I get asked a lot, what is there to do in Chicago? So instead of providing a boring answer, I decided to create a comprehensive free Weekend in Chicago guide. I live in Chicago and there is plenty to do that isn’t your typical touristy things.
This weekend travel guide is for tourists traveling for around a 3-5 days in Chicago. This guide is meant to give essential information, obvious sights, how to travel like a local and how I would spend a weekend in Chicago. This guide is designed to maximize time and money spent for people who are spending only a short time traveling here.
Most travelers will arrive in Chicago by plane and land at either O’Hare or Midway.
It is the bigger airport and is located on the extreme northwestern part of Chicago. Serviced by most major US Airlines and international airlines.
The Blue Line ‘L’ – The Blue Line runs from O’Hare to the Loop for $2.25 one-way ticket and operates 24/7. From downtown it’s possible to take a short cab ride to your hotel or transfer with one of the many bus routes.
Taxi from O’Hare – It costs around $45 – $60 from O’Hare to Michigan Ave and the Downtown Loop.
Smaller airport located on the southern part of Chicago. Mostly served by Southwest and Delta.
The Orange Line ‘L’ – Direct from Midway into the Downtown Loop for $2.25 one way ticket and operates for 21 hours of the day. It’s possible to take a cheap taxi once downtown to your hotel or transfer with a bus.
Taxi from Midway – It costs around $35 – $45 From Midway to Michigan Avenue and the Downtown Loop.
At both airports there are 3 – 7 day CTA passes that can bought with a credit card or cash. Public transportation in Chicago is easy and goes to anywhere you need. Even riding the bus or taking the L twice a day makes up for the costs with the pass. Don’t be scared of public transportation!
Shuttle Service – If you’re staying near the airport than a hotel shuttle can pick you up. You could also get a personal shuttle for as little as $16. This can be slower though as they pick up other customers along the way. If you have a big group, than this is probably the way to go if you don’t feel like taking public transportation.
- Uber does not operate from O’Hare!
- Usually takes around an hour to get into the Downtown area aka “The Loop”
- If heading to Lakeview, Lincoln Park, Logan Square, Uptown, Gold Coast, Near North, Old Town or any other neighborhood near the coast; don’t be afraid to take the buses. They come often and provide the best way from Blue Line stops to east Chicago.
Obviously flight costs vary across time and location. Summer is typically the high season for Chicago while early spring, late fall and winter tend to be the low season. Christmas, Thanksgiving, and if any major events are in Chicago, prices will be up. Budget around $200 – $500 for a round-trip flight to Chicago.
Major advantage is the Chicago is centrally located making it a 1 – 5 hour flight from most places in North America. It really is a prime weekend getaway destination.
It’s true that Chicago is also a major crossroad for travelers driving across the US. The city is a great stopover if you plan on continuing drive through Chicago. Interstates I-90, I-94, I-80, I-55, I-65, I-57, I-43 all make their way into Chicago.
Driving time from major cities:
- New York – 12 hours
- Milwaukee – 1.5 hours
- Detroit – 4 hours
- Dallas – 15 hours
- Des Moines – 5 hours
- St. Louis – 4.5 hours
- Denver – 15 hours
- Montreal – 12.5 hours
- San Francisco – 32 hours
- Los Angeles – 31 hours
- Atlanta – 10.5 hours
- Miami – 19.5 hours
- Seattle – 30 hours
- Indianapolis – 3 hours
I would not recommend taking trains or buses. They take a long time, usually uncomfortable and sometimes get into serious accidents. Amtrak and Greyhound do service Chicago though.
Unfortunately Chicago is not cheap with hotels and it’s hard to find something great on a budget. On top of that weekends tend to be the busiest so it can be hard to find a great deal.
Most tourists should stay somewhere near downtown near Michigan Ave or in the Loop. In the summer expect to pay from $150 – $300 a night for a quality hotel. Winter, Fall, and Spring you will see lower prices from around $100 – $200 a night.
Eating is actually relatively easy to stay within budget. Chicago has many great food establishments around the range of $5 – $15. Expect to pay around $15 – $30 for a mid-range sit down meal. And $30 + for a high-end meal.
