Late Fall Chicago Travel Guide

Today I’m sharing my Late Fall Chicago Travel Guide. Everything you should do in Chicago during late fall!

Hi guys! Today I’m finally sharing my Late Fall Chicago Travel Guide and everything we did and where we ate when we visited Chicago a couple weeks ago. We had the best time and I’m so excited to share with you.

Geoff and visited Chicago the first weekend in November. We both took Monday off and had a long weekend. He turned 35 at the end of October 😳 so I thought it was necessary that we celebrated it up big! 35 isn’t a milestone birthday per se, but it felt like it to me. I had been looking at flights for what felt like a month and there wasn’t really anywhere in particular I was looking. Most of all, I wanted it to be a place we hadn’t visited together before.

I ended up finding really cheap flights to Chicago – I think they ended up being $50 each on the way there, and then the return flights were $100 or so each. Love finding those JetBlue flight deals! I also got TSA pre-check very recently and my first time using it was for this trip so that was exciting.

Sweater // Coat (from TopShop last year, linked similar) // Jeans
// Boots // Sunglasses // Handbag (sold out but linked similar) //

Anyways, from everything I read about Chicago it said that the best time of year to visit is summer or early fall. November for Chicago is more like late fall, almost winter since it gets so cold there. The day we arrived it was pretty chilly but the weather warmed up a bit during the week so it wasn’t terrible weather. I would probably avoid January/February/March just knowing how cold it is in Boston during that time and I know Chicago is even colder.

Late Fall Chicago Travel Guide

We had the BEST time in Chicago. I had planned so much, knowing full well we wouldn’t be able to get to everything on my list but it’s good to save some things for a future trip. I would 100% go back to Chicago! Definitely would love to travel there during the summertime or September when it’s still warm so that I could take advantage of all the outdoor dining, rooftop bars, and maybe a little boating. Also, if you’re in need of a girls trip, Chicago would be such a great destination.

What immediately stuck out to me about Chicago is that it feels like the perfect mix between Boston and New York City. Bigger than Boston and trendier, but not as crazy as New York City. Anyone been to both? Thoughts?!

Where We Stayed in Chicago

Chicago has TONS of amazing hotels. Hopefully I don’t sound too crazy but I initially made a spreadsheet of about 15 different hotels in Chicago to narrow down where we wanted to stay. We wanted to be close to downtown and in the middle of everything so that we could walk everywhere. We like a boutique, modern feel when picking a hotel. We also wanted something reasonably priced. I was initially drawn to The Langham – it seriously looks gorgeous and I believe it’s rated #1 hotel in Chicago but it was a bit out of our price range for this trip.

I’m not kidding when I tell you I was researching 15+ hotels before finally deciding on St. Jane. It had basically everything we were looking for. It’s modern and has an amazing design – how gorgeous is the lobby? It was also in a great location, affordable and had both a coffee shop and restaurant attached. Geoff got a coffee one day but we didn’t eat there. Regardless, it’s nice to have the option if you eat dinner at a weird hour or get a late night craving 😊.

Also – we got to Chicago so early because we had an early flight. We went to St. Jane intending to just have them store our bags so we could go out and explore without them, but they let us check in early at around 11am. So nice when hotels let you do that and it made the stay feel a little bit longer!

Where We Ate Brunch in Chicago:

The Dearborn
We ate at The Dearborn our first day in Chicago. We landed in Chicago very early so we were excited to find The Dearborn close by to St. Jane where we were staying and it opened fairly early at 10am on Saturday which was nice because we were starving! The Dearborn was classy without being even the slightest bit pretentious which we liked. It would be the perfect spot to take your parents for brunch if they were visiting. Not overly trendy, beautiful interior, and amazing service.Seriously I think the service is what made The Dearborn so memorable.

I wish I could remember our waiter’s name but he was one of the best waiters I’ve had at any restaurant ever. Chatted about why we were in Chicago and we explained that it was for Geoff’s birthday. He gave his recommendations on places we should check out and what is overrated/what we could skip. He even brought out a piece of birthday cake on the house. Best service and great brunch! Get the egg sandwich and they also had really good coffee (or maybe I was just really exhausted 😂 but I swear it tasted so good haha).

Summer House Santa Monica
Ahhhh best brunch of the Chicago trip. If you think of everything that makes a brunch spot so great, well, Summer House Santa Monica checked off every box. It’s beautiful inside (definitely grammable) and had great menu options (both food and drinks). They also had turquoise and white Yeti coolers everywhere with rosé and prosecco inside which was what the waitstaff grabbed if they needed to make a quick mimosa or pour someone a glass of wine. They also have a board that marks how many days till summer. It’s those types of unique touches I love about a place and make it stand out.

Also loved that Summer House Santa Monica has a little café as you first enter the restaurant where you could come in and grab coffees, pastries, cookies, etc. if you just wanted to grab them and go – or you could order a little something to hold you over while you wait for your table like I did. Definitely get the La Calombe draft latté and the fruity pebbles rice crispy treat while you wait for your table. Both were SO good. The name Summer House Santa Monica felt so fitting – there’s bright white interior with greenery everywhere – you immediately feel like you’re in California – even if it’s freezing outside!

3 Arts Club Café at Restoration Hardware
Brunch at 3 Arts Café at Restoration Hardware is a must when in Chicago! If you’re not familiar, 3 Arts Club Café is a brunch spot located on the first floor of Restoration Hardware in Chicago. Restoration Hardware has always been the epitome of decor goals to me. Everything is so well made, classy, and luxurious. I’ve been wanting to splurge and buy a few of their towels (they’re so good).They take reservations which is nice since I’m told it can be hard to get in on the weekends. We made a reservation and went on a Monday and it was fairly empty. Get the truffle grilled cheese or the burger (I’m told it’s the same world famous burger that Au Cheval serves).

