Best known as the “Windy City” because the politicians blow hot air, Chicago is one of my favorite cities in the entire United States, especially in the summer when the weather is just perfect. The winter is harsh here and the city comes alive as resident buzz about after being confined inside for so long. There’s not one person I know who doesn’t say, “You can’t get better than Chicago in the summer.”
Chicago’s biggest draws include its green space, the most famous of which is Grant and Millennium Park, home to the famous Chicago Bean, as well as and architectural diversity. Definitely take an architecture tour of the city.
More than that, you’ll find world-class food, nightlife, lots of activities, outgoing people, and an uplifting atmosphere. There’s a lot to do here for people of any budget or travel style. I can’t rave about the city enough.
This travel guide to Chicago can help you plan an affordable and enjoyable trip here and will give you a list of all my favorite tips!
Table of Contents
Click Here for City Guides
Top 5 Things to See and Do in Chicago
1. Relax in Grant and Millennium Park
2. Visit the Art Institute of Chicago
3. Experience St. Patrick’s Day
4. Be a kid at Navy Pier
5. See Robie House
Other Things to See and Do in Chicago
1. Visit the Oriental Institute Museum
Despite its name, the collection has nothing to do with the Orient, but instead is a huge archaeological collection of objects from ancient Egypt. There’s even a giant statue of King Tut standing at 17 feet tall and weighing over six tons. The museum is open daily (except Mondays) from 10am-5pm, except on Wednesdays when it’s open until 8pm. Entry is $10.
2. See the Chicago Cultural Center
The former site of the Chicago Public Library, this lovely building is known for its exquisite Tiffany mosaics, especially in its performance venue, Preston Bradley Hall. Plus its rooms were inspired by the Acropolis of Athens, the Palazzo Ducale in Venice, and the Palazzo in Florence. It has changing art exhibits, and best of all, it’s free!
3. Stop by the City History Museum
This museum provides a good overview of the history of Chicago, especially of the Great Chicago Fire that burned down most of the city. Even President Lincoln’s deathbed is here! Admission is $19, and it’s open daily.
4. See the Cubs play
Locals are passionate about their baseball team! Get in the spirit and head out to a game, even if you don’t know a lot about baseball. It gets really intense when the Cubs play Chicago’s other team, the White Sox.
5. Eat the famous pizza
Chicago developed the deep dish pizza, as well as the stuffed crust pizza, and no trip is complete without trying at least one. The deep-dish pizza was invented by Pizzeria Uno, which is now a national restaurant chain. But, for something more local, Chicagoans swear by Lou Malnati’s. (I’m not a huge fan of deep dish but I was well impressed.)
6. Stroll down the Magnificent Mile
This stretch along Michigan Avenue is known for its upscale designer boutiques. Even if you don’t want to blow your budget on some expensive threads, it’s still an experience to stroll down the avenue and take in the sights, the people, and a look at the Chicago River.
7. View some war-inspired art
The National Vietnam Veterans Art Museum is a great yet seldom-visited museum. It features art that was created by Vietnam war veterans and, more recently, veterans from Iraq. It’s a stark reminder of our overly romanticized notion of war. Admission is free.
8. Get acquainted with nature
The Peggy Notebaert Nature Museum is a beautiful institution with roof-top gardens and plenty of information about the ecosystems surrounding Chicago. The “butterfly haven” is the most interesting — it’s an enclosed space with hundreds of butterflies, a waterfall, and garden paths. This museum is open daily, and it costs $9.
9. Meet a local
Chicago has a local greeter program, which offers free walking tours of various neighborhoods from a knowledgeable local. This is a great opportunity to see more of the city from a more intimate, ground-level perspective. I highly, highly, highly recommend doing this!! I love greeter programs!
10. Catch an improv show
Chicago is the birthplace of improv comedy, and a visit to the city wouldn’t be complete without catching a show. There are tons of companies here – many of which have given birth to comedy greats like Tina Fey, Amy Poehler, Stephen Colbert, Mike Myers, Steve Carell, Eugene Levy, Bill Murray, and a ton of others. Some of the most popular companies are Second City, Improv Olympic, and ComedySportz.
11. Go to the beach
When most people think of Lake Michigan, they don’t imagine sand, waves, and water as far as the eye can see — but it’s there! Downtown Chicago runs right next to the shore and offers a little piece of nature in a city of skyscrapers.
12. See the Willis Tower
The Willis Tower (formally called the Sears Tower) held the title of world’s tallest building for 25 years. Standing at 1,450 feet (110 storeys), visitors can take the elevator to the SkyDeck for panoramic views over Chicago. The SkyDeck’s Ledge is a glass box extending 4.3 feet over the city. Admission is $26.
