What to Do in Chicago in Winter

Visiting Chicago in winter is a great idea. Go in November, when you’re kinda in between the main Christmas run, and at the end of the warm weather visitors – so you get the best deals on hotels, the streets are quieter, and you still get to soak up a little Christmas spirit without having it shoved in your face.

Visit mid-November and you’ll also get to experience the Magnificent Mile Light Parade – more on my part in the 2018 edition in a bit.

View over the Chicago Skyline

I can’t actually believe how good the prices of flights from the UK to Chicago are in winter. Think: around £275 return. You can check out the latest deals on Skyscanner. It’s an 8-hour flight and only a 30-minute taxi ride into the city, or 1 hour on public transport.

It’s pretty easy to get there from London, meaning that a winter weekend in Chicago isn’t totally out of reach. So, logistics out of the way, let me take you through the best Chicago winter activities to get you excited.

Visiting Chicago in Winter

Of course the best thing to do on those wintry days in Chicago is to eat. You need to keep your energy levels up team, and with so much choice in the windy city, make the most of it.

Breakfast in Chicago

Lou Mitchell’s

For breakfast I’d suggest Lou Mitchell’s. The traditional diner has been going since 1923 and serves up one of the biggest breakfast menus I think I’ve ever seen. Kinda gives a clue to the portion sizes though – pancakes bigger than your head, piled on top of each other.

Chicago Lou Mitchells

Lou Mitchell's breakfast in Chicago

I went for eggs, bacon and potatoes served up in a skillet. It was the cinnamon toast that came with it that was the absolute star though. It was delicious. So buttery, and cinnamony, and soft… and… I need to eat it again one day.

Lou Mitchell’s is right at the start of Route 66, so if you’re in Chicago for a winter road trip, it’s the place to fuel your body.

House of Blues Gospel Brunch

Best Brunch in Chicago

The other great option for breakfast in Chicago is the Gospel Brunch. You can get an all-you-can-eat buffet at the House of Blues, complete with all-you-can-drink mimosas. During the two-hour sitting you’ll be entertained by a gospel choir and their hilarious choir master. Make sure you sign your mates up for the dancing competition beforehand. Only tell them when their name is called though, just for fun.

House of Blues Gospel Brunch

This was a brilliant start to a Sunday, and the chicken and waffles were sensational. After being confused by the popular combination for years, I’m now a convert.

Lunch / dinner in Chicago

After an epic Chicago-size breakfast I’d recommend you pick lunch up on the fly. See how hungry you are. The restaurants I’m about to suggest for dinner, can be for lunch too. But with the portion sizes I’d recommend saving yourself so you’re hungry enough to go all out when you get there.

If you need feeding in between, pick up some Garrets Popcorn, an Al’s Italian Beef Sandwich or a Portillos Hotdog – all Chicago icons for a good price.

Harry Caray’s

Dinner in Chicago

Harry Caray was a legendary sports commentator from Chicago. The chain set up in his name Harry Caray’s is a staple on the Chicago restaurant scene, with branches all over the city. The serve smoked meats, huge salads and massive burgers. The restaurants are decked out with movie and sports memorabilia and the celebs love the place.

I went to the one at Navy Pier, where the Obamas had been a few months previously, as the pictures proved. They had a special section devoted to Bill Murray’s film clothes. Sent pics to my boyfriend – jealousy levels through the roof apparently.

Ginos East 

It’s a big pizza pie! You can’t really call the pizzas served here ‘pizzas’. They are HUGE. To put it in perspective I only managed one slice.

Me! Vicky One Slice!

Pizza in Chicago

I went for the spicy sausage option which seemed to have an entire slab of sausage in it, rather than the sprinkling on top that I’d pictured. We had so much pizza left over.

Really cool place though. It’s covered in graffiti which you’re totally welcome to add to. See if you can find the ‘VickyFlipFlop’ somewhere.

Labiola

This Italian restaurant is right in the centre of town, by the Riverwalk. Again, huge portions.

Dinner in Chicago

The lasagne looked like it’d feed a family of four. I went for the salmon, which was big, juicy and delicious. But it was the desserts that excelled. Look at that display. Apparently it was for the table. I’ll admit I ‘sampled’ quite a few of them. Waste not want not.

