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Chicago in style

IL 600x400 shutterstockAlison, our Assistant Product Manager loves city breaks and offers her view of a great alternative to NYC.

In the autumn I flew with United Airlines, via Newark Liberty, from Manchester to Chicago O’Hare. I flew Economy Plus on the transatlantic service - a B757 single aisle aircraft. United’s Economy Plus offers a 37” seat pitch, WiFi, power outlets, seatback on-demand entertainment system – these seats are at the front of the Economy cabin for easier boarding/disembarkation. 

After clearing immigration and customs at Newark, I headed for the ORD gate and was soon on board for the short hop to Chicago.

Taxis into the city cost about $40 and take about 45 minutes depending on the time of day. I was at the Fairmont Chicago Millennium by 6pm, and immediately headed out to tick off something from my ‘bucket list’!

The bar at the top of what was once called the John Hancock building, is 96 floors above the street and has spectacular views of the city and Lake Michigan. The Signature Lounge is the perfect place to see the sun set over the Midwest and watch the city come alive with lights – accompanied by a glass of wine or a cocktail. Drinks cost from $10 - $20, so it’s not the cheapest place to party, but worth it for the view.

Bucket list ticked, we stopped for pizza on the way back to the hotel – the city is famous for its deep-dish variety.

USA thumb Fairmont ChicagoBack at the Fairmont, I had time to soak in the atmosphere of this modern hotel, that’s full of stylish art. Although it’s very elegant, the staff couldn’t have been friendlier, something that’s typical of the Windy City’s residents.

Next morning we hit the town, Fairmont Chicago Millennium is only a block from the Chicago River, with its Riverwalk – I’m a film fan so loved being right where so many great movies and TV shows were filmed – think of Mercury Rising, Ferris Bueller's Day Off, The Blues Brothers, The Good Wife and Home Alone- there’s even a Chicago Film Tour.

The Magnificent Mile crosses the Chicago River here – and is a retail heaven as it’s Chicago's largest shopping district with various mid-range and high-end shops mixed with restaurants, museums and hotels.

After a day of sightseeing I was ready to dine in style and we headed to Shaw’s Crab House – a Chicago institution. Just off of the Magnificent Mile, at Shaw’s you can dine in 1940’s style, white table-clothed Dining Room, or enjoy a more casual affair in the Oyster Bar, and even if seafood is not your thing, they serve great steaks.

Day three was our sightseeing day. So we made the most of the superb breakfast buffet in the Millennium Room at the hotel before taking a morning coach tour that explored Chicago’s crime-related past in the Gold Coast, Lincoln Park, Old Town, the Loop areas of the city, and we heard little-known tales of legendary mobsters such as Al Capone.

After lunch we headed to Navy Pier, Chicago's number one tourist attraction with fifty acres of parks, gardens, shops, restaurants, family attractions and exhibitions. Here we joined the 75 minute Chicago Architecture River Cruise that pointed out some of the city’s most famous landmarks.

On our last day we squeezed in some morning shopping before heading out to O’Hare for our flight home. After our whirlwind trip I can definitely say Chicago – my kind of town!.


  • Art Institute of Chicago - more than 300,000 artworks, displayed in a sprawling complex of galleries and halls
  • Wrigley Field - home to the Chicago Cubs and perfect for a baseball game or a stadium tour (and for great concerts in the winter months)
  • The Second City – the comedy club that launched the careers of many distinguished comics such as Bill Murray, John Belushi, Joan Rivers and Steve Carell.

Did you know?

  • The world's first skyscraper was built in Chicago in 1885 (10 floors high) and until 1998 the Willis Tower (formerly the Sears Tower) was the tallest building in the world

Top tips:

  • Dress for the weather, especially in spring and autumn when the weather can change from summer to winter in a day!
  • Don’t miss the beach – summer visitors can enjoy Chicago’s 28 miles of beaches and parkland on the lakefront
  • Blues and beer – try Rosa's Lounge, Lagunitas Brewing Company or River Roast – great venues for authentic Chicago blues.

AliNeed help in creating the perfect Chicago trip?

Call our USA team on 0141 955 4000.

Happy holiday planning!

Alison, Assistant Product Manager USA


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