Chicago City Guide

MileNorth Hotel
Whilst in Chicago I stayed in this boutique hotel. Located Downtown, it's just off the famous shopping street Magnificent Mile. The staff were really friendly and my room was insane. I was very kindly put up in a suite and it has to be one of the biggest rooms I've ever stayed in. It's even the proud owner of a rooftop bar - sadly it wasn't open for the season when I was there. The bed was massive and I slept like a baby all three nights. I'd really recommend this if you're ever in the city.

Wicker Park
If you've got a soft spot for second hand shopping, this is your neighbourhood to visit. It's got an abundance of vintage shops - some are quite pricey - alongside the famous consignment stores Crossroads and Buffalo Exchange. It's around $13-14 for a cab journey each way. Make sure you grab a bite to eat at Dove Luncheonette - well worth the queue!

The Signature Lounge at the 96th
The views from the top of this bar will blow your mind. I'm a sucker for a good view and this one is gorgeous. It's well worth the price of the cocktail to be greeted with that sight. Go at night and the city is absolutely stunning. It was one of my favourite parts of the trip. Try to go during the week and fairly early to avoid the queues. Keep in mind they don't take reservations.

Skydeck Ledge
The unique selling point of the Willis Tower is it has an impressive glass ledge that extends out 4.3 feet. It's such an odd experience to step out and peer down such a staggering drop. My legs felt like jelly as I tentatively stepped out but it was such an amazing feeling. It's the tallest building in the western hemisphere at 1, 353 feet. Definitely something not to be missed!

This strip is full to the brim of LGBT bars and clubs. We only went out to one bar and stayed a little while because we had a band to catch. But it looked like it would be such fun and I have from a source that it was so much fun. If I ever come back I'll definitely schedule in a night out here! It's not too far from Wrigleyville which is also a fun place to have a boogie.

Firecakes Donuts
Oh Americans know how to do doughnuts right? These were incredible. So sugary and sickly sweet which is the only way a doughnut should be. Pick up a cup of their freshly squeezed orange juice too. I personally had a soft spot for the Old Fashioned Buttermilk and the Butterscotch Praline. Grab a couple to go and wander around the city enjoying the hustle and bustle.
Lou Mitchell's Diner
Lou Mitchell's is the starting point of the original Route 66 in Chicago. The portions are huge and the service is quick and to the point. It sets you up fantastically for the day! Have the scrambled eggs - they're so fluffy and dreamy. It's not the most fanciest of food but it's very good food. Nice comfort food which is always the ticket. They've been feeding the hungry mouths of road trippers since 1923 so there's lots of history steeped in the place.

Millennium Park
If the sun is shining, make sure you head to the park. Here you'll find the infamous 'Bean' aka Cloud Gate sculpture. You'll be able to see the beautiful skyline of the city reflected - take a walk underneath it. The park is a great place to wander around and gaze at the different sculptures, fountain and outdoor galleries. Grab a takeaway and sit down for a spot of people watching.
Odyssey Dinner Cruise
Lake Michigan is absolutely huge and the best way to appreciate it is with this dinner cruise. Setting off from Navy Pier, you'll be able to enjoy a three course dinner as the sun sets. It circles the river, offering you stunning views of the city behind you - I'm overusing the word stunning right? I just can't think of any other word! You'll get a free glass of champagne and a disco thrown in too for the price. Make sure you hop up to the observation desk for some great picture opportunities.


  1. Great guide lovely, Firecakes Donuts sounds lovely. Thank you for sharing. xx


  2. Adding all these to my list of places to go if I ever visit Chicago! The buttermilk and praline donut sounds right up my street too!

    - Elodie x

  3. These all look and sound incredible! xxx


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