Chicago Travel Guide

Chicago Travel Costs

Hostel prices – During peak season, a bed in a 4-6-bed dorm costs about $40 USD. For a room with eight beds or more, expect to pay around $36 USD. During the off-season, a bed in a room with eight beds or more costs about $28 USD while smaller rooms start at $30 USD.

A basic private room with a shared bathroom starts at $100 USD during peak season. Prices drop to around about $75 USD in the off-season. Free Wi-Fi is standard and most hostels have self-catering facilities.

For those traveling with a tent, camping is available outside the city. A basic plot without electricity for two people starts at $18 USD.

Budget hotel prices – Budget two-star hotels start at $100 USD per night in peak season. In the off-season, prices drop to around $80 USD. Expect basic amenities like free Wi-Fi, AC, TV, and a coffee/tea maker.

There are also lots of Airbnb options in Chicago. A private room starts at $55 USD per night while an entire home/apartment averages $130 USD per night.

Food – Chicago has lots of fast food and street food options. You can get a huge hot dog, a chili dog, or a few tacos for under $5 USD, or a sandwich for under $10 USD. A full deep dish pizza starts from about $14 USD (Lou Malnati’s Pizzeria is the best place to order it). Fast food (think McDonald’s) is around $8 USD for a combo meal.

You can eat at an inexpensive casual restaurant with table service for around $16 USD for a main dish. For a three-course meal with a drink, expect to pay closer to $45 USD.

Chinese food is around $10-15 USD for a main dish and you can find Thai food for around $13 USD. Beer is $7 USD and a latte/cappuccino is $4 USD. Bottled water is $1.75 USD.

If you cook your own food, expect to pay around $60 USD per week for basic staples like pasta, rice, vegetables, and some meat.

Backpacking Chicago Suggested Budgets

If you’re backpacking Chicago, expect to spend about $75 USD per day. This budget covers a hostel dorm, public transportation, cooking your own food, and free attractions like walking tours, the parks, and the beaches. If you plan on drinking, add $10-20 USD to your daily budget.

A mid-range budget of about $220 USD includes staying in a private Airbnb or private hostel room, eating fast food and ethnic cuisine for most meals, enjoying a couple of drinks, taking the occasional taxi, and doing some paid activities like museum visits or a bike tour.

On a “luxury” budget of about $435 USD or more per day, you can stay in a hotel, eat out anywhere you want, drink as much as you’d like, take more taxis or rent a car, and do more paid activities. This is just the ground floor for luxury though. The sky is the limit!

You can use the chart below to get some idea of how much you need to budget daily, depending on your travel style. Keep in mind these are daily averages – some days you spend more, some days you spend less (you might spend less every day). We just want to give you a general idea of how to make your budget. Prices are in USD.

Chicago Travel Guide: Money-Saving Tips

Chicago is an expensive city, especially when it comes to attractions and accommodation. But, like any major city, there are always pockets of affordability if you know where to look. Here are some ways to save money in Chicago:

• Get the Chicago City Pass – This pass allows you to over 50% off admission at a number of attractions. A 5-Choice Explorer pass is $124 USD and gets you entrance into five different attractions like the Shedd Aquarium, the Skydeck, the Field Museum, and the Art Institute of Chicago. There are options ranging from 2-Choice to 7-Choice and also an all-inclusive pass.
• Redeem hotel points – Be sure to sign up for hotel credit cards before you go and use those points when you travel. Be aware that most hotels charge parking fees if you have a car, and adjust your budget accordingly.
• Couchsurf – Couchsurfing is the best way to save money in Chicago. You’ll not only get a free place to stay but you get to connect with a local who can share their insider tips. It’s perfect for budget travelers who want to make connections.
• Go on a free walking tour – This is a great way to learn the history behind the places you are seeing and to avoid missing any must-see stops. Free Chicago Walking Tours has several interesting walking tours that can show you the main sights. Just be sure to tip your guide!
• Save money on rideshares – Uber, Via, and Lyft are way cheaper than taxis and are the best way to get around a city if you don’t want to take a bus or pay for a taxi.
• Bring a water bottle – The tap water here is safe to drink so bring a reusable water bottle to save money and reduce your plastic use. LifeStraw is my go-to brand as their bottles have built in filters to ensure your water is always clean and safe.

