Historic Route 66 Sign
Head to East Adams Street, just off South Michigan Avenue in Downtown Chicago and look up. Youll find a surprising historic monument there which will make a great photo for your Instagram account. Snap a shot with the historic Route 66 sign to get your own personal memento of the iconic highway.
Route 66 is probably the most well-known highway in the world and has been immortalized in films, songs and stories. The original road was almost four thousand miles long and stretched from Chicago right the way across the US to Santa Monica in California. It begins, and ends, in the Loop.
West Loop / West Town Best Chicago Neighborhood For Foddies
Chicagos former industrial district, the West Loop has since become one of the citys trendiest and most diverse boroughs. Since the turn of the 20th century immigrants have defined West Towns culture, with their influence continuing to be celebrated through the many sights, sounds, and tastes of the area.
Arguably Chicagos dining hotspot thanks to its Restaurant Row, the West Loop boasts an unending assortment of dishes and food items from around the world, with more than its share of pubs and live music venues to satiate any nightlife champion.
The French Market, located just inside the Ogilvie train station, spotlights such fare as Belgian fries, lobster rolls, Hawaiian poke bowls, and all manner of pastries and produce, making it the perfect destination for high-end strolling and sampling.
Its not just food thats a major draw in the West Loop, however the Arcade Emporium at Fulton Market is a gamers paradise with its pool and air hockey tables, pinball machines, and arcade games, while Brooklyn Boulders gives you the opportunity to rock climb indoors.
For an especially Big Lebowski-worthy evening, you can head to Punch Bowl Social for bowling and brews.
BEST PLACES TO STAY IN WEST LOOP
Recommended Area: Chicago Loop
Chicago Loop is considered the financial and commercial district of the city, with large office buildings and stores on State Street that make it a very attractive area for shopping enthusiasts.
It is in this area that you will find Millenium Park, the main vegetable lung of the city, as well as the Theater District, ideal to enjoy the most recent plays of Chicago and get caught up in the culture of this great city.
Similarly, this district has a large number of museums, such as the Art Institute of Chicago, the Cultural Center of Chicago, the Museum of Contemporary Photography and the Museum of American Writers.
Chicago Loop has the best public transport connections in the city, with elevated rail stations such as Quincy, Monroe, and Jackson, to name just a few.
Furthermore, Chicago Loop is one of the best areas to stay in Chicago because of its variety of hotels of all types.
Why is this a recommended area to stay in Chicago, Illinois:
- Central location
- Best area to stay without a car
- Best area for sightseeing
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Best Hotel In Downtown/the Loop: Central Loop Hotel
The Central Loop Hotel has stylish décor, spacious rooms and is centrally located in Downtown Chicago. It has a modern lounge bar, concierge service and a convenient 24-hour reception. Each room is air-conditioned and comes with coffee/tea facilities and on-demand movies. All of this combined makes it our choice for where to stay in Chicago in the Downtown area.
Talbott Hotel A Popular Trendy Boutique Hotel On The Magnificent Mile
Just a few short steps away from the iconic Magnificent Mile on Michigan Avenue, the 4-star exceptionally rated Talbott Hotel offers well-appointed rooms and effortless style throughout. Opulent interiors marry retro chic with industrial touches, whilst the elegant rooms at this cool and unusual Chicago stay are well thought out and full of modern conveniences including free Wifi, widescreen TVs as well as Italian linens.
Upgraded rooms come with Apple Mac Mini computers and soaking tubs. Enjoy a drink or two in the contemporary chic hotel restaurant, 20 East, offering a thoroughly modern take on traditional American fare and a wide selection of craft beers. You can always work off those extra calories in the onsite fitness center. Also dont miss the chance to eat alfresco on the streets of Chicago in the hotels beautiful patio area! Sublime!
- Prices from $120 per night.
- To book, check prices or availability for The Talbott Hotel
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When To Visit Chicago
Unless you enjoy painfully cold weather with stinging winds, its best to skip out on winter in Chicago. Sure, you can find plenty of fun things to do indoors, but many parts of the city arent that enjoyable in winter.
Summer in Chitown is a very exciting time with lots of events going on like Lollapalooza and Taste of Chicago. That being said, it can be more crowded and expensive on these popular weekends.
Alternatively, both spring and fall are excellent choices if you want to experience the best of the Windy City. Then you can enjoy it in pleasant weather without the crowds.
