2 days in Chicago and why you have to visit in the fall

2 days in Chicago and why you have to visit in the fall

Part-Time Passport

Part-Time Passport

Welcome to Part-Time Passport! Here you'll find destination inspiration and travel advice on how to balance work and home life with serious wanderlust.

When you think of honeymoon destinations, it’s probably fair to say that Chicago doesn’t immediately spring to mind… especially in November. 

But 2 years ago, that’s exactly where me and my hubby were headed for 2 days to kick off our honeymoon celebrations, before moving on to a far more predictable destination for sun-seeking newlyweds… Hawaii.

Yet despite visiting paradise (literally), Chicago came up trumps as our favourite destination of the honeymoon and somewhere we’ve even talked about moving to one day. I loved every thing about this beautiful city – the grandeur of the architecture, the buzz of downtown and the absolutely stunning fall foliage, which framed every angle of the city in early November.

When I returned to the UK and shared my photos, I was amazed at how many people commented how “surprised” they were at how attractive the city looked and that it was nothing at all like they had imagined. It dawned on me that this this is a seriously misunderstood and under-rated city and I’ve been desperate, ever since, to showcase just how spectacular Chicago really is – especially in the Autumn.

Getting there

It’s an 8h30 direct flight from London to Chicago O’Hare airport, making it just about do-able as a short-break option for Brits looking for an alternative to New York or Miami. Return flight prices start as low as £350 with Norweigan Air , or even cheaper if you’re willing to make a quick stop in Montreal on the way. Autumn is a great time of year to bag more affordable fares, after the rush of summer tourism has passed but before the chills of winter have set in.

Top tip: Be careful to avoid the week of Thanksgiving (the fourth Thursday in November) when prices can sky-rocket.

Where to stay

There are a number of well-known areas to be aware of when booking your stay in Chicago. The Loop, River North and the Gold Coast are all popular choices with tourists – but they come with a hefty price-tag.

Instead, I would recommend staying in the Lincoln Park neighbourhood, situated on the edge of Lake Michigan and just a few miles north of downtown. Here, you’ll find cheaper accommodation and a much more authentic, local vibe. Lincoln Park and its neighbouring ‘Old Town’ district are worth a visit in their own right, whilst all the attractions of downtown remain easily reachable by bus or Uber.

We stayed at The Hotel Lincoln – an artsy, boutique hotel located directly opposite the park with spacious rooms and an AMAZING rooftop restaurant and bar – the J Parker Lounge – with spectacular views of the Chicago skyline. The staff at the hotel were so friendly and the views from the room breathtaking, with the autumn leaves in full bloom. There’s also a great coffee place called Elaine’s in the foyer of the hotel, which is perfect for a coffee and bagel to-go, as you head out to explore the city each morning.

2-day Chicago Itinerary

We would have loved more time to explore The Windy City but 2 full days is just about enough time to experience some of the main highlights of the city and to get a feel for what Chicago is all about.

Day 1:

Start your day off in one of the city’s most impressive green spaces – Millennium Park. Here, you can admire the fascinating array of sculptures and public art on display, including Cloud Gate – the world-famous, giant, steel bean, which proudly reflects the city skyline in its reflective surface.

Be sure to look out for Crown Fountain, with its giant interactive video displays and water features, and don’t miss the stunning architectural design of the Pritzker Pavilion, set in the grounds of the park.

At this time of year, the autumn leaves were out in all their glory, making for a perfect leisurely wander around the park.

For brunch, head to Wildberry Cafe on the edge of the park and and order one of their famous pancake stacks. Just be prepared for a serious sugar crash in T-minus 2 hours!

There really is no better way to appreciate Chicago and her magnificent skyline than by water. For your next stop, head towards the river and board the Chicago Architecture Foundation boat cruise for a truly unique perspective of the city. You don’t have to be an architecture buff to appreciate this fascinating 90-minute narrated tour of how the Chicago skyline came to be – this is the city that gave us the first skyscraper, after all!

This is a great thing to do on your first day in Chicago to get to grips with the layout of the city, before you head out on foot. 90 minute tours will set you back by approx $45 pp or sunset and dinner cruises are available for slightly more, if you want a truly special experience.

