City Guide: Chicago, IL

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Chi-Town, The Second and Windy City, The Real Gotham.

Just a few affectionate nicknames that you will have heard or come to hear when in Chicago. A city which is most usually overlooked by many people (British in particular) as so many opt for the glitz and glamour of New York or LA instead. But I am here to tell you all the reasons why you should consider Chicago for your next city destination and break with the status quo.

First of all, you can get cheap return flights to here, like under £400 cheap if you are flexible with dates. We flew American Airlines – which, surprisingly – turned out to be one of the best flights to the US we have had in many years! We had heard lots of negative things about them but couldn’t fault them; no delays, new planes, attentive crew and direct from Manchester is only 8 hours. We normally fly Virgin, but with their latest ticket shake up and that they don’t fly non-stop, it was a bit of a non-brainer this time.  Another great place to check if you live in London is Norewgian, where you can get tickets from £124.90 each way!

The Bean

Shorts: Mango £29.99 (similar here), Knit Top: Forever 21 (old), Bag: J Crew  £128 (similar here), Shoes: £65 Birkenstock

The Sightseeing

For me, I had always wanted to see infamous Bean and Hancock Tower and they were the things I was most excited about. They didn’t disappoint, both equally impressive in their stature and surrounded by even more amazing architecture. Don’t be put off thinking that you will be with the masses seeing these, we went on 4th July weekend and yes it was busy, but the city is so wide everywhere you have a feeling of space everywhere you walk. Something which I appreciated more being 6 months pregnant whilst exploring.

A good tip – don’t queue with every other tourist at the Hancock for the 360 Observation deck, instead take the elevator to the Signature Room at the 95th and take in the views with a cocktail. Much more relaxing, space to roam and a comfy seat to spend as long as you want taking it all in. Best of all, it is free. 

Signature Room

I would highly recommend a river tour, we didn’t opt for the Architecture tours as a) they are expensive and b) too long, like 2 hours too long which is not pleasant in 34c heat I can assure you. So, we opted for the 45min Wendella River Experience at $20 which was excellent and covered all the major buildings you would want to see, plus they are in a handy location just off  Michigan avenue (Magnificent Mile) so one you have shopped, why not take a break on one of these and take in the sights.

My personal favourite of the trip was the Carbide & Carbon Building, a true 20’s architecture masterpiece and affectionally looks like a champagne bottle with its green and gold top. It is now home a Hotel but they have still retained many of the original feature throughout in the lobby, so it is worthwhile having a look in.

Must Sees:

  1. Hancock Tower
  2. The Bean
  3. Carbide & Carbon Building
  4. Magnificent Mile Shopping
  5. Boat Tour
  6. Maggie Daley Park
  7. Lakefront Trail
  8. Chicago Theatre
  9. Andy’s Jazz Club

The Neighbourhoods

One thing we make a point of when city breaking is to not stick to the downtown areas– ideally, a day max – because the best way to know a city is to explore where the locals hang too.

W Armitage Avenue

Summer House Santa Monica

For us, and our favourite, was Lincoln Park which runs from North/Clybourn station N Halstead Avenue to W Armitage Avenue and a nice loop back down N Clybourn Avenue. The route is a nice stroll with impressive houses, cafes, restaurants and indie boutiques; hallmarks of a well-to-do community, with young families and fitness aficionados.  We ate brunch at Summer House Santa Monica which was full to the brim (always a good sign) and the menu had such a great selection, not to mention the amazing bakery counter as you walk in to tempt you! Another great spot is Blue Door Farm Stand a few doors down and offers farm to table food and fresh pressed juices.

Logan SquareAnother great neighbourhood, and more of a contrast to Lincoln Park is Logan Square. It is much more spread out area, so the cafes and bars are more of a walking distance than a stroll. We got off at California and walked up N Milwaukee Avenue, past numerous brewers and roasteries, a cute shop called Steel Petal Press (they actually make cards and stationary in there!) until we reached Logan Square Park for a break. On the corner of the square is also the popular Lula Cafe which we didn’t eat in, but is renowned for their brunch in an eclectic space.

Park & Field

The highlight of Logan Square, and where we ended up sending a few hours at was Park & Field which had a great atmosphere. Part vintage sports bar, part family fun with outdoor games and most of all lots of Adirondacks to kick back in with a great craft beer menu, cocktails and food truck too. We ate dinner at 90 Miles Cuban Cafe and the food was incredible. So authentic, a lively dining experience and with the outdoor terraces you truly felt like you were in Cuba! We had the pleasure of traditional Flamenco whilst devouring Paella which was enormous and such good value at $30 for both of us.

90 Miles Cuban Cafe

Some other great food places worth mentioning are in the city, but are not your usual tourist fodder and really were great; especially for myself as I am Gluten & Dairy Intolerant. LouMalnati’s for deep dish pizza, it is in such a nice area in the Golden Triangle and all pizzas are made from scratch (so do expect to wait at least 30 minutes) don’t fall in to the trap of going to Girodano’s instead. Lastly, Wildberry Cafe for the best GF panackes, 5 fluffy pillows with lots of berries and syrup was my go to and it was so great we went twice! If you do decide to go for breakfast, be warned there is always a huge queue, but pop in and put your name and number down they will then text you when a table is ready (usually an hour- hour and half). Which if you visit the Randolph Street location means you have time to see the Bean and the Maggie Daley Park to work up an appetite!

Maggie Daley Park

Where To Stay

We stayed 4 nights in Chicago at the Sofitel Magnificent Mile and couldn’t recommend more. It was conveniently located a few mins from Michigan Avenue, on the doorstep of all the shopping you could want and no more than 15 mins walk to the river and parks. The rooms were immaculate and if like us you opt for a Luxury City Room you are guaranteed a skyscraper view, which for us was the Hancock Tower. Another great option is the St.Jane inside the beautiful Champagne building for a more boutique experience and located in the Downtown Loop.


Sofitel Chicago



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