Best known as the “Windy City” because the local politicians blow hot air, Chicago is one of my favorite cities in the entire United States — especially in the summer when the weather is perfect.
Because the winter is harsh here, the city comes alive in the spring and summer as residents buzz about after being confined inside. 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 being Grant and Millennium Park, home to the iconic Chicago Bean. The city also boasts world-class food, a fun 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 a fun and affordable trip without breaking the bank!
Table of Contents
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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. Have fun at Navy Pier
5. See Robie House
Other Things to See and Do in Chicago
1. Visit the Oriental Institute Museum
Despite its name, this collection has nothing to do with “the Orient” but instead is a huge archaeological collection of objects from ancient Egypt. Established in 1919, the museum has all kinds of artifacts, photographs, historical records, and even a giant 17-foot-tall statue of King Tut that weighs over six tons! Suggested admission is $10 USD.
2. See the Chicago Cultural Center
The former site of the Chicago Public Library, this historic landmark is known for its exquisite Tiffany mosaics, especially in its performance venue Preston Bradley Hall. Its rooms were inspired by the Acropolis of Athens, the Palazzo Ducale in Venice, and the Palazzo in Florence. It has changing art exhibits, events, and performances. Check the website to see what events and performances are available during your visit. It’s free too!
3. 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 while learning about it directly from an expert local guide who can answer all your questions. You can sign up chicagogreeter.com (you need to do it at least 10 days in advance). I highly, highly, highly recommend doing this!!
4. Stop by the City History Museum
This museum provides a solid overview of the history of Chicago, with an in-depth focus on the Great Chicago Fire in 1871 that burned down most of the city (the fire killed 300 people and left 100,000 people homeless. Abraham Lincoln’s final draft of the Emancipation Proclamation was lost in the fire too). The museum has 22 million items, including President Lincoln’s deathbed and the clothing he and his wife wore when he was assassinated. Admission is $19 USD.
5. See the Cubs play
Locals are incredibly 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’s still super fun. It gets really intense when the Cubs play Chicago’s other team, the White Sox. The season goes from March-November and tickets usually cost around $30 USD, though you can often find them for half that price.
6. Try deep dish pizza
Chicago developed the deep-dish pizza, as well as the stuffed crust pizza, and no trip is complete without trying both. 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. Personally, I’m not usually a huge fan of deep dish but I was impressed!
7. 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 enjoy the view of the Chicago River.
8. 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 offers a huge assortment of tours depending on your culinary interests. Usually, they involve some educational element (for example, brunch with a side of architectural history). Tours start from $65 USD.
9. View some war-inspired art
The National Veterans Art Museum (formerly The National Vietnam Veterans Art Museum) is a great yet seldom-visited museum. It features over 2,500 works of art created by Vietnam war veterans and, more recently, veterans from Iraq and Afghanistan. The entrance has 58,226 dog tags hanging from the ceiling, representing the soldiers who died in Vietnam. It’s a stark, somber reminder of our overly-romanticized notion of war. Admission is free.
10. Get acquainted with nature
Established in 1857, 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 over 200 species of butterflies, a waterfall, and garden paths. They also organize dozens of educational programs for both kids and adults. This museum is open daily and it costs $9 USD.
11. 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. Second City is the most popular venue/troupe. Expect to pay around $40 USD for a show.
12. 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. North Avenue Beach, 57th street Beach, Montrose Beach, and Ohio Street Beach are some of the best and most popular choices.
13. See the Willis Tower
The Willis Tower (formally the Sears Tower) held the title of the world’s tallest building for 25 years. Currently, it’s the third-tallest building in the US and the 23rd tallest in the world. Standing at 1,450 feet (110 stories) tall, visitors can take the elevator to the SkyDeck for panoramic views over Chicago. For those who don’t mind heights, the SkyDeck’s Ledge is a glass box extending 4.3 feet over the city, offering heart-pounding views of the urban landscape below. Admission is $35 USD.
14. Visit the Shedd Aquarium
Shedd Aquarium is one of the most impressive aquariums in the country, known for its impressive architecture and its ethical approach to animal care. 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 USD to visit.
15. Explore the Field Museum of Natural History
This museum was built for the World’s Columbian Exposition of 1893 to house its impressive biological and anthropological collections. Built in the Neoclassical style, the museum has 24 million objects, including exhibits on mummies, gemstones, meteorites, dinosaur fossils, and more. There’s also a library with over 275,000 books. Admission is $40 USD.
16. 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. It’s a gorgeous place for a stroll in the summer!
17. Visit the Adler Planetarium
This was the first planetarium in the United States. It boasts immersive theater programs, rotating exhibitions, and other fun events (including lectures). You can 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 which lets you explore the planetarium while enjoying drinks and live entertainment. Admission starts at $19 USD.
18. Take a bike tour
To explore the city’s main sights and cover a lot of ground, take a bike tour. Fat Tire Tours uses expert local guides so you learn a ton about the city. It’s a fun way to explore and you get to see a lot too!
For more information on other cities in the United States, check out these guides:
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
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
- 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
Small Medical Kit (safety is important!!!)
- Hydrocortisone cream
- Antibacterial cream
- 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 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.
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: