One of my favorite places to visit in the winter is... drumroll... Chicago! Seriously! I've got the perfect itinerary for a long weekend exploring the amazing restaurants, modern museums, and the snowy city landscape.
We stayed at the Drake in the city, and we loved it. If you're associating the Drake with super high rates, you're not wrong, but as the place ages a bit you can find really good deals... And it still has that grand feeling (ie couch in the elevator)! Also, and maybe most importantly, it's really close to so many activities... so it's highly recommended by us!
Also, we went in 2022 (late writing this up), so masks aren't required inside anymore in most places!
One last note before we get started - once you read and decide what you want to do, be sure to make reservations at everywhere mentioned ASAP (museums, restaurants, escape room, and Blue Man Group). Since we're always doing things last minute, we only booked about a week out, but didn't get our preferred times everywhere, so I'd say earlier is better.
Summary itinerary at the end of the post and all the details right here!
Friday Night: Ice Ribbon at Millennium Park + The Gage
Upon arrival, go straight to your hotel (the Drake) and get changed for a night outside (yup). And yeah it's only a limited time outdoors, but don't let that fool you. If it's winter in Chicago (January, February are the worst) you'll need long underwear, boots, sweaters, coats, gloves, scarves, and hats!
Once you drop stuff at the hotel, take a taxi or Uber to The Ribbon Rink at Millennium Park. Technically it's walking distance... but since we were heading out for the night, I didn't want to waste the kids' remaining energy on a long and cold walk.
You should walk up Randolph and enter the park from there - you'll see a little path down to the rink area. You can grab skates from the kiosk (we reserved skates ahead of time here), rent a locker for your street shoes at the little area inside, and then step out onto the ice ribbon! We spent the majority of the time hanging on for dear life to the railing while slowly dragging ourselves around the loop... but guess what? We loved it. The loop is long enough to be fun but short enough that you can feel completely fulfilled in less than an hour. And the best part is that the skyline views are unmatched!
Once you're frozen solid and before you're all hangry, you need to head to the Gage. Even though it's literally on the other side of the park, you'll want to walk around the edge of the park. That means walking back up to Randolph and then turning south on Michigan Ave... note that I used to live in this neighborhood - trust me on not walking through the empty part of the park after dark. This longer way ends up being about .5 miles... which is maybe 10 minutes without children and definitely 20 minutes with them. So just factor that into your reservation time (and promises of warm food timing).
And why the Gage? I used to live right near here, and I LOVE this restaurant! The food and cocktails are just as good now as I remember when I lived there! We had poutine, burgers, and dessert - and the kids were in heaven. We'd made a reservation ahead, so we had a booth in the dining room. And even though it all felt very adult and trendy (so nice!), they had lids for the kids' cups and the place was loud enough that we didn't feel disruptive. So yeah, we were all loving it. After a long dinner, we headed back to the hotel to sleep!
Saturday Morning: Breakfast* and a Trip to the Field Museum
*Breakfast Note: Alright so - the old version of this post (on Instagram) said to go to Little Goat Diner. It's simply the best trendy brunch spot, and it WAS located in the West Loop (which is pretty easy to get to from the hotel). It turns out that Little Goat Diner has moved up to Lakeview (not as close), so I'm updating my recommendation here! But see the very bottom for my notes on Little Goat if you have time on Sunday!
As a foodie, every meal counts. So I'm going to be picky here. If you're OK with just (amazing) donuts and coffee for breakfast, walk or taxi over to Do-Rite Donuts + Chicken in Streeterville.
(Note: If you want a full breakfast, here are a few more options.
Near the Hotel - There's a chain called Yolk with a few locations between the hotel and the museum with solid diner-type food.
West Loop - If you want the true Chicago foodie feel, I'd recommend making the trek two miles west to Au Cheval. They have a delicious breakfast on weekends, but they don't open until 10am and may have a line. So if that's alright with you, I'd recommend!
River North - If you want fancy, go to Tzuco - which is mostly a modern Mexican restaurant but has a delicious brunch too. We did second dinner here on our trip, and it was pricy but creative and delicious with a cool backstory.