Bars are priciest near Downtown and the Gold Coast. Near Lakeview and Lincoln Park, alcohol is relatively good price from around $4 – $10 depending on what you order.
Getting around Chicago is easy and I recommend that everybody buy a CTA pass for the amount of days visiting. The CTA passes work on all buses and the famous ‘L’ trains. These two combinations should get you to anywhere you need to go.
If you’re looking to change it up then Chicago has this new bike sharing program called Divvy. 7 dollars for a 24 hour pass and you can rent the bikes for 30 minute segments with an extra charge after that. Really a great way to get around quickly and on beautiful days. My recommendation is to bike to Lakeshore.
- Any Weekend in Summer
- Late Spring Weekends
Chicago is known for its variable weather. One day it can be very cold but the next it could jump back up to hot. You want to make sure to look at the forecast before you come, don’t assume anything for Chicago!
Chicago is a safe city which may surprise people. There are just very certain parts of the city that should be avoided. These include the South Side areas, just below Chinatown and West Chicago in neighborhoods near Austin. Honestly there is nothing in these neighborhoods to really see or do.
Most of your weekend will be focused in Downtown, known as the Loop, and the North side of Chicago. These are safe at all hours but be cautious late at night and early morning for pickpockets and rowdy drunk crowds. This is especially true in bar areas like Lakeview and Lincoln Park.
Downtown tends to be dead at night and I wouldn’t walk in the alleys or on the lower levels of Wacker. These tend to be sketchy and can be unsafe. The worst I’ve personally seen is the homeless threatening to beat up each other. I’ve also heard of people getting mugged on the Red Line at hours like 2 or 3 in the morning.
Like a Local
In this section I’m going to list how to travel in Chicago like a local. You’ve probably guessed that Chicago has so much more to offer than the typical sites you already know.
Lunch and Dinner
- Sultans – Cheap and fantastic Falafel
- Purple Pig – All things pig
- Alinea – Highest rated restaurant in Chicago; expensive but world-renowned
- Girl and the Goat – One of the hottest dinner choices
- Ann Sather – Swedish Cinnabons
- Wow Bao – Fast, lovely Asian buns
- Kuma’s Corner – Famous Chicago burgers
- North Pond – Farm to market upscale restaurant in Lincoln Park
- The Weiner Circle – Famous raunchy hot dog stand
- Clark Street Dog – Lakeview hot dog institution
- Giordano’s – Obligatory deep dish pizza
- Native Foods – Wonderful healthy food
- Simply It – Vietnamese food in Lincoln Park
- Pho 777 – Vietnamese pho
- Au Cheval – American restaurant
- Bandera – Southwestern restaurant in the loop
Stretching from Near North Side all the way to Edgewater, Lincoln Park is vast and offers tourists and every day locals an escape from the city. You’ll see bikers, joggers, walkers, etc, all in the park, especially on warm sunny days. Nearby are local beaches that are also busy during the summer.
Lincoln Park also has its own Zoo and Conservatory which are both free and highly recommended.
The smaller but perhaps the tower with better views is the Hancock Tower. Admission to get up to the 95th floor is free but you have to get a drink at the bar or eat at the tower restaurant. The views are stunning and one of my favorite places in Chicago.
If you happen to be on Michigan Ave, you should stop by the famous Drake hotel at around 1 – 5 pm in the afternoon for some afternoon tea. The Drake is a famous Chicago Institution and having tea in this lovely building is divine.
St. Patrick’s Day in Chicago is insane with thousands of people partying and watching the annual Chicago River turn green.
During the summer the beaches are filled with pale Midwesterners looking to get some sun. The water is cold but the beaches are warm. Try North or Hollywood Beach.
Rent a Divvy bike and ride along the Lakeshore up to Lincoln Park or back down to the Loop. On a sunny, warm day it’s a very pleasant ride with great views of the Lake and fresh breezes.
Concerts in Millennium Park
Starting from May and ending sometime in September, Harris Theater in Millennium Park offers free concerts. Bring your own booze and food!
Only from the day after Thanksgiving to Christmas; this market has a huge Christmas Tree and sells Authentic German and other European goods. Located downtown in the loop at Daley Plaza.
