Chicago: food tour in 24 hours

I was in Chicago a few weeks ago on vacation and stayed in River North. I'd suggest the DoubleTree since it's closer to the Magnificent Mile. I did a food walking tour and among the stops we ate at Portillo's (really liked it) and Al's #1 (it was ok).

I'm guessing when you say arrive at 4pm and leave at 5pm the following day those are flight times. So a 24-hour pass might be useful for public transit since it starts when you activate it, not by calendar days. You can use it on your trip to get to/from the airport as well as on buses around town. I installed the Ventra app on my phone and loaded a pass onto the app. I think they also sell 1-Day paper tickets. Google Maps was great for figuring out how to get around by public transit.

You may find that strolling the river promenade isn't enough to keep you occupied. If you're there on a day they're open then the Art Museum may be of interest or something like the Field Museum, both easily reached by bus (the Art Museum is even in walking distance). Or you might want to do one of the architecture walking tours offered by the Chicago Architecture Center. In the evening Winter's Jazz Club is right in the River North area.

I lived in the 'burbs as a child. My parents did not allow us to eat hot dogs (due to cost), so I have been eating them ever since.

Portillo's is a hoot. It's not the only hot dog place in Chicago. Many recommend SuperDawg. Other Loop restaurants: Berghoff for German, Topalabampa for high-end Mexican - Rick Bayless - can be expensive.

Thank you for the replies so far.

I will see if SuperDawg is easy to reach. I watched a YouTube video about it.

Where can I view the Chicago skyline?

Is Chicago safe, not sure about that?

Either of those Hiltons will be fine for safety. I live very near the Home2Suites. H2S likely will be a bit quieter than Doubletree as not in the more touristy zone. And it is on the same street as Portillos (Clark St at Ontario St). But Portillos is walkable from the Doubletree too. I don't have a recommendation for Puerto Rican smashed plantain sandwiches. But street style Mexican food is available at the "annex" to Rick Bayless main restaurant Xoco. xocochicago.com. Xoco is also on Clark St closer to the river. And if you wanted a little sightseeing, also close to both hotels is the Museum of Contemporary Art. In summer they have some outdoor evening events. https://mcachicago.org/ Or the Driehaus museum. One of the last of Chicago's old mansions in River North, furnished for that time period. They have very good rotating exhibits on the upper floors and a nice little gift shop up there too. https://driehausmuseum.org/ If you choose the Doubletree one of the best views of Chicago skyline is Navy Pier. I don't recommend NP for anything else really but its free to walk out there and look back at the city. Or you can pay and go up the ferris wheel.

The Art Museum and architecture tours really are great if either interests you.

We stayed at London House Chicago Curio right next to the Magnificent Mile. We would stay there again. Right across from the river and boats that do the architecture tours and close to many, many restaurants. The Nutella Cafe always had a line, just don't get that! We walked everywhere except took public transport to Lincoln Park. What a great city!

I like the Doubletree location a little better for a single female. It has more hubbub going on but I always like the safety in numbers walking home at night. I haven't been inside either one.

I highly recommend the architectural tour river cruise, it is fun and interesting.

For a good view of the city go outside the Planetarium.
https://chicagoimagegallery.cityofchicago.org/Chicago-Skylines/i-M9qzZx9/A

Enjoy!

Thank you very much for your replies!