Where to Stay in Chicago

Accommodations are expensive in Chicago. Before you book, make sure you have a hostel in the location where you want to spend most of your time. Here are my recommended places to stay in Chicago:

• Found Chicago River North
• Chicago Getaway Hostel
• Parthenon Hostel
• Hi Chicago, The J.ira & Nicki Harris Family Hostel
• Freehand Chicago

For more hostel suggestions be sure to check out my list of the best hostels in Chicago!

How to Get Around Chicago

Public Transportation – The Chicago Transit Authority operates the L Train (elevated subway train) and the bus system. Their website has a complete list of routes and planning tools. The L Train costs $2.50 USD per journey, which is automatically deducted from your Ventra card (a rechargeable card that you can buy at any L station). If you’re using a cash ticket rather than the Ventra card, it’s $3 USD per ride (the card itself costs $5 USD, but that amount gets refunded when you register the card).

The train from the airport costs $5 USD. You can also take a city bus, which is $2.25 USD with a Ventra card or $2.50 USD in exact change.

There are also passes available, including a one-day pass for $10 USD, a 3-day pass for $20 USD, and a 7-day pass for $28 USD.

Water Taxis – Water taxis are a fun way to get around some parts of Chicago. Tickets cost between $6-10 USD. Chicago Water Taxi also offers shuttle services.

Bicycle – Chicago is incredibly bike-friendly. Divvy is the city’s bike-sharing program. There are 5,800 Divvy bikes and you can get an unlimited day pass for $15 USD (for rides up to three hours each). You can also buy a single pass for $3.30 USD for a 30-minute ride. You can purchase these passes at station kiosks or via the app.

Taxis – Taxis are expensive here! Everything is meter-based starting at $3.25 USD and then $2.60 USD per mile. Skip the taxis if you can!

Ridesharing – Uber, Lyft, and Via are way cheaper than taxis and are the best way to get around a city if you don’t want to take a bus or pay for a taxi. The shared/pool option (where you share a ride with other people) offers even better savings. Via is the cheapest option.

Car rental – Car rentals can be found for as little as $35 USD for a multi-day rental. However, unless you’re leaving the city to do some day trips I would skip the rental as traffic is a pain and parking is expensive. Renters need to be at least 21 years old.

When to Go to Chicago

Spring (April to the end of May) and fall (September to the end of October) are both excellent times to visit Chicago, thanks to pleasant temperatures and fewer crowds.

Fall is especially nice, with daily temperatures averaging 60-70°F (15-21°C). You need to pack a sweater for this time of year, but tourist attractions are less crowded and hotel/hostel rooms are cheaper.

Summer (June-August) is peak season in Chicago. It’s hot, with temperatures reaching the mid-80s°F (high 20s°C), and tourist crowds are at their highest. Although it’s nice to take advantage of the weather, keep in mind that prices increase for accommodations and vacancies are low. August can be rainy, so pack a light rain jacket.

Avoid visiting in winter unless you don’t mind some super cold days! The wind can be sharp during the winter months in Chicago, but if you want to do a lot of museum hopping or sightseeing indoors, you can save a lot of money on accommodations.

How to Stay Safe in Chicago

Although Chicago gets a bad reputation for crime and violence, it’s still a safe place to backpack and travel. Violent attacks tend to be confined to certain areas (especially where drug and gang violence are a problem). As a visitor, you’re likely to stick to the Loop, Wicker Park, Bucktown, and the Old Town, which are all very safe.

Avoid Chicago’s South Side unless you want to see a White Sox game (the L Train stops right outside the stadium).

You might encounter petty crime, like theft, around famous tourist landmarks. Keep an eye on your belongings at all times, especially while taking public transportation. At some attractions, like the Art Institute or the Field Museum, you may get approached by scammers who claim they can give you a cheaper tour inside. Avoid these “guides” as it’s all a scam!

You can more about the 14 major travel scams to avoid when you travel.

if you experience an emergency, dial 911 for assistance.