During winter, in front of the CloudGate, there is a small ice rink that is open for all winter. Probably, for the best experience, is during Christmas.
New park that has a skating rink, children’s play area, and wonderful area to walk around. Right next to Millennium Park.
Filled with both native and tropical plants, this Conservatory is free to see and worth a visit if you’re stopping by the Lincoln Park Zoo. On cold days the inside is still warm and humid, a good break from the outside.
Take a walk on the Lakeshore and you’ll pass beaches and the amazing Lake Michigan. A nice break from the city.
Chicago Architecture including Lincoln Park and Lakeview
Take some time to appreciate the different architecture specifically from the Gold Coast to Lakeview. Many of the buildings were built just after the Great Fire and still standing.
Located in Grant Park it’s a little further walk but if you’re heading to the southern Museums, this is a great photo stop.
Some of the biggest comedic names began their careers at Second City and went on to shows like MadTV and SNL. This is truly a Chicago Institution and should be considered if you’re looking for laughs.
Right next to the Lincoln Park Conservatory this tiny lily pool takes you out of the streets of Chicago and puts you into this wonderful manicured garden. It’s easy to miss but worth a visit.
In the Downtown Loop, it’s a beautiful building that is free to enter and has one of the most beautiful glass domes.
Chicago has a major nightlife scene and people here really do love alcohol. And because it’s a large city there really is something for everybody and that could range from Downtown upscale to Lakeview dive bar.
Lakeview is the place to go out because it’s one of the densest and most vibrant parts of the city. Mostly made up of young professionals, on the weekends the bars and restaurants are packed. Seriously streets like Broadway, Halsted, Sheffield and Racine have hundreds of bars to choose from. Lakeview is known to be more down to earth, so you’ll see the majority of bars are classical American pub style. Most bars here are tiny and dark but all have this fantastic intimate vibe. This is a very good part of time for bar hopping and drink to the wee hours.
Lively and in Lakeview. This is really the center of the bar scene, especially on Clark street. On Friday, Saturday and Sunday this area is packed with people and is more geared towards young professionals letting loose. This area also is packed in the summer when Cubs game are on or when any Chicago sports team is doing well.
Really this is my scene because this is gay central. There are over 50 gay bars in the area with most of the scene directly in Boystown on Halsted street, starting from Belmont and working way north past Addison. Chicago gay men are stunning and you’ll see a lot of tall midwestern men. In the summer the bars and restaurants are packed and the clubbing scene could end as late as 4 or 5 in the morning.
This area is actually more for the college crowd since there is DePaul University nearby. But Lincoln Park is also a great alternative with many restaurants and bars to choose from. I love this area because of the old architecture and windy neighborhoods.
Logan Square/Wicker Park/Bucktown
The area where I would least likely visit since it is further west. But if you’re a hipster and want to experience that, Logan Square is the place to be.
I would specifically start at Logan Square park with several unique bars around there like Lost Lake and then work your way down Milwaukee Ave. There are tons of bars along the way, some being elegant and others more divey.
Downtown/Gold Coast/Near North Side
Where most of the tourists stay this area ironically becomes quite dead at night. But not everything is closed, especially around the lake area and north of the river in Near North Side and Gold Coast. The drinks are more pricey here and perhaps a more pretentious vibe but it can be a lot of fun, especially if you have fantastic views of the downtown skyscrapers.
Sandwiched between Lincoln Park and Gold Coast there isn’t as many bars as other areas but still some good choices.
Just west of the Chicago River lies the West Loop and thanks to Oprah it has now become a safe and trendy spot to hang out. It’s popular with the after work crowd.
Traveling outside of Chicago and you will need a car. There are trains but they take a long time and you’re not able to go to most scenic places around the area. Rent a car from the airports or rental cars in the downtown area.
From my personal experience, there is plenty to do outside of Chicago if you know where to look. However first time weekend travelers to Chicago, I would focus more on staying in Chicago.
Not too far away is Michigan which is a fantastic state to visit. By car you could reach the Michigan border within 2 hours from Downtown. My recommendations would be Saugatuck, Grand Rapids, and the Upper Peninsula.