Where We Ate Lunch in Chicago:

Lou Malnati’s
Trying authentic Chicago deep dish pizza was at the top of my list for things we needed to do while in Chicago. Those who are local to Chicago seem to be very split on where you can get the best deep dish pizza in Chicago (the other favorites are Giordano’s and Pequod’s. Based on what I read, I thought we would like Lou Malnati’s the best. Definitely enjoyed it but this is a heavy slice of pizza. I’m pretty sure I ate one slice and then was stuffed 😂🙈. It probably wasn’t my favorite pizza in the entire world but it was good and it’s a must while you’re in Chicago!

Appetizers/Drinks in Chicago:

Fisk & Co.
Any spot that serves wine and seafood will immediately make me feel at home – it’s just the New Englander in me. This was another spot that was close to our hotel so it was very convenient. We had been eyeing it every time we passed it during our first day we were in Chicago and decided to stop in for a couple drinks and appetizers the next day. Have a glass of wine, get the coconut curry mussels, and the frites with roasted garlic aioli. I swear all I need to be happy is a glass of wine and some fries 😂🙌🏻.

Parlor
My friend Kara described Parlor as the Lincoln of Chicago and the description was spot on! She has an awesome Chicago Travel Guide here. We checked out the West Loop location around 7ish I think and it was packed. If you’re single and going out for drinks in Chicago I would start here because it was definitely man-heavy haha. You’re bound to meet someone  😜. I didn’t get any photos but this restaurant was big and had a large, square-shaped bar with people sitting on all sides. I would strictly go for drinks.

Bandit
Is it possible to fall in love with a bar? Because I did when we went to Bandit. This is like 90s kid dreams in a bar haha. We went Sunday night so it was fairly quiet in terms of it not being packed because most Chicagoans were probably getting ready for the work week. When we walked past it the previous night, it was a Saturday and seemed vey busy. This place was just plain fun.

They played old school Tupac, Biggie, Drake, Kanye, etc. Pretty sure Geoff and I would have spent all night here but we felt guilty to keep the bartender hanging around because it was a Sunday night haha. We also watched the Patriots here since they were playing that Sunday night. Also – I have to touch on the bathrooms. The women’s bathroom was covered in an N*Sync collage and was playing N*Sync music. Geoff reported back that the men’s bathroom had Britney Spears everywhere haha. So fun. Ps. Get the “Shady Lady” cocktail!

Centennial
We went here for beers after going to Summer House Santa Monica for brunch. Wouldn’t be my top choice but if you need a place to make your man happy after he goes to a couple Instagrammable brunch places with you, then this is your spot. They had a great beer list.

LondonHouse Chicago
Great views for drinks! We went on an afternoon but I bet the view is even more gorgeous at night.

Where We Ate Dinner in Chicago

Leña Brava
We went to Leña Brava on Saturday night after trying to go to The Girl and the Goat and couldn’t get in. I went into this meal sort of disappointed because it wasn’t initially where we wanted to go but it was delicious. I’m not huge on mezcal so I didn’t love my drink (my fault because I wasn’t paying attention when I ordered), but the wine and seared scallops were delish!

The Girl and the Goat
A must when in Chicago! We had tried to go here Saturday night and wouldn’t have been able to get a table until 10:30 so we decided to skip it and try to go Sunday. Definitely try to make a reservation if you can. We made an early reservation for around 5pm on Sunday instead.

The Girl and the Goat specializes in tapas and you guessed it – tapas that have goat in them. We were a little bit nervous to try but ended up getting the Confit Goat Belly and it was delicious. Now we can say we’ve tried goat haha. Anyway, this was such an incredible meal. The atmosphere sort of reminded me of Barcelona Wine Bar that we have here in Boston.

Get the shishito peppers, the bar harbor mussels, the seared scallops, the wood fired whole branzino (somehow there were no bones in this!). Everything was so delicious.

Other Restaurant Recommendations We Didn’t Have Time For:

• The Hampton Social– drinks/brunch (home of the infamous Rosé All Day sign
• Little Goat Diner– brunch
• Au Cheval– lunch (best burger in Chicago apparently)
• Beatrix– on the healthy side!
• RPM Italian– dinner
• Mad Social
• Purple Pig– dinner
• J Parker Rooftop– drinks
• The Allis at Soho House– brunch or drinks
• The Vig– drinks
• Portillo’s– Chicago style hot dogs
  
  

What to do in Chicago

I have to preface this by saying I think all we did was walk around and eat this whole trip haha. But we really enjoyed it. If we were to go back again soon here’s what else I would add to my list!

• Architecture Tour
• Skydeck Chicago
• Shop on Magnificent Mile
• Walk around the Gold Coast
• Check out Utopian Tailgate (late summer, early fall)
• Revival Food Hall
• The Signature Room at the 95th – like the Top of the Hub in Boston
• Go to a Cubs game (summer or early fall)
• Museum of Contemporary Art
  
  
  
  
  

Hope you guys enjoyed my Late Fall Chicago Travel Guide! Have you been to Chicago?! Any favorite spots I missed? Let me know in the comments! 😊❤️
If you enjoyed this post, you’ll also enjoy Boston Travel Guide: The Local’s Guide to Boston Massachusetts, Getaway House: A Weekend Escape From Boston, and Fall Recipes I’m Excited to Make + New Home Items.