For those who’re planning an extended weekend journey to the Windy Metropolis and aren’t fairly positive what to do, maintain studying for our epic 3 days in Chicago itinerary!
Whereas Chicago is the Third-largest metropolis within the US, it’s usually ignored by travellers who jet for one of many coasts.
In my view, Chicago is the most effective metropolis within the nation. New York and LA are nice and all, however I’ll gladly take the pleasant Midwestern vibe of Chicago as an alternative.
Located on Lake Michigan, the Chicago skyline is among the most stunning on this planet. In spite of everything, it was right here that the primary skyscraper was inbuilt 1885!
There’s a lot happening right here that you may spend a lifetime there and by no means run out of issues to do.
With a stable Chicago itinerary, you may positively try the most effective of town in 3 days. Let’s get to it!
How you can Spend a Excellent 3 Days in Chicago Itinerary
Our 3 days in Chicago itinerary contains:
- Millennium Park
- Shedd Aquarium
- Skydeck Chicago
- Discipline Museum
- Adler Planetarium
- Artwork Institute of Chicago
- 360 CHICAGO Statement Deck
- Navy PierMuseum of Science and Trade
- Ferris Wheel
- Crown Fountain
- Cloud Gate
- Willis Tower
- Grant Park
- Magnificent Mile
- Lincoln Park
In search of extra superior issues so as to add to your Chicago itinerary? Remember to learn our information to the finest issues to do in Chicago!
Journey Ideas for Visiting Chicago
When to Go to Chicago
Step one in determining what to do throughout your 3 day Chicago itinerary is planning if you’ll go to.
Winter in Chicago will be painfully chilly, which might positively put a damper in your journey. Until you take pleasure in frigid temperatures and chilly, biting wind, I like to recommend skipping out on December-March.
Your finest wager is to go to Chicago between Could and October. It will get sizzling and crowded in the summertime, however there’s a lot happening that it’s value coping with these minor inconveniences.
Chicago CityPASS
One other enormous tip I’ve earlier than you go to Chicago is to buy a Chicago CityPASS.
Basically that is only a multi-use ticket that truly saves you a bunch of cash (50% to be exact!) on many nice Chicago sights.
You purchase the cross for USD$109, and it contains entry to the next:
- Shedd Aquarium
- Skydeck Chicago and
- Discipline Museum
- Adler Planetarium or the Artwork Institute of Chicago
- 360 CHICAGO Statement Deck or the Museum of Science and Trade
Better of all, these entrances are principally specific or premium tickets included with the CityPASS, which means it not solely saves you cash however saves you time as properly.
We extremely advocate you decide one up when utilizing our Chicago itinerary to benefit from your time within the metropolis.
Getting Round Chicago
Fortunately, getting round Chicago is a breeze because of the CTA community of practice and bus traces. Chicagoans seek advice from the practice because the “L” as a result of it’s totally on “el-evated tracks.”
For those who’re spending 3 days in Chicago, your finest wager is to only decide up a vast CTA cross. These price $20 and are added to a Ventra card.
You possibly can decide up a Ventra card at merchandising machines for $5 and it’s credited again to your account after you register the cardboard. Learn all about getting round Chicago on the CTA web site.
You possibly can rely on the CTA getting you as far south because the Museum of Science and Trade all the way in which north to Lincoln Park.
Or think about leaping on and off the open-top bus that may take you everywhere in the metropolis!
Within the metropolis middle, plenty of Chicago sights are all inside strolling distance as properly.
Now that among the logistics are taken care of, let’s get this present on the street to your 3 day Chicago itinerary!
Day 1 – Morning
For day 1 of your Chicago itinerary , you’ll must hit the bottom working if you wish to maximize your time.
Get a pleasant early begin, crush a considerable breakfast and a few espresso, and prepare to rock.
Loop Strolling Tour
The easiest way to kick-off your Chicago itinerary is by taking a strolling tour of the Loop. This space of downtown is the place you’ll discover a majority of the sights in Chitown.
You may have a number of choices for exploring the Loop. For those who take pleasure in assembly individuals and getting the perception of a neighborhood information, you may join one of many many choices with Free Excursions by Foot.
If it’s your first time in Chicago I recommend becoming a member of their 10 AM tour of the Loop and Millennium Park. Or should you’re actually into structure, try their 10:30 Start of the Skyscraper tour. Each are glorious choices!
Those that choose a DIY strategy can try the numerous self-guided excursions of Chicago from MetroWalkz. This Structure/Loop tour makes for a unbelievable introduction to town and is fairly simple to observe.
Whichever possibility you select, you’ll get to see among the most iconic locations within the metropolis in just some brief hours. A couple of of the highlights embody the historic begin of Route 66, the nice Chicago Theatre.