Elephant and Castle

Who doesn’t want a traditional British pub when they visit Chicago? Ok, random choice. I was in a big group for my wintery visit to Chicago, and so unfortunately they shoved us downstairs with a chicken buffet. The food was decent though and up top there was a great Saturday night atmosphere. Apparently the fish and chips here are delicious. 

Winter activities in Chicago

Right, you need to earn all that food. Let’s take a look at what you can do in Chicago to burn some cals.

Museums in Chicago

Visiting Chicago in the winter

Chicago has SO many museums, all providing the shelter you need from a cold wintry day in Chicago. Get your hands on a Chicago CityPASS for just over $100 and you’ll get VIP or fast pass access to:

1. Shedd Aquarium – PRIORITY ENTRY

2. Skydeck Chicago – FAST PASS

VickyFlipFlop up the Skydeck

– go to the SkyDeck and you can look out over the city, and down to it too. 

3. Field Museum – VIP ENTRY

4. Adler Planetarium – VIP ENTRY OR Art Institute of Chicago – FAST PASS

5. Museum of Science and Industry OR 360 CHICAGO Observation Deck – EXPRESS ENTRY

If you want a little festive spirit in your life you should also check out the Museum of Science and Industry. The humongous building has a 40-strong ‘Christmas trees from around the world’ exhibition for the season.

Museum of Science and Industry

Although, the British one was decorated with a photo of the Royal Family, a photo of Kate Middleton holding baby Louis and a veil draped over the top, so I’m not entirely sure how accurate the other representations are of a traditional Christmas.

The museum was great though. I went in a room designed to be like a womb and learned all about what it was like to be a foetus. Errrr, took me right back.

Magnificent Mile Parade

The Magnificent Mile Parade, one of the main reasons for me visiting Chicago in winter, was awesome. Over a million people turn out for the parade down one of the most famous shopping streets in all of America.

Waving flags in the Magnificent Mile Parade

This year, 2018, I was stood on top of the Illinois Tourist Board bus with about 20 other bloggers from around the world, waving the UK flag I was given at the crowd. There were tens of floats ahead of us, and right at the front Mickey and Minnie Mouse were turning on the festive lights with their wands. It was broadcast on ABC all over the US.

Look carefully and you can see me in this video at 10:15 onwards. I’m in the middle waving the British flag high.

What an experience!

If you time your winter trip to Chicago right, you could be there for the Magnificent Mile Parade, and then for the annual Thanksgiving Parade a few days later. Wrap up warm!


READ MORE: Your Winter Holiday Packing List


Go and see a show

See what’s on at the Vic Theatre, or the Chicago Theatre. There are Christmas productions and other ones throughout the season. When I went to Chicago in the summer I did this and oh my god, Beyonce was playing. Bagged myself one of the last remaining tickets and had a brilliant night at Soldier Field.

This November Chicago visit, I went to see the famous Blue Man Group. Gawd it was weird. Three men dressed in blue spitting out marshmallows, eating Twinkies and spewing them out, making pictures out of paint, and drumming with neon colours. It wasn’t quite for me, but it’s one of the most iconic things you can do in Chicago – and it was lovely and warm.

The architecture tour

Look up in Chicago

I’ve been recommended by a few people to do the architecture tour. I think it’s one of the best things to do in Chicago, and so far I’ve missed out but just wanted to include it for you.

Millennium Park and The Bean

Go for a walk in Millennium Park to see the most photographed bean in the world: The Bean. You’ll find the die-hard selfie lovers in here, all taking a pic with the skyscrapers reflected in the background.

Can you spot me among the bloggers? 

Bean in Chicago

Grant Park

And then walk to Grant Park. It’s right near most of the museums on the Chicago CityPASS, so combine that in your Chicago itinerary.

Chicago Grant Park

Winter views of Chicago

The 360 and the SkyDeck are the two main places to visit to enjoy a view of the Chicago Skyline in all its winter glory.

One of the insider tricks though, is to go up the Hancock Building at 875 Michigan Avenue. Go up to the 96th floor and you’ll reach the Signature Lounge, free to enter but pricey drinks, and enjoy a view out to Chicago. I tried to do this but the queue was too long for the time I had. Make sure to leave plenty of time.

Chicago skyline vickyflipflop

Chicago winter walks

I was there mid-November and although it was definitely chilly (think 1C-ish) on the last day of my trip the sun was out and the sky was blue. The perfect fresh weather in my opinion.