Just north of Chicago lies Wisconsin and the cities of Milwaukee and Madison. These two cities and their surroundings are wonderful day trips with touring, outdoor camping and hiking, festivals, bed and breakfast, etc…
There isn’t much to say or do in Indiana besides some outlets stores and their famous dunes near Michigan City. Indianapolis is only about a 3 hour drive from downtown Chicago and has some yearly festivals worth considering.
If you’re looking for some local areas to hang out you could try Evanston which is just north of Chicago and has somewhat of a walkable downtown. Western cities to consider include Schaumburg, Naperville, Elk Grove, Arlington Heights, Bolingbrook and Downers Grove. Metra service does run to all of these cities, usually making stops in their respective downtowns.
In my opinion there isn’t much of a draw to go out there so I wouldn’t bother. There are outlets and shopping centers and maybe the yearly city festival.
Exceptions include the Botanical Gardens in Glencoe.
Etiquette standards follow the rest of the United States.
For travelers outside of North America, in Chicago, it’s essential that you learn how to tip. 10 – 20% is standard for most places. The most common encounters where you need to tip will be at sit down restaurants, valet service, and sometimes tipping hotel staff, and taxi rides. You automatically pay taxes on clothes and shopping. It’s standard in the US and it’s essential that you tip when it’s necessary!
But don’t be confused. Not all places require tip, like when you’re ordering fast food or a to-go restaurants.
Americans are actually friendly and more open to talk to people. I know many foreigners find this sometimes uncomfortable and say that Americans talk to much or are too friendly. For example in stores it’s common to get a greeting followed up by “can I help you with anything?” It’s just American customs!
Also most Americans don’t speak another language. This is an embarrassing fact but it actually doesn’t mean we don’t care about foreigners. If an American happens to meet a foreigner, most would try to be helpful but very few actually speak a language that could help out. Just be patient with us!
Chicago is pretty far from most other major cities. If you’re thinking you’re going to get away and drive to New York or Washington DC, think again. Both are around 10 hours away by car. The US is a vast place and unfortunately it can be both expensive to fly or drive.
My Weekend in Chicago Itinerary
In this section I’m going to list out the perfect Chicago weekend for me. This is meant to help inspire a realistic goal for your weekend here and I’m here to help make sure you do the most important things. Typically a weekend is from 3-4 days but people may have an extended weekend for up to 5 days, so I’ll keep in mind a range from 3-5 days.
This is a curated guide and not meant to be followed strictly. This is just merely a suggestion of the things I would see in Chicago in retrospect. If you’re in town for holidays like Christmas or St. Patrick’s Day then trade out some of these other events to go to things like Christkindlmarkt or to see the St. Patrick’s Day Parade.
Assuming you’re flying the night before or early morning, most people are generally a little fatigued on their first day, and Chicago is not a city where you want to push yourself too hard. After you drop your luggage off, it’s time to hit the street. Make sure you buy your CTA pass, either at the airport, at a nearby Walgreens or a major L stop.
We will say that the average person will start their day at around 9 – 10 ish give or take. It’s better not to rush it on the first day.
Spend about an hour roaming the parks, take a picture with the CloudGate sculpture, and visit the Buckingham Palace. Stroll over to the newly built Maggie Daley Park and see the new ice skating rink. This is downtown Chicago and really an essential visit for anybodies first visit.
Chicago Culture Center: 15 min
Right next to the CloudGate, there is the Chicago Culture Center, which is free to enter, and possesses one of the most beautiful glass domes inside. You only need around 15 minutes to visit.
Wildberry for Brunch: 1.5 hr
Stroll up to Wildberry for a late breakfast, brunch/lunch, at the best pancake and breakfast restaurant in Chicago. Reasonably priced and huge portions, this placed is packed so you’ll need some extra time just to wait. But you’ll be thankful you did, as it’s simply a gratifying meal and truly memorable. It’s located just north of Millennium Park.
Art Institute of Chicago: 2 – 3 hrs
This one requires a lot of standing but from Wildberry it’s only a 5 minute walk. Use your City Pass to get in. The Art Institute is particularly strong in impressionist works and a couple of famous paintings, sculptures, and pieces of work that shouldn’t be passed up.