Always trust your gut instinct. If a taxi driver seems shady, stop the cab and get out. If your hotel is seedier than you thought, move. Make copies of your personal documents, including your passport and ID.

If you don’t do it at home, don’t do it when you’re in Chicago. Follow that rule, and you’ll be fine.

The most important piece of advice I can offer is to purchase good travel insurance. Travel insurance will protect you against illness, injury, theft, and cancellations. It’s comprehensive protection in case anything goes wrong. I never go on a trip without it as I’ve had to use it many times in the past. You can use the widget below to find the policy right for you:

Chicago Travel Guide: The Best Booking Resources

Below are my favorite companies to use when I travel around Chicago. They are included here because they consistently turn up the best deals, offer world-class customer service and great value, and, overall, are better than their competitors.

• Skyscanner – Skyscanner is my favorite flight search engine. They search small websites and budget airlines that larger search sites tend to miss. They are hands down the number one place to start.
• Momondo – This is my other favorite flight search engine because they search such a wide variety of sites and airlines. I never book a flight without checking here too.
• Airbnb – Airbnb is a great accommodation alternative for connecting with homeowners who rent out their homes or apartments. The big cities have tons of listings!
• Hostelworld – This is the best hostel accommodation site out there, with the largest inventory, best search interface, and widest availability.
• Booking.com – The best all around booking site that constantly provides the cheapest and lowest rates. They have a no money down policy, great interface, and the widest selection of budget accommodation. In all my tests, they’ve always had the cheapest rates out of all the booking websites.
• Intrepid Travel – If you want to do a group tour around the United States, go with Intrepid Travel. They offer good small group tours that use local operators and leave a small environmental footprint. If you go on a tour with anyone, go with them. And, as a reader of this site, you get a discount when you click the link!
• EatWith – This website allows you to eat home-cooked meal with locals. Locals post listings for dinner parties and specialty meals that you can sign up for. There is a fee (everyone sets their own price) but this is a great way to do something different, pick a local’s brain, and make a new friend.
• Fat Tire Tours – Fat Tire Tours offers fun and insightful bike tours around the city. You get to see all the main sights with the help of a local guide and you can see the city in a whole new light. They’re a great alternative to your standard walking tour.
• World Nomads – I buy all my travel insurance from World Nomads. They have great customer service, competitive prices, and in-depth coverage. I’ve been using them since I started traveling in 2003. Don’t leave home without it!

Chicago Gear and Packing Guide

If you’re heading on the road and need some gear suggestions, here are my tips for the best travel backpack and for what to pack!

The Best Backpack for Travelers

What’s the best backpack for traveling long-term? I recommend the REI Flash 45 Pack. It’s light and comfy, front loading, and fits perfectly in an airplane’s overhead bin.
Size: 45-47L
Straps: Thick and cushy with compression technology that pulls the pack’s load up and inwards so it doesn’t feel as heavy.
Features: Removable top lid, large pocket at the front, hydration compatible, contoured hip belt

If you want something different, refer to my article on how to choose the best travel backpack for tips on picking a pack and other backpack suggestions.

What to Pack for Your Trip

Clothes

• 1 pair of jeans (heavy and not easily dried, but I like them; a good alternative is khaki pants)
• 1 pair of shorts
• 1 bathing suit
• 5 T-shirts (Unbound Merino is my preferred company. If you’re a member of NM+, you can get 15% off your purchase)
• 1 long-sleeved T-shirt
• 1 pair of flip-flops
• 1 pair of sneakers
• 6 pairs of socks (I always end up losing half)
• 5 pairs of boxer shorts (I’m not a briefs guy!)
• 1 toothbrush
• 1 tube of toothpaste
• 1 razor
• 1 package of dental floss
• 1 small bottle of shampoo
• 1 small bottle of shower gel
• 1 towel
• Deodorant

Small Medical Kit (safety is important!!!)

• Band-Aids
• Hydrocortisone cream
• Antibacterial cream
• Earplugs
• Tylenol
• Hand sanitizer (germs = sick = bad holiday)

Miscellaneous

• A key or combination lock (safety first)
• Zip-lock bags (keeps things from leaking or exploding)
• Plastic bags (great for laundry)
• Universal charger/adaptor (this applies to everyone)
• LifeStraw (A water bottle with a purifier)

Female Travel Packing List
I’m not a woman, so I don’t know what a woman wears, but Kristin Addis, our solo female travel guru, wrote this list as an addition to the basics above:

Clothing

• 1 swimsuit
• 1 sarong
• 1 pair of stretchy jeans (they wash and dry easily)
• 1 pair of leggings (if it’s cold, they can go under your jeans, otherwise with a dress or shirt)
• 2-3 long-sleeve tops
• 2-3 T-shirts
• 3-4 spaghetti tops
• 1 light cardigan

Toiletries

• 1 dry shampoo spray & talc powder (keeps long hair grease-free in between washes)
• 1 hairbrush
• Makeup you use
• Hair bands & hair clips
• Feminine hygiene products (you can opt to buy there too, but I prefer not to count on it, and most people have their preferred products)

For more on packing, check out these posts:

• What I Pack For My Travels
• The Ultimate List For Female Travelers
• How to Choose and Buy the Right Backpack

Chicago Travel Guide: Suggested Reading

On the Road, by Jack Kerouac
Written in 1957, Jack Kerouac’s Beat Generation classic is a must-read travel novel. Kerouac’s character’s (who he modeled after himself) frustration, desire to see the world, and adventures resonate with all of us who need a little relief from modern life. The story follows Sal as he leaves New York City and heads west, riding the rails, making friends, and partying the night away. He finds thrills, adventure, love, sex, drugs, poverty, and excitement while moving from a weak character into someone whose life experience brings confidence. It’s a true American classic.
 
 
Tip of the Iceberg, by Mark Adams
In 1899, Edward H. Harriman (a rich railroad magnate) converted a steamship into a luxury cruise for some of America’s best scientists and writers and embarked on a summer voyage around Alaska. Now, author Mark Adams retraces that expedition, traveling over 3,000 miles along the coast of the state. Mark is one of my favorite writers, and this book is very reminiscent of Turn Right at Machu Picchu. Mark brings insight into the people, history, and culture of the state in a way he did with his other book.
 
 
Wild, by Cheryl Strayed
Forgetting the hype of the book (and the subsequent movie), I really did like this book. Cheryl Strayed’s book is about her journey along the Pacific Crest Trail when she was 26. She sets off in hopes of finding herself and coming to grips with the death of her mother, break-up of her marriage, and drug use. She’s looking for a fresh start. Along the way, she encounters kindness, happy fellow hikers, and a deep sense of belonging. Filled with wonderful prose, I found this book deeply moving. It’s easy to see why the book became such a hit.
 
 
Dispatches from Pluto: Lost and Found in the Mississippi Delta, by Richard Grant
As a big fan of the state of Mississippi, I was keen to read this book. The state is an often-overlooked tourist destination with eccentric but wonderful people; beautiful parks, rivers, and swamps; stunning architecture; and a complex and rich history for history buffs like myself. In this book, English writer Richard Grant and his girlfriend move to rural Pluto, Mississippi, to live a better life, escape the big city, lower their cost of living, and try something new. They learn to hunt, garden, fend off wild animals, handle snakes, and befriend interesting characters along the way.
 
 
The Not-Quite States of America, by Doug Mack
The United States of America is more than just 50 states. There are also the non-states of American Samoa, Guam, the Northern Mariana Islands, Puerto Rico, and the US Virgin Islands. In this funny, detailed, fact-rich book, Doug Mack explores these territories largely forgotten by the rest of the country, which play a more important role in our country than we realize. I had the pleasure of listening to Doug talk about his book in NYC, and he’s a wealth of knowledge — just like his book! This one of those travel books that expands your mind about the place you don’t really know.
 
 
Blue Highways: A Journey into America, by William Least Heat-Moon
This is a deep dive into America’s unknown tiny towns scattered across the country map, like New Hope (Tennessee), Remote (Oregon), Why (Arizona), and Whynot (Mississippi). Yes, those are real town names! Heat-Moon’s book is considered a masterpiece in American travel writing and you’ll love his adventures and the incredible people he encounters as he reveals the “real” American experience.