Best Airbnb In Downtown/the Loop: Bright And Stylish Loft
When visiting a city for the first time, you should base yourself right in the heart of the busy streets. This cool loft is the perfect spot for a couple or solo travellers that want to explore Chicago as much as possible. Youll be in walking distance to public transport options and close to many of the cities best attractions. If you dont feel like going out during the day, just enjoy your stylish home its super welcoming, theres a TV and a fully equipped kitchen, and you can even use the buildings gym if you want.
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Chicago Loop Best Chicago Neighborhood For Business Travelers
Its called The Loop because the CTA, or Chicagos public transportation system, makes a loop around the downtown area. I consider it to be anything south of the River and north of Roosevelt, from the West Branch of the River to the Lake. This is largely the Central Business District of Chicago and as such, can be a bit quieter in the evenings and weekends. However, the eastern part of the Loop is also Chicagos theater district, so there is a bit of nightlife and a few hotels near Chicago Theater that are worth exploring. Hotel prices in the Chicago Loop can vary greatly based on conventions and events. Its possible to snag some great weekend deals, as most hotels cater to business travelers.
Some of the main attractions in the Chicago Loop include Willis Tower Buckingham Fountain, Daley Plaza, Christkindl Market, Millennium Park, Grant Park, State Street shopping, and the Art Institute of Chicago, along with some of the best architecture in Chicago. If you are arriving in Chicago by train, Union Station and Ogilvy Station are both in the loop, and Ogilvy has the French Market with some of the best donuts in Chicago. During the week, some of the best Chicago food trucks can be found near Willis Tower. This is definitely one of the best places to stay in Chicago!
The Kimpton Gray Hotel A Beautiful Upscale Boutique Hotel With An Art Deco Design
Set in one of Chicagos finest landmarks, the 4-star very highly rated Kimpton Greyis the height of opulence, offering smart, sophisticated, and stylish Art Deco-inspired accommodation throughout. The ornate high-rise building dates from 1894 and the trendsetting Chicago hotel is just is a 12-minute walk from central Millennium Park and offers some of the finest views you can find in the city.
With quirky amenities on offer like loaner bikes, nightly wine socials, and a yoga mat in every room, you will be staying in a cleverly crafted luxury environment. The rooftop lounge serves light bites and refreshments, and the day spa, salon, and fitness centers offer all the complimentary facilities you would expect from such an upmarket hotel. Just an all-round beautiful place to stay in Chicago.
- Prices from $100 per night.
- To book, check prices or availability for Kimpton Grey Chicago
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Then Theres The Free Stuff
I thought Id won the jackpot with the spacious room, but that wasnt all . One of the key features of Embassy Suites is their Cooked-to-Order Breakfast. A generous-sized buffet with meats, cheese, pastries, potatoes, pancakes, waffles and more met us each morning. Plus a chef cooked on-request omelettes, scrambles eggs and my favourite fried eggs.
Our chef was a comedian and gave me a laugh. I love a chef with attitude! But importantly, he knew how to turn around dishes fast. In fact, he looked like a videotape running at double-speed.
Ok, so breakfast is great. But why is everyone returning to the hotel between 5:30pm and 7:30pm? TheManagers Reception. Every night you can find light snacks and FREE alcoholic and non-alcoholic drinks. Yep, you read that right.
We attempted to be back every evening for our free cocktail after a full day of sightseeing. I was floored. Usually cocktail hour is reserved for exclusive club lounges. But here its for everyone.
Old Town Nice Area Where To Stay In Chicago
Settled by German immigrants in 1850, Old Town feels like stepping back in time. With its beautiful Victorian architecture, quiet tree-lined streets, and lively goings-on, Old Town frequently ranks high among must-see areas during a stay in Chicago.
The famous Second City Theater, where such comedic legends as John Belushi, Tina Fey, and Stephen Colbert got their start, is a landmark attraction while the edgier Zanies, whose alumni includes the likes of Aziz Anzari, offers adults-only humor.
Just around the corner from Second City is the Old Town Pour House, which on any given day offers at least 90 beers on tap, while the areas surrounding shops and eateries leave nothing to be desired on the food aficionado front.
BEST PLACES TO STAY IN CHICAGO IN OLD TOWN
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What Are The Best Hotels In Chicago
The ones on this list, of course. As a self-proclaimed ambassador for Chicago who’s always encouraging friends to visit, I’m always asked for recommendations on where to stay. My answers typically depend on the person’s style preferences, location requirements, reasons for visiting, and of course, budget. These factors similarly fueled this very list, to highlight the hotels that best tick all those boxes: stylish, centrally located, near business and leisure, and are reasonably priced.