Michigan Ave Walk: 1 – 3 hrs
Some people love shopping and others not so much. But I recommend that people still walk on the Famous Magnificent Mile. It’s where all the major shopping and many food is located. There are a lot of areas along the way that are a great for sitting down if you need a rest.
Purple Pig for Dinner: 2 hrs
Located just north of the River on the Magnificent Mile, this is a very popular dinner restaurant and highly praised. Everything at this place involves pig, as you could have guessed, and everything is served in a tapas family sitting format. In fact you could be sitting next to other people. Get here early to avoid the wait.
Signature Lounge Bar at Hancock: 1 – 2 hrs
Cap off your night with a visit to the 95th Signature Lounge at the Hancock Tower. This place is actually one of my favorites in Chicago because of the lovely views of all the city. And you don’t have to pay to go up, rather just pay for drinks or food at the bar or restaurant. I think it’s a better deal than the popular Willis Tower Experience.
Optional Drinks in Goldcoast or Near North Side: Finish the night
This tends to be the more expensive part of town but a lot of unique bars in this area offering a good night out drinking. Or perhaps you want to catch up a game, plenty of bars with TVs. My recommendations would be I/O Roofscape, Le Bar Chicago, ENO Wine Bar or Timothy O’Tooles.
Yolk Breakfast: 2 hrs
Head over to one of the best breakfast restaurants in Chicago! They have many locations so doesn’t matter where you’re starting your morning but you should get there early as it can be a wait and they only sit a table when your whole party has shown up. It is worth it though, with huge meals and a very good strawberry orange juice.
Bike or Ride Up to Lincoln Park: .5 – 1 hr
Depending on how fast you want to get up to Lincoln Park, you could take a Divvy bike on Lakeshore if it’s a nice day, or use the CTA to get up to Lincoln Park. If using a bus, take the 151 from Michigan Ave north until Lincoln Park Zoo. If you have a smart phone just download Google Maps App for a schedule and guide to get you there.
It depends on how long you want to see animals or plants but this is very pleasant place to hang out at. Going in morning/afternoon helps too as it’s not as crowded. For me I could spend max 1 hour at the zoo and like 45 minutes to an hour at the Conservatory. If it’s a really nice day I would spend more time outside or on the Divvy bike, traveling through the park.
So I gave a large selection to choose from because I know not everybody has the same taste. These selections are mostly in Lincoln Park and Lakeview and are within walking distance or a short bus ride. All are great choices and it just comes down to what you’re in the mood for.
If you’re really feeling outdoorsy and it’s a beautiful warm day, head over to Hollywood or North Beach. North Beach is near Lincoln Park and can easily be reached on foot or on a bike. Hollywood Beach is a little further and it’s better if you take the bus, red line, or bike on Lakeshore.
This is if you need an excuse to sit down or feeling like you need some sweets to get to dinner. I would stop in at Café Vienna and La Fournette, both in Lincoln Park. Café Vienna is known for it’s Austrian pastries while La Fournette is known for it’s French desserts like macaroons. I love a great sit down, relax, drink coffee and eat snacks type of restaurant!
Architecture Tour: 2 – 2.5 hrs
You’ll need about 2 hours to 2.5 hours to buy your tickets or commute to the Chicago river, which straddles the Loop and Near North Side. Most people buy their tickets in advance, as they could be sold out but it’s possible to walk up and by them the day of. They run from late morning all the way into the night. Either day or night, you’ll get an education on Chicago architecture and beautiful shots of the city.
Okay so the first one is a Chicago institution and can be very busy. You can order your deep dish pizza when you put your name in because it takes so long to make a deep dish pizza. By the time you sit down your meal should be almost ready.
For the Girl and the Goat you’ll need a reservation before you come to Chicago or get lucky and find a seat on the few seats they reserve for walk-ins. One of the most popular restaurants in Chicago now, it’s certainly worth a wait and may convince you to come back to Chicago.
