’s home to thousands of works of art, including pieces by Van Gogh, Monet, and American artists. It’s just a short walk from Millennium Park and is a great way to spend a few hours.
Navy Pier – While Navy Pier is a bit touristy, it’s worth a visit if you’ve got some extra time. You can take a ride on the Ferris wheel, enjoy a hot drink, or simply stroll around and take in the views of Lake Michigan.
The Magnificent Mile – This is Chicago's premier shopping district, but it’s also great for a casual walk. It’s lined with shops, restaurants, and historic buildings, and is a great place to soak in the vibe of the city.
The Chicago Architecture River Cruise – If you have a couple of hours, this tour offers a fantastic way to see the city’s famous architecture while learning about its history. It's especially beautiful in winter, as the buildings are lit up and the city has a quieter vibe.
Skydeck Chicago or 360 Chicago – If you want an unforgettable view of the city, head to one of these observation decks. The Skydeck at Willis Tower (formerly Sears Tower) offers stunning panoramic views, and the 360 Chicago observation deck offers a glass-floored observation area known as "The Tilt" for a truly unique experience.

For winter, I would also recommend taking a walk along the Chicago Riverwalk if the weather is mild. It's a lovely place to enjoy the views, even in February, and you can grab a hot chocolate from one of the kiosks or cafes along the way.

Chicago is a city full of things to see and do, and even in a short visit, you’ll be able to experience some of the best it has to offer. Enjoy your trip, and safe travels on the California Zephyr!

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