13. Visit Shedd Aquarium
Shedd Aquarium is one of the most impressive aquariums in the country, known for its impressive architecture and its advanced approach to animal care and handling marine environments. There are 32,600 different species of sea life here. You can feed sharks, get to know some penguins, and even pretend to be an animal trainer for a day. It’s honestly one of the best aquariums I’ve ever visited! It’s $40 to visit.
14. The Field Museum of Natural History
This museum was built for the World’s Columbian Exposition of 1893, and to house its impressive biological and anthropological collections. Now the museum has 24 million objects, with everything from mummies, to gemstones, to dinosaur fossils. The museum is open from 9am-5pm every day, and admission is $40.
15. Stroll the Chicago Riverwalk
Do like the locals do and hang out on the south bank of the Chicago River, where you can walk the Chicago Riverwalk from Lake Shore Drive to Lake Street. Grab a glass of wine at the City Winery Chicago Riverwalk and enjoy some people watching.
16. Visit the Adler Planetarium
This is the first planetarium in the United States, with immersive theater programs, exhibitions, and other fun events (including lectures). You’ll get to virtually experience the depths of powerful black holes and the heights of Voyager 1, the farthest manmade object from earth. There are also awesome special events, like Adler After Dark. Admission starts from $19 and goes up from there depending on the exhibits you wanna see.
17. Take a food tour
Get to know the city through its culinary scene, from deep-dish pizza to microbreweries to Chinatown’s best restaurants. Chicago Food Tours (from Chicago Food Planet) offers a huge assortment of tours. Usually, they involve some educational element (for example, brunch with a side of architectural history). Tours start from $50.
Chicago Travel Costs
Hostel prices – During peak season, a bed in a four-six bed room will cost from about $40. For a room with eight beds or more, expect to pay around $36. During the off-season, a bed in a room with eight beds or more will cost from about $25 each night, while smaller rooms will cost about $30.
A basic private room with a shared bathroom for two costs from $100 per night during peak season. Prices are about $80 in the off-season.
Budget hotel prices – Nightly rates for a budget two-star hotel room start at about $100 in peak season. In the off-season, budget rooms start from $80.
There are lots of Airbnb options in Chicago. A shared room (like a bed in a dorm) averages about $37 per night, while a private room is about $52 per night. A full apartment averages about $114 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 $4, or a sandwich for $8. A full deep dish pizza starts from about $14 (share with someone!). A McMeal is about $8.
You can eat a mid-range restaurant for $15-20 per the main course, including vegetarian dishes. Dinner for one with an appetizer will cost you about $37, and another $5 for a beer.
Chicago has some really high-end restaurants if you’re looking to splurge. A whole prixe-fix menu could cost you up to $200! Otherwise, you can pay upwards of $40 for a plate of crab claws! Steaks start at $25, while soups and salads are from $14. A glass of red will cost about $11.
If you cook your own food, expect to pay $60 per week for groceries that will include pasta, vegetables, chicken, and other essential foods.
Backpacking Chicago Suggested Budgets
If you’re backpacking Chicago, expect to spend about $66 per day. This budget will cover a hostel dorm, public transportation, cheap local eats, some home cooked meals, and free attractions. If you want to see a few more attractions or drink more, add about $10 per day.
A mid-range budget of about $180 will cover staying in a hotel, eating out for all of your meals, all the paid attractions you want, and eating out at moderately priced restaurants for all your meals. (If you opt to stay in an Airbnb, you could save up to $50 per day since they are a lot cheaper than hotels.)
On a luxury budget of about $325 or more per day, you can do what you want! You can get a four-star hotel near the city center, any meal you want, drinks, and a few Uber rides.
If you come in the low season, you’ll pay about 25% less for accommodations.
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’ll spend more, some days you’ll 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 cities, there’s always pocked of affordability if you know where to look and what to do. 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 pass is $108 per person and gets you entrance into five different attractions like the Shedd Aquarium, the Skydeck, the Field Museum, 360 Chicago, and the Art Institute of Chicago.
- Redeem hotel points – Be sure to sign up for hotel credit cards before you go and use those points when you travel. This is especially helpful in big cities. Be aware that most hotels charge parking fees if you have a car, and adjust your budget accordingly.
- Couchsurf – Couchsurfing started in the United States, and free accommodation offered can make up for the lack of hostels. You’ll find plenty of hosts throughout the city who will show you around their town and let you stay for free.