Once you’re back on dry land, head downtown to explore The Loop and the endless rows of boutique shops and department stores along The Magnificent Mile. 

As the afternoon sun begins to fade, make your way towards one of Chicago’s most famous landmarks and one of the tallest buildings in the city – the John Hancock Center. 

The 360 Chicago Observation Deck located on the 94th floor is one of the most popular tourist attractions in Chicago but I’d recommend you skip the $20 entrance fee and, instead, head straight up to The Signature Lounge at the 96th floor for a cocktail, complete with the most breathtaking panoramic view of the city and Lake Michigan below. This is truly a “must-do” Chicago experience and you can’t help but fall in love, as the sun sets and the city lights up before your eyes.

(Top tip: one of the best unobstructed views is actually from the Ladies Toilets, so be sure to take a peek!)

Once you’re back on solid ground, head back towards Lincoln Park to sample one of Chicago’s signature dishes at Chicago Pizza & Oven Grinder. As well as serving up some of the best pizza pot-pies in the city, this charming restaurant also has its own little slice of history: the building is located directly opposite the site of the St. Valentine’s Day Massacre; the infamous 1929 murder of rival gang members by Al Capone’s men.

Top off your first night in the city by heading to the J Parker Lounge rooftop bar, where you can relax to the lights and sounds of the city around you.

Day 2

Plan to spend your second morning around Chicago’s largest park and one of most tranquil spots in the city – Lincoln Park. There’s really nowhere quite so serene and beautiful, especially when cloaked in the autumnal hues of November. You could easily pass an hour just wandering through the leafy trails – or, if you have time, be sure to stop by Lincoln Park Zoo – a free attraction, located in the centre of the park.

One of the best things about Lincoln Park, is its location just north of the city, providing unparalleled views of Chicago’s world-famous skyline. From here you can see the whole city laid out in front of you – and it’s pretty spectacular!

Just a short walk from the park is the Old Town neighbourhood – a charming, historic district packed full of cute, boutique stores and kitsch cafes. This is the perfect place for window-shopping along the tree-lined streets and a quick lunch stop in one of the many eateries.

After lunch, head to Navy Pier – one of Chicago’s most recognisable landmarks – and take a spin on the Centennial Wheel for 360 degree views of the city ($15 pp for tickets).

Walk along the lake-shore past Buckingham Foundation and Grant Park, taking in the sweeping views of Lake Michigan to your left. You’ll eventually arrive at Chicago’s cluster of world-famous museums and attractions, including The Field Museum, Adler Planetarium and the Shedd Aquarium. Spend the rest of your afternoon indulging in a bit of culture, before heading back downtown for dinner.

If there’s one thing you absolutely MUST do in Chicago before you head home, it’s experience some live blues. Blue Chicago, located in the River North district, features world-renowned live blues acts every night. It’s $12 on the door, and you’ll be lucky to get a seat in this crowded little bar, but it’s worth every cent to experience the soulful sound of Chicago blues, in the city where it was born.

If you have more than 2 days…

We only scratched the surface of Chicago in 2 days and are already planning a return trip to explore more of this enchanting city. If you have some extra time, consider adding some of the following activities to your itinerary:

Hire bikes and cycle the 606 

Cycling is an excellent way to see the city in all its grandeur and there are beautiful, scenic trails all along the lake-shore. The 606 is a brand new development, bringing together arts, history and design for locals and tourists to enjoy. Cycle along the paved trails and enjoy the pretty parks and paintings along the way.

Make the most of Chicago’s beaches

Yes, believe it or not but Chicago has miles of beautiful beaches, all along its lakefront. North Avenue Beach is one of the most popular and is a great place to relax in the city with stunning views of the skyline.

Take a food tour

Local food tours are fast becoming one of my favourite things to do when travelling to any new city and the Chicago Food Planet Tour offers a wide range of walking food tours, taking in the very best dishes that Chicago has to offer. I’m not sure we made the most of Chicago’s food scene during our first visit, so this is definitely on my bucket list for when we return!

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