In case you missed it, this is a multi-part trip framework. You can catch up on all the segments here:

• Introduction
• New York-Chicago, Staying in Chicago
• Chicago-Seattle, Staying in Seattle, Seattle-New York
• How It Was Accomplished

So, let’s get rolling! The first part of the trip is taking Amtrak from New York’s Pennsylvania Station to Chicago’s Union Station. You’ll be taking the Lake Shore Limited #49 (a favorite of mine for getting to Utica) in a Viewliner Roomette. It’ll take just over 19 hours, but luckily you’ll have a bed for the trip.

This portion of your trip will set you back 19,424 points, which saves you $563.00. You could save ~16,000 points if you opted for the Reserved Coach Seat, but let’s be completely honest, that sounds TERRIBLE. Hard Pass.

One you get to Chicago, you’ll be staying at the Hyatt Place Chicago-Downtown/The Loop from 8/13 to 8/15. It’s a half mile walk from the station to the hotel. You’ll be getting in a little early, so your room won’t be ready for check-in, but hotels are usually pretty good about holding your bag(s) if you want to explore unencumbered.

The two days in Chicago will set you back a whopping 0 points. You may be thinking:  “Sam 12,000 x 2 is certainly not 0.” And you’re not wrong; however, the Hyatt credit card’s sign-up bonus is two free nights at any Hyatt hotel. NICE!

This stopover on your trip gives you ~55 hours to explore Chicago, which isn’t a lot of time, but enough to get a few adventures in:  Millennium Park, a Cubs game (they’re playing the Cardinals at home that weekend!), Art Institute of Chicago, Willis Tower Skydeck, Museum of Science and Industry, and Navy Pier to name a few!

On the afternoon of 8/15, walk back to the train station for your 2:15 train to Seattle!