Near the Museum (South Loop) - There are a few restaurants with decent reviews right near the museum... but remember that you won't be saving yourself a ride with this plan because (especially in the winter) nothing is truly "next door" to the museum. The museum is in a huge green space across a major street (Lakeshore Drive) - which makes it difficult to access from anywhere really. But this is an option if you want to at least be close by.
Anyway, if you wanted to overthink food, you now have enough info to do that ... back to the itinerary.)
Next you'll head over to the Field Museum. We actually had Cassie's car at this point, so we parked in the garage at the museum and even got to take a peak at Solider Field (Bears) stadium. But assuming you don't have a car, I'd suggest an Uber/taxi - again, not quickly/easily accessible on foot or public transport.
If you live anywhere outside of New York, Chicago, Paris, etc... you'll be in awe of the Field Museum. Even the building itself, inside and out, is an architectural beauty. And then when you enter, there are a million things to see. I'm someone who rushes through most things (surprise!), but even I could not come close to covering this whole museum in an hour. It's VAST. And every nook and cranny has something special. I'd at least make sure you don't miss the Egypt exhibit in the basement and the Sue exhibit in the back corner of the top floor.
The place is also filled with friendly staff wanting to share their intimate knowledge of super niche areas - and my kids were mesmerized. They also know all the best ways to engage kids (touching a fossil, getting a sticker, petting a squirrel fur... they loved it)!
Get tickets in advance for this too because there are special temporary exhibits that are often pretty cool and sell out quickly. The one pictured above was all about color in nature.
And before you leave, don't forget to stop in the Field Museum gift shop! We had to set a three minute countdown timer (due to a tight schedule and a certain indecisive child) and were still able to find a few special small gifts - plus Sue (the t-rex) paraphernalia galore.
Saturday Afternoon: Hot Dogs, Blue Man Group Show, + El Train
Next, you've got at least a 20 minute drive (a beautiful one up Lakeshore Drive) to the Briar Street Theater.
Get yourself oriented to where the theater entrance is located (so you're not late when it's time!) and then walk about a block south of the theater to Clark Street Dog. Here you can get the quintessential Chicago-style hot dog. What is a Chicago-style hot dog? It's an all-beef frank inside a steamed poppy seed bun. On top is regular mustard, bright green relish, fresh chopped onions, tomato pieces, a pickle spear, and a bit of celery salt. You'd never thought a single hot dog could be so filling!
About 15 minutes before show time, walk back over to the Briar Street Theater to see Blue Man Group. If you're unfamiliar with this show, it's traveled to 25 countries and cities across the US, but it's been playing at the Briar Street Theater in Chicago for about 15 years. It's hard to explain... but it's a group of men covered head to toe in blue paint that do a show full of rock music, comedy, big format art/science experiences... and includes a little audience participation. I was with our (at the time) 5 and 7 year old. They handed out headphones to dull the noise at the beginning of the show, and that was key for these guys - as it was LOUD. But they absolutely loved it! Andrew was talking about it for basically the rest of the year and was definitely his favorite part of this trip.
The next thing we had to check off the list (which is required every Chicago trip) was the El train! The kids LOVE the El. On our first trip to Chicago, they said it was their favorite part and were literally drawing pictures of it at school and home like it was Santa Claus.
Now if you know anything about Chicago, you know there is a decent amount of crime. So when we take the El, we're careful about when we take it and where we are going. (Read: Statistically you'll probably be fine, but as a tourist now, I don't take it at night anymore.)
To me, the best line is the brown line because it's elevated above the Loop and gives some of the best views of the river and the skyscrapers. But the brown line doesn't always fit into our itinerary, so we just make time to get on for a few stops somewhere that saves us time and money within our itinerary.
On this trip, taking the red line from the north side back to the city made the most sense. It was a bit of a walk from the theater (states 6 min so it was really 12), but on the other side it was only a block to the sushi restaurant. It's both elevated and underground at varoius points, so the kids enjoyed that aspect. And the worst you can expect (as long as you're staying aware of your surroundings) on this line at this time are some colorful characters on the train... part of the city experience!