Other ideas would be:
Night out in Lakeview/Lincoln Park: Finish the night
Spend the rest of your night in the neighborhoods of Lakeview and Lincoln Park to bar hop. Try Wrigleyville or Boystown in Lakeview or northern part of Lincoln Park. Check “Going Out” for bar suggestions.
Doughnut Vault: 1 hr
Very tasty doughnut shop located in Near North Side near Merchandise Mart. They start selling early in the morning until they run out and there usually is a line. You can look on their website for their specials and updates on how many doughnuts they have left.
Shedd Aquarium: 2 – 3 hrs
Take a bus to the Shedd Aquarium and use your City Pass to skip the lines and get right in the museum. The aquarium has lived performances, guides teaching the public and displays of all different types of aquatic animals from around the world.
Field Museum: 2 – 3 hrs
Located right across from the Shedd Aquarium, the Field Museum ranks as one of the best museums for science and history. It is also known for the largest T-Rex display in the world. Use your City Pass to skip the lines and get right in.
Bandera: 2 hrs
Head back on Michigan Ave and eat at Bandera, a Southwestern American restaurant overlooking Michigan Ave. If you want to come back at night they have nightly jazz.
Willis Tower: 1.5 hrs
Head back into the Loop to the Willis Tower which is formally the Sears Tower. For about 20 years this was the tallest tower in the world and with your City Pass you can learn about why it was built and how. IT truly is a testament to this cities obsession with architecture and skyscrapers. While you’re up at the top get a picture in one of the clear glass windows overlooking the western side of the tower.
The Second City: Finish the night
Finish your night and weekend at this Chicago Institution. Second City is a comedy show and has several shows to choose from depending on when you want to go. Look online for tickets in advance.
If you’re staying longer may I suggest that you rent a car one day and head to Michigan or Wisconsin. Milwaukee and Madison is not too far away and both have weekend markets selling Wisconsin goods. Wisconsin is also known for its outdoors and has beautiful lakes, ski resorts and bed and breakfasts.
Michigan offers basically the same as Wisconsin and is about the same distance. You can visit Saugatuck, Grand Rapids and New Buffalo. There are several nice beaches and bed & breakfasts; perfect for a one day getaway.
The Obvious Sights
Chicago has many iconic sites which is why I wanted to shortly listed them. Some of these essential but since most people know what these are I’m not going to spend too much on them.
Also known as the Chicago Bean, it’s located right near the lake in the Loop. It’s touristy but an essential tourist sight and a really great sculpture. Many tourists like to begin here since it is such an iconic location. And it’s free!
Most people will go to this tower since it was formerly the largest tower in the world and the tallest tower in Chicago still. However it’s kind of expensive ($32), and very touristy. I would still go here, using your City Pass because of what it means to Chicago. It does offer great views but my personal suggestion is to try Signature Lounge at the Hancock Tower.
It is the première art gallery and although it’s also expensive to get into, it is worth the ticket. If you plan to do many museums then just buy the City Pass, which is much cheaper than paying for each site and museums.
In the South Loop, right on the Lake, the Field Museum is also one of the best museums in Chicago and is included in the City Pass. It is mostly natural history and has the world’s largest T-Rex on display.
Navy Pier is free and is, I guess, an iconic symbol of Chicago however it lacks excitement. There is a large ferris wheel where you have to pay to go up and a boardwalk with typical boardwalk food but that’s about it. There is a great IMAX right at the entrance as well.
A huge aquarium displaying all types of fishes and marine life. Also expensive to get into but if you have the City Pass it’s included in the pass. I’ve noticed it can be crowded with kids, sometimes making the experience less than ideal.
At the end of the peninsula, near the Field and Shedd Museum, this focus on Space. This isn’t essential but is included in the City Pass.
Here you’ll find a large park to walk around, and the Harris Theater where they put on summer performances. Free and really lovely.
The most impressive thing here is the Buckingham Fountain. The park is also lovely to walk around.
Located on the North and Southern edges of the Chicago River, the Architecture Tours are touristy and a tad expensive but fun and relaxing. You get a tour of all the buildings along the river plus the boats go through the docks and out on to Lake Michigan.
Where many hotels and most of the shopping is located. These could range from department stores to high-end boutiques.