Skip to Content





This Chicago Travel Guide shares everything you need to know before visiting the city, including where to stay, what to do and how to save.

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 America’s 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.

10 things you have to do in chicago

Typical costs in Chicago


Budget: 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: $120 -$200 for private but spacious rooms in good locations. The Chicago Loop is one of the best places to stay in Chicago, with plenty of midrange options but book in advance as these book quickly in the summer months. 

Luxury: $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.

The 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.

Best time to visit Chicago

Chicago in Spring and Autumn is the best time visit, when the weather is cool but room rates are still low. 

Visiting Chicago in the Winter can be magical, especially if you visit over the Christmas period. However, the weather it bitterly cold so it is best to avoid visiting from October through to May unless you are looking for a festive experience or travelling on a budget. 

Chicago is home to many different festivals, which run throughout the summer too. 

Where to stay in Chicago


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.


HI Chicago Hostel offers rooms from $133 USD in the center of Chicago in the South Loop area.

Raffaello Hotel is a 4-star hotel costing $174 USD that can be found among the busy skyline of Chicago; standing alongside the John Hancock Center

Top End:

Royal Sonesta 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 advance – only really worth it if it’s at a cheaper rate.

Save money in Chicago

America is not the best place to start if you are travelling on a budget but there are many ways you save money travelling the USA. 

  • Chain hotels – The USA has many budget chain hotels. These are basic and make sure to check reviews on Yelp and Tripadvisor first, but you can save some serious money staying in places like Econolodge, Travelodge, Days in and Super 8. 
  • Hotels with kitchenettes – When booking a hotel or motel, check if there is a kitchenette. If there is a room or hotel with a kitchenette, then opt for that choice, especially if you are staying somewhere for an extended period of time. This means you can save loads of money cooking food yourself rather than eating out. 
  • Farmer markets – Heading to farmer markets or ethnic grocery stores can save you money on snacks and food.
  • Early Bird – When eating out, either aim to have a big lunch or head to a restaurant before 5. Many places offer an early bird option, where you can save money when eating between 2 – 5pm. 
  • Coupons – Pick up the local newspaper to find coupons for attractions and restaurants each week. If you plan on visiting a chain restaurant or cafe (such as Starbucks), check for vouchers or gift certificates on Ebay. 
  • Reward cards – If you travel a lot, why not get a rewards credit card for your favourite hotel chain. Hilton and Marriott have a great sign-up offers, so you can collect points each time you spend money on the card and then redeem free stays and upgrades worldwide. 
  • Compare rentals – If you intend on road tripping, make sure you compare prices for a rental car on websites such as or 
  • Turo – Another option if you are looking to rent a car is by using or This is a similar concept to Airbnb but for cars; you can rent a car from owners and this can work out cheaper than renting from a rental company. 
  • Avoid checked luggage – If you are flying in or out and visiting for a short period, avoid having checked luggage. You can book budget flights to save money but these don’t always include checked luggage. 
  • Hotel Tonight – This app can be used in big cities such as New York, LA, Chicago, Miami and Vegas. It offers last-minute rooms, particularly great if you are thinking of a weekend away. 
  • Download a Wifi Map  – This map is fantastic at finding available Wifi Spots in your area. These aren’t just Free Wifi Spots too, they have a database of passwords to make your connection reliable and safe. 
  • Avoid Public Holidays – Hotel and travel prices rise around the 4th July and Labor Day, so avoid travelling at this time. If you do want to travel at this time, book everything in advance. 
  • Avoid hostels – Hostels are a great way to save money on accommodation everywhere else in the world but not in the US. There aren’t many hostels and most are overpriced. If you are travelling by yourself, you are better off using a budget hotel or look for a bedroom on Airbnb. 
  • Free attractions – Chicago is full of attractions that cost nothing, so head to the parks and Navy Pier for a cheap day. 
  • Chicago City Pass – This city pass saves you money on the major attractions if you plan on seeing a lot during your time in the city. 
  • Use Ticketmaster – We loved watching the Chicago Cubs but it was expensive to get tickets last minute. Save money by booking tickets in advance on Ticketmaster. 

Best things to do in Chicago

  • Willis Tower Skydeck
  • Grant Park & Buckingham Fountain
  • Millennium Park & the bean
  • Wrigley Field & the Chicago Cubs
  • Navy Pier
  • Chicago River Cruise
  • Deep Dish Pizza
  • Art Institute of Chicago
  • Al’s Beef
  • Riverwalk
  • John Hancock Center
  • Chicago Cultural Center
  • Maggie Daley Park
  • Buckingham Fountain
  • Museum of Science and Industry
  • Time Out Market Chicago
  • Garfield Park Conservatory
  • Lincoln Park Zoo
Chicago Travel Guide

How to get to Chicago

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. One other such option is Chicago Bus Charter: if you’re planning a group, party or family vacation to soak in the Chicago Cultural scenery, their convenient amenities, properly chauffeured airport transfers and 24-hour support can make the difference. 

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 disappointment.

How to get around Chicago

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.

This site uses Akismet to reduce spam. Learn how your comment data is processed.