(Note: If you change up the itinerary at all and have a little extra time up here, there are some super cute neighborhood playgrounds around the theater - like Evergreen and Weisman - that you can check out close-ish to the El!)
Saturday Night: Sushi, Donuts, + Escape Room
We read about Sushi San and wanted to give it a try! Chicago has a lot of good sushi restaurants*, and this was definitely one of the good ones!
*Note: Before you say "Sushi in Chicago? It's not near the ocean!"... remember that the key factor is a big airport, and Chicago has one of the largest in the world. Meaning cargo planes bring fresh fish faster here than most coastal cities... so yeah - awesome sushi in Chicago!
We actually went pretty early so that we could still make our escape room, and that made it easy to get a reservation at Sushi San. The restaurant is focused on sushi and the fish is so good! We got edamame for the table and then rolls for each of us. Andrew wanted to stick with more of a kids roll (avocado), and Molly got a California roll. I got a play on a spicy tuna roll that was recommended by our waiter. Also sake. :) The place is "hip", and it started getting really busy as we were leaving - so definitely book in advance!
Once we well fed and warm again, we walked across the river and through River North toward he escape room! We had to make a stop at Firecakes Donuts on the way (can't skip dessert!), but honestly they didn't have a sit down area... so not sure I'd recommend walking and eating donuts when it's 10 degrees outside... but we made it work!
And for the escape room, there are plenty of options, but we really LOVED The Escape Game Chicago. The rooms were difficult (which is what makes it so fun, right?) and the staff were exceptionally nice. Molly was not super into it after a bit (scared), and they actually took her to the control room, gave her a fake staff badge, and let her watch us trying to get out... this turned what could have been the most tramatic part of the trip for Molly (5 at the time) into the absolute best! They even wrote her a little card thanking her for being part of the team, and she still has it today!
Andrew (6 at the time) on the other hand was absolutely loving it. He was helping us solve the puzzles and could even physically participate in it (like lassoing something or moving magnetic puzzle pieces)... all the things.
After all that activity, we were ready for bed! But if you still have some energy to burn and want to leave the kids with a sitter while you hit the town- message me for recommendations! :) On sitters. I also have some really good dive bar recommendations if that is your thing! ;)
Sunday Morning: Brunch in Lakeview!
Ok so before you head back to the airport on Sunday, go to Lakeview! It requires a stop on the way to the airport, but it's worth it just for the food. Our favorite breakfast place (mentioned above and pictured right above) is Little Goat and worth the stop every time!
Hopefully you know by now that you can trust me when it comes to food and restaurant vibe, and I'm telling you that you need to go to Little Goat. It has great food and a hipster vibe, but it's also super kid friendly. Even though it's focused on breakfast food, it's actually open for breakfast, lunch, and dinner, and we've been for all three. But we were determined to have a Saturday morning breakfast there, so we booked in advance. They're used to kids, and they'll pull out the stops (custom cups, crayons, and you know… breakfast food!!) while also catering to foodie adults - and even a photo booth! Of course some of this may have changed in the move (as they are opening late Spring 2023 so we don't know yet)... but the owners are the same and I trust they did it right!
In terms of other things around there, you'll be right in 'Southport Corridor", which is a trendy few blocks full of shops and restaurants. I think most of the shops are chains at this point, but they are good ones at least. So if that is your thing, walk around and shop before you head out. Also (or instead) don't forget that you're right next to Wrigley - the Cubs stadium! Obviously if this is a winter itinerary, you won't be going to a Cubs game, but it's still worth it to see the place (and stand outside in front of the entrance for a picture).
And that's a wrap on your winter weekend in Chicago!! Don't forget to plan ahead - make reservations and bring warm close - and you're guaranteed to have an awesome time!!
As always - something we didn't do this trip but would have been fun: the Children's Museum at Navy Pier. When we were there it was still closed for Covid (yeah in 2022...), but it seems to be open now and is a blast!
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