- 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 teach you about the history of the eclectic neighborhoods or show you all the delicious food the city has to offer. Tours are offered daily but require advance reservations.
- Save money on rideshares – Uber, Via, and Lyft (my preferred company) 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. You can save money off your first rides with the following codes: Lyft (MATTHEW999 to save $10) and Uber (jlx6v to save $15).
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:
How to Get Around Chicago
Public Transportation – The Chicago Transit Authority operates the L Train (elevated subway train) and the bus system, and the website has a complete list of route planning tools. The L Train costs $2.50 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 Ventra ticket rather than a card, you’ll pay $3 per ride (the card itself costs $5, but that amount gets refunded when you register the card).
The train from the airport costs $5.
You can also take a city bus, which is $2.25 per ride deducted from your Ventra card, or you cay pay the driver $2.50 in exact change.
There are also passes available, including a one-day pass for $10, a 3-day pass for $20, or a 7-day pass for $28.
Water Taxis – Water taxis are really just a fun way to get around some parts of Chicago, including the Shoreline Water Taxi service, which takes people to various tourist attractions (like Shedd Aquarium and Navy Pier). Tickets are between $8-10. Chicago Water Taxi also offers shuttle services.
Bicycle – Chicago is incredibly bike-friendly, and Divvy is the name of the city’s bike-sharing program. There are 5,800 Divvy bikes in the city! You can get an unlimited day pass for $15 (for rides up to three hours each), or buy a single pass for $3 (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 and then $2.25 per mile. Each additional passenger costs $1 (and then 50 cents per each additional person after that).
Ride-Sharing – 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. You can save money off your first rides with the following codes: Lyft (MATTHEW999 to save $10) and Uber (jlx6v to save $15).
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 tourist crowds. Fall is especially nice, with daily temperatures averaging between 60-70°F (15-21°C). You’ll want to pack a sweater, but tourist attractions are less crowded, and hotel/hostel rooms are cheaper.
Summer (June to the end of 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 winter, unless you don’t mind some bitterly 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’ll 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, especially 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.
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.
- Momondo – This is my favorite flight search engine because they search such a wide variety of sites and airlines. I never book a flight without checking here first.
- Skyscanner – Skyscanner is another great flight search engline which searches a lot of different airlines, including many of the budget carriers that larger sites miss. While I always start with Momondo, I use this site too as a way to compare prices.
- 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! (If you’re new to Airbnb, get $35 off your first stay!)
- Hostelworld – This is the best hostel accommodation site out there, with the largest inventory, best search interface, and widest availability.
- Hotwire – This is probably the hotel site I use most. I really enjoy its blind booking process. They essentially say “we have a super rate on a 3-star hotel in Chicago’s City Center,” and you book it without knowing the hotel name. While that sounds scary, I’ve never ended up in a bad hotel and have saved a ton of money in the process. Highly recommended.
- Priceline – I like this website because it allows you to bid on hotels and save a lot more money than by booking directly. When used in conjunction with the bidding site Better Bidding, you can substantially lower the cost of your hotels — by as much as 60%. 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’ll get exclusive discounts when you click the link!
- STA Travel – A good company for those under 30 or for students, STA Travel offers discounted airfare as well as travel passes that help you save on attractions.
- 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.
- 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
In this section, I’ll give you my suggestion for the best travel backpack and tips on what to pack.
The Best Backpack for Chicago
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 more tips and tricks as well as suggested travel backpacks.
What to Pack for Chicago
- 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
- 6 T-shirts
- 1 long-sleeved T-shirt
- 1 pair of flip-flops
- 1 pair of sneakers
- 8 pairs of socks (I always end up losing half)
- 7 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
Small Medical Kit (safety is important!!!)
- Hydrocortisone cream
- Antibacterial cream
- Doctor-prescribed antibiotics
- Hand sanitizer (germs = sick = bad holiday)
- 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:
- 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
- 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:
Chicago Travel Guide: Suggested Reading
On the Road, by Jack Kerouac
Written in 1957, Jack Kerouac’s Beat Generation classic is a classic 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 his character, 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
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 belong. 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 really 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’s 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.
My Must Have Guides for Traveling to Chicago
This book shows you how to easily collect and redeem travel points so you can get free airfare and accommodation.
Kristin Addis writes our solo female travel column and her detailed guide gives specific advice and tips for women travelers.
This book features interviews with dozens of teachers and detailed information on how to land your dream job and make money overseas.
My best-selling book will teach how to master the art of travel so that you’ll save money and have a more local, richer travel experience.
Chicago Travel Guide: Related Articles
Want more info? Check out all the articles I’ve written on United States travel and continue planning your trip: