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Rooftop Bars, Live Music & Pizza in Chicago

A blonde woman in a black coat smiling in front of the backdrop of dark chicago skyscrapers

Updated on May 7th, 2024

For anyone who loves food, drink & live music then Chicago is the perfect place to be. I was lucky enough to have a friend in the city & based on local recommendations here are the best places to sample rooftop bars, live music & pizza in Chicago!”



Chicago, USA


The skyline, the mind-blowingly enormous lake, the live music & the pizza. I was lucky enough to have a local to show me around so felt it was only fair to share my favourite bits – rooftop bars, live music venues & the only 2 places apparently for a truly authentic Italian pizza! If you are interested in music then also check out my road trip of Nashville, Memphis & New Orleans


Bars with a view…
The stunning night view across the illuminated City from the Signature lounge, Chicago, USAThe Very High One: Signature Lounge

If you’re into being in the highest bar then at 1000ft this is the one for you. I inadvertently happened to be there on Valentine’s night which meant it was especially busy with couples wanting to be by the window & get their selfies. The bar is indoor but the views are spectacular!

Views from the skyscrapers of an illuminated City at night from London House, Chicago, USA

If you want the best table, my advice is to wait in the queue (if there is one) to go on the left-hand side where the views are (slightly) better & ask for a table at the window. If, like me, you like people watching then go further back and you can watch everyone jostling for positions.

There is a restaurant there too if you fancy a meal with your view, & ladies, don’t miss the toilets as the views are even better from here! Also, going to the bar means you get the same views as from the Skydeck on the 103rd floor but for the price of your drink rather than the US$19.50 entrance fee (you would miss the chance to walk on the glass-floored ledge jutting out over the side of the building though).

The view on a sunny day from London House, Chicago - For the St Patricks Day parade they turned the river green, USAThe One On The River: London House

It may not be the tallest but you have a choice of going indoors or outdoors with amazing views of the river, lake & Magnificent Mile. The building itself is beautiful so take a moment to have a look around the lobby area before heading up in the lift. The 21st floor is indoors with a restaurant attached but if you want rooftop you need to head to the 22nd floor. Don’t miss the opportunity to go a little higher into the cupola which gives a different perspective on the skyline while surrounded by the monument.

The One At Millennium Park: Cindy’s
The stunning night view across the illuminated City from Cindy's, Chicago, USA

Again, not the highest but with great views over Millennium Park, Art Institute & Lake Michigan. Cindy’s is located on the 14th Floor in the Chicago Athletic Hotel which has an interesting history & well worth a trip on the way up or down to the lobby. It used to be a private members club for the Olympians & the rich & although now a hotel, the lobby is all wooden-clad & obviously full of history. At Cindy’s, grab a drink & head to the terrace – it’s not big but it delivers the views.

Live music venues
For Non-Stop Blues: Kingston Mines

This is a great place to see live blues & never be disappointed. There is music 7 nights a week (closes at 4am) & it has 2 stages so as soon as one band finishes the audience moves to the other room & the next band starts up. Gritty but fun & a lively crowd.

Cover charge US$12-15

The view from backstage of the band playing at a Chicago blues clubFor Blues Heritage: Buddy Guy’s Legends

Not a pretty location but a great venue for live blues. There a lot of heritage from the owner Buddy Guy. He apparently plays several sessions each January (but you would need tickets for those!). When I went, the music started at 9.30pm, there was a small crowd but the band were great & got everyone dancing (including me which is no mean feat!).

Food is also served if you’re hungry but don’t expect any special culinary experience. Cover charge US$10 but apparently, US$20 for tickets on Fri & Sat and I would advise that you book ahead for bigger names.

Two Blues musicians, one on guitar and one on saxaphone on stage, Chicago blues clubFor Intimate Blues: B.L.U.E.S

My favourite & the most intimate of all the blues bars mentioned here. A smaller but excellent venue with a friendly crowd & great service. Closed on Mon & Tuesday nights.  Great view while waiting for the toilet as you are at the back, behind the stage.

Cover charge US$7 – 10

For Old School Jazz: Green Mill

A great venue for live jazz & feeling like you’ve gone back in time to the days of Al Capone (it was his favourite speakeasy apparently). You can sit in curved leather booths & when I was there we watched the band perform on a special stage behind the bar. The atmosphere was fantastic & the music amazing. I arrived at 11.45pm on Sunday, the place was heaving & still going strong when I left at 1.30am. Bring cash as the table service wouldn’t take cards for drinks.

Cover charge US$5

For Serious Jazz: Jazz Showcase

A historic venue & apparently the place to go to in Chicago to see the big names in jazz.  The room is amazing but if you’re not a jazz aficionado it’s worth checking out who & what kind of jazz they are playing. The night I went it was the most expensive cover charge of all the venues by a long way (US$30) but as I am not a jazz expert it was a little too progressive for me & the least enjoyable evening of all the venues. Tickets can be bought online or pay the cover charge on the door.

Cover charge between US$10 – US$35 (US$5 for students or musicians)

Authentic Pizza – The Italian Way!

You can’t go far in Chicago without finding a pizza restaurant but I have it on good authority that if you are looking for the true Italian taste & ingredients then there’s only 2 that will cut it. I ate in both & can highly recommend either. I eat a lot of pizza at home, usually a vegetarian version but for it to be really authentic, it’s all about the Margarita!

Forno Rosso Functional but very stylish & the pizza I can vouch for, it’s delicious. Instead of Margarita, I had the Bufalina with imported mozzarella & the only thing added was chilli oil. Highly recommended!

Spacca Napoli A bit more upmarket & apparently the best & most authentically Neapolitan pizza in Chicago. I can’t argue with that as the service was excellent & pizza & desserts delicious!

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  1. It’s been decades since I’ve been to Chicago, but I’d love to go back. I LOVE the idea of al fresco dining on a rooftop most anywhere. Thanks for sharing these great spots.

    1. Thank you, Nancy. I love the rooftop too. Hope you get back to enjoy Chicago’s at some time soon. Sue x

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