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!

The architectural boat tours are great if your feet get tired.

The art museum is fantastic - closed on Mondays - but not a long walk from the river.

Going to the top of the Willis tower will give you a view down onto Chicago that is expensive, but kind of interesting. I skipped this my first few visits, but finally did it. Cheaper and fun is the ferris wheel at Navy Pier. And, on the architectural boat tour, the go far enough towards the lake that you get a decent skyline view.

We also enjoyed sitting in the Adirondack chairs on the grass at the point where the river walk ends and the river splits.

I read your title and started salivating thinking of their authentic Chicago pizza! Oooh! But I don’t see it on your plans.

Pizza--since I am going solo, I don't have anyone to share the pizza with. My SO loves Chicago style deep dish pizza and I will share one with him whenever he gets a chance to travel with me.

I will use public transportation to reach the airport.

O'Hare or Midway? The Blue Line (O'Hare) has extremely poor service since the pandemic. I wouldn't want to rely on it to catch a flight. Give extra time if you must.

is Portillo's really that good?

20 years ago. Too many locations now so not really special Chicago thing anymore. I prefer Al's over Mr. Beef. But Mr. Beef has "The Bear" tie-in now.

Hubbard Street has a really good restaurant scene.

Thank you for the info about the Blue Line. I will fly into and out of ORD (Alaska Airlines). Do you suggest using Uber or Lyft? I am worried about road traffic jams.

Definitely take the train in from O'Hare (you're in no rush) and just leave earlier than normal heading to O'Hare. Worst case, walk to Blue line station and if there's a long wait for the train, take Uber instead.

I took the Blue line to the airport, no problems at all. You can look online at the CTA website to see if there are system issues so perhaps do that a few hours before your flight. My relatives that live in Chicago recommended taking the Blue line to the airport. From River North I took a bus a few blocks and then walked into the Blue line station; Google Maps showed how to do it which was helpful because some of the Blue line station locations are not obvious (they don't have the same large signage you see in NYC)

As for pizza, Lou Malnati's has individual size pizza as well as larger pies. There's one right next to the Wrigley building near where you'll be staying in River North. It's quicker to get seated for one person if you sit by the bar instead of at a table.

I think the Blue line is fine, our kids just used it for their trip in May. If your flight is on a weekday, the rush hour traffic will be getting bad so an Uber will just sit in traffic. Is your flight at 5 or is that when you have to leave for the airport?