Day 1 – Afternoon
At this level, the order during which you do issues is dependent upon which kind of tour you selected. You will be versatile, because it’s a brief stroll between the subsequent couple of locations.
Earlier than we transfer together with the three day Chicago itinerary, it’s time for lunch! For those who’re down within the Loop and also you need to attempt a neighborhood favorite, the selection is simple…
Chicago Scorching Canine
There are numerous eating places to select from within the Loop, however you don’t need to journey all the way in which to Chicago to get caught consuming at some overrated chain or overpriced vacationer entice.
Al’s is a basic native joint serving up the well-known Chicago model sizzling canine and their specialty Italian beef sandwiches.
One factor to know, a Chicago canine is an all-beef canine on a sesame seed bun. It comes topped with tomato, chopped onions, pickled peppers, relish, a pickle spear, and yellow mustard. Fairly merely put, it’s heaven on a bun.
I might be remiss if I didn’t additionally point out Portillo’s. In addition they make among the best Chicago model sizzling canine on the market.
Whereas they’re a bit out of the way in which for in the present day’s itinerary, maintain them in thoughts should you’re craving one other sizzling canine throughout your 3 days in Chicago (and belief me, you’ll).
Millennium Park
Even should you visited in your strolling tour, it’s value it to double again to Millennium Park for additional exploration.
There’s a whole lot of cool stuff to see right here, together with the Crown Fountain and the Cloud Gate.
The latter is often known as “The Bean” and is considered one of Chicago’s hottest locations to take photographs within the metropolis. Don’t neglect to snap that quintessential Chicago shot for the ‘gram and carry on transferring.
Different Chicago sights you need to see in Millennium Park embody the Jay Pritzker Pavilion, the BP Pedestrian Bridge, the Chicago Cultural Middle, and the Lurie Backyard.
You possibly can simply spend a few hours in Millennium Park, particularly on a pleasant day.
Buckingham Fountain and Grant Park are inside this similar space as properly if you wish to maintain exploring on foot.
Artwork Institute of Chicago
Whereas there’s loads of wonderful public artwork within the Loop, you may’t prime the gathering on the Artwork Institute of Chicago. Artwork lovers will certainly need to embody this on their 3 day Chicago itinerary.
Tucked away on Michigan Avenue on the south finish of Millennium Park, the Artwork Institute of Chicago has a severely spectacular assortment right here and there are all the time new reveals that includes trendy and up to date artwork.
Profit from your Chicago CityPASS to realize quick entry into the Artwork Institute of Chicago.
The museum is open each day from 10:30 AM to five PM and stays open till 8 on Thursdays.
Day 1 – Night
Earlier than the day turns into night time, it’s time to hustle over to your subsequent vacation spot of your 3 day Chicago itinerary. Attempt to time it excellent so that you make it there about an hour earlier than sundown. Belief me, it’s value it!
Willis Tower
Whether or not or not you hit the museum, your subsequent cease must be the Willis Tower. That is considered one of Chicago’s most iconic skyscraper within the metropolis that invented them!
Previously referred to as the Sears Tower, this was the tallest constructing on this planet for 25 years. It stands at 442 meters (1,450 ft) tall and is at the moment the 2nd-tallest constructing within the US.
For those who plan to go to Chicago in 3 days, you positively must examine the Willis Tower off your to-do record.
Head to the 103rd flooring to entry the Skydeck Chicago and step out onto “The Ledge” – a glass balcony that allows you to look straight down. You’ll need to see views of town from this spectacular perspective!
Don’t neglect, the most effective time to go to the Willis Tower is simply earlier than sundown. It stays open till 10 PM from March by means of September and tickets price $25 for adults and $17 for kids.
As soon as once more although, no must pay additional for a ticket, as a result of the doorway to the Skydeck Chicago is included together with your CityPASS.
Dinner and Drinks
To have fun making it by means of an enormous day 1 of the Chicago itinerary, it’s time for supper and drinks! With regards to wining and eating, the world actually is your oyster within the Loop.
After such a giant day, you could need to name it a (considerably) early night time. We’ve nonetheless acquired a whole lot of floor to cowl with this 3 days in Chicago itinerary! After all, if you wish to exit and rage, go for it!
Day 2 – Morning
For those who don’t have breakfast included at your resort, I extremely advise you to start out day two off at Yolk’s South Loop location.
That is the proper spot to load up with a giant breakfast and low earlier than one other massive day within the metropolis. Go forward and carb up – there’s going to be a whole lot of strolling in the present day!
Museum Campus
After breakfast, stroll throughout the road to take a look at Agora – a sculpture composed of 106 headless figures.
Hold strolling east in direction of Lake Michigan to achieve the Museum Campus. Right here you’ll discover the Discipline