Best Airbnb In Chicago: Bright And Stylish Loft
When visiting a city for the first time, you should base yourself right in the heart of the busy streets. This cool loft is the perfect spot for a couple or solo travellers that want to explore Chicago as much as possible. Youll be in walking distance to public transport options and close to many of the cities best attractions. If you dont feel like going out during the day, just enjoy your stylish home its super welcoming, theres a TV and a fully equipped kitchen, and you can even use the buildings gym if you want.
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Recap Of The Best Places To Stay In Chicago
That about wraps it up for this guide on the best places to stay in Chicago. Whether you choose to base yourself downtown in the Loop, along the Magnificent Mile, or up in Lincoln Park, youre sure to have a great time exploring the Windy City.
Theres so much going on in Chicago that youll likely be planning a return visit before you leave. Go ahead and check out a different neighborhood next time so you can experience different sides of the city.
Ive been going to Chicago for nearly 30 years now and always discover something different when I go. Its one of my favorite cities in the country, and I hope you end up falling in love with it as well!
This is a post written by contributor, Sasha. He is a teacher, writer, and video producer from Detroit, Michigan. He graduated from Michigan State and has since lived in China, Indonesia, Mexico, and Colombia. Sasha and his wife Rachel run Grateful Gypsies, where they write about teaching ESL, digital nomad life, long-term travel, live music, and more.
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Thewit A Doubletree By Hilton
Accommodations: Described as trendy and glamorous, theWit has rooms with 2 Queen beds that can accommodate a family of five , but only if one child is a baby or toddler. A crib, but not a roll-away, can be requested in this room type. However, the hotel has connecting rooms available for larger families. Hotel
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The Guesthouse Hotel A Chic Apartment Hotel And An Awesome Place To Stay In Chicago
The Guesthouse Hotelpens itself as a luxury home away from home, offering affordable, comfortable accommodation in the Lincoln Park neighborhood of the city. Stop outside this highly rated hip Chicago hotel and you can explore the upscale stores on central Armitage Avenue, or the cafés, restaurants, and sweet shops of Clark Street and the historic
Andersonville neighborhood. The Guesthouse offers one, two and three bedrooms suites that easily offer the same size accommodation as many city apartments do, and are all beautifully appointed throughout with granite kitchens, private balconies or patios with gas grills and some have soaking tubs.
With chic, modern contemporary decor, and long stays available, The Guesthouse really does offer visitors to the city the perfect crash pad no matter how long they intend to stay. Opt for a penthouse suite if you can as they come with a private rooftop deck offering truly gorgeous skyline views!
- Prices from $140 per night.
- To book, check prices or availability for The Guesthouse Hotel
Blackstone Hotel images are copyright of Blackstone hotel. The first image for the Talbott Hotel was taken by ThelightingJudge.com
The Gwen A Luxury Collection Hotel
Best for: Couples, business travelers
On-site amenities: Rooftop terrace, restaurant, events and programming including tea time and movie nights.
Pros: The trendy rooftop terrace is a highlight of staying here, as is the location on Michigan Avenue. Head right into the adjacent mall without stepping foot outside.
Cons: Being right on busy Michigan Avenue can also mean it’s not the quietest spot. Some guests complain of blaring horns and street noise.
Located right on iconic Michigan Avenue, The Gwen, a Luxury Collection Hotel from Marriott Bonvoy, is set in a 1920s Art Deco landmark building .
Bright and modern rooms come with ultra-luxe Frette linens and a plush bed. Amenities include excellent on-site restaurants from one of Chicago’s most celebrated chefs and the sleek rooftop terrace has fire pits and a unique “curling” rink in winter.
COVID-19 procedures are available here.
Best for: Couples, groups of friends, families
On-site amenities: Restaurant, rooftop lounge, fitness center, pool
Pros: Many rooms have great city views including a sliver of the lake in the distance. Don’t miss a chance to eat at Somerset, the excellent on-site restaurant.
Cons: While some rooms boast lake views for an added cost, they may not be full-on views. Also, there’s no on-site spa, which is surprising for a luxury-leaning hotel of this caliber.
From the beautifully restored 1930s façade to the 30-foot lobby wall of quotes, the Viceroy is all about looks.
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