The temperature in Chicago in November was pretty chill, but I think as long as you’ve packed some snug boots, some good socks and a thick winter coat, you’ll be alright. I wouldn’t say it was freezing, and nowhere near as cold as New York in December. Don’t think I’ve ever been so cold in my life.

Go and visit one of the 77 neighbourhoods

Chicago is made up of 77 neighbourhoods and if you ask any of the locals where the best places to hang out are, they’ll usually reply with one of those – not the centre of Chicago. It’s like London. Tourists go to Oxford Street and have a lovely time, while the locals go to Brixton and Dalston, or wherever the cool place is now.

When I was in Chicago for the summer I hung out in Lakeview. Another place I’d definitely recommend – I even managed to find a Beyonce yoga class.

Armitage

Visting Chicago in winter

I took the brown line to Armitage, in the direction of Kimble, and had a look at the little shops and boutiques there.

From Armitage it was easy to walk to Lincoln Park. This gave me a good opportunity to check out some of the houses, and buildings – the architecture of Chicago is one of its main attributes. And once you get out of the hotels and apartments of Downtown, you get to see the houses, where people actually live.

I walked through Lincoln Park, through the zoo and down to the Magnificent Mile.

Chicago Armitage

Pilsen

If you have time go and visit Pilsen – it’s the Mexican area of Chicago, complete with amazing tacos and cool street art. Apparently the latest up and coming part of Chicago.

Christmas in Chicago

If you’re going to Chicago in November you’ll want to do something Christmassy, right?

Macy’s Tour

Macy's Tour

We joined a tour round Macy’s to learn more about the store and how it prepares for Christmas. You’ll be taken round the store and shown how they prepare for the festive season. Also, given some background on the history of the store, and titbits on the women who’ve shopped there for years. If you like glitz, shopping and Christmas trees, this is the tour for you.

ChristKindl Market

ChristKindl Market

Chicago’s German-style Market the ChristKindl Market is located around the Picasso sculpture in the city. Visit and you can sip on mulled wine while checking out all the trinkets. There’s also loads of different foods to buy and an indoors bar to escape the chilly weather. I warmed up on mulled wine. All good.

Christmas shopping in Chicago

The Magnificent Mile is the key place for shopping in Chicago. You’ll find all your high street favourites peppered down the route. Visit after the Electric Lights Parade and you’ll also have the Christmas Lights to see too.

Shopping is one of the best things to do in Chicago in winter because, obviously, the shops are nice and warm. There are some indoors shopping centres for especially cold or rainy days – check out the Shops at North Bridge for starters.

Where to stay in Chicago in winter

You can get some great bargains in the hotel world if you’re looking for Chicago accommodation in the winter. I stayed at the Holiday Inn, which was nothing like the Holiday Inns I’ve stayed at in England.

View from the Holiday Inn

It was perfectly positioned downtown by the river. The hotel doesn’t actually even start until floor 15, so you know you’re going to have some impressive views over the city.

There’s a pool, a cafe, a shop and a restaurant on site. My bedroom was big, with a huge bed, a fridge, and a welcome platter of meats and cheeses, which is always appreciated.

If you want somewhere more boutique, try the

Getting around Chicago in winter

I got around Chicago by Uber most of the time. It was pretty cheap – cheaper than England. If you have time though, I’d strongly recommend you just walk. Chicago is such an easy city to walk around, thanks to the fact that it’s built in squares and so easy to map read.

Waiting to ride the L Train

I also used the L Train for a few journeys and found it easy and safe. This was the best way to check out the neighbourhoods away from the heart of the city. I felt SO ER, travelling on the trains. Loved it.

Chicago in WInter

Chicago in winter, next time

Next time I visit Chicago I’d like to eat a hotdog, eat at Lou Maltinis, go to a baseball game, explore more neighbourhoods and go up to the Signature Lounge too. Oh and I’d totally go ice skating in Millennium Park too.

If you have any questions about travelling to Chicago in the winter, just let me know in the comments box below.


I was in Chicago, Illinois thanks to Enjoy Illinois, the Illinois Office of Tourism. I received visits to most of the above in return for a review and a mention in my travel blog. If you’d like to find out more about Illinois, just click this link.


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