Chicago; ‘the windy city’, will blow you through parks, skyscrapers and top-notch restaurants. A relaxed city with some beautiful architecture and stunning parks, Chicago is a great place to spend a few nights and the starting city of Route 66.
The city for Artists, Chicago is known for its performing arts centre, Art Institute and fabulous sculptures and architecture found in Grant and Millennium Park. Check out the Cubs play at Americas oldest standing baseball stadium and check out one of the great music festivals held throughout the year. There are many things to see and do in Chicago.
Hostel/Budget rates – Similar to the rest of the States, accommodation is pricey. Dorm beds are found at $29 – $50 whilst private rooms can be found $60 – $100.
Midrange Hotel rates – $120 -$200 for private but spacious rooms in good locations.
Luxury Hotel rates – $210+ for the top luxury choices.
Transport – Bike Rentals cost $7 for 24 hours, the water taxi costs $8 for an all day pass, a standard bus fare is $2.25, unlimited ride passes on the subway train is $10 a day or $28 for a week pass, whilst individual tickets cost $3.
Average cost of food – Cheap eats like burgers, pizza and hot dogs can be found for around $5 with some fantastic deli and sandwich spots costing between $4 -$9. You can expect to pay between $15 – $30 per person at a sit down restaurant.
Where to stay
Hostel/Budget – Freehand Chicago can be found in Chicago’s vibrant river north area, with dorms starting at $45 and private rooms at $85. IHSP Chicago Hostel is another popular spot with private rooms starting at $61 with shared bathrooms.
Midrange – HI Chicago Hostel offers rooms from $133 USD in the centre of Chicago in the South Loop area. Raffaello Hotel is a 4 star hotel costing $174 USD that can be find among the busy skyline of Chicago; standing alongside the John Hancock Center.
Top End – The Wyndham Grand Chicago Riverfront Hotel is just a 5 minute walk from Millennium Park, offering luxurious and spacious rooms from $209. The Inn of Chicago Magnificent Mile is a fairly nice hotel, we stayed here during our last visit as we managed to get it on a good deal. Rooms start at $245 a night but you can get the room cheaper if booked in advanced – only really worth it if it’s at a cheaper rate.
How to get there
Fly – Most visitors arrive by air, arriving at O’Hare International Airport or Chicago Midway Airport. From O’Hare International you can catch the CTA blue line which runs to the Loop, taking about 40 minutes and costing $5, from here you can walk or hail a taxi. From Chicago Midway Airport you can catch the CTA orange line which also runs to the Loop, taking about 30 minutes and costing $3.
Bus – Megabus offers buses to and from major Midwestern cities at cheaper prices than Greyhound. Buses arrive and depart near Union Station on Canal St and tickets must be purchased in advance online. Greyhound offers bus journeys nationwide, with its main station near the CTA blue line Clinton stop.
Train – Amtrak connects Chicago to Milwaukee, St Louis and Detroit, with one daily train running to NYC and San Francisco.
Drive – Many either start or end their route 66 drive from Chicago, with car rentals available from O’Hara Airport. It is advised you arrange car rentals in advance to avoid queuing or disappointed.
Divvy, Chicago’s bike-sharing program, allows you to check out a bike for $7 for 24 hours. The first 30 minutes are free and rates rise after that, but if you get your bike back into a station around the city within those 30 minutes you aren’t charged etc. One of the most enjoyable ways to discover Chicago is on the river; with the Chicago water taxi costing $8 for an all day pass. CTA buses follow major roads throughout the day whilst the Medway (underground walkways) is the best choice for walking around Chicago during the Winter months. Flash cab, Yellow Cab and Hailo are reliable taxi companies in the area; with fares starting at $3.25 and costing $1.80 for every additional mile. CTA operates an elevated subway train system, getting you to most sights, hotels and districts in Chicago. The network is colour coded with 8 lines and a Ventra card is available from $3 whilst unlimited ride passes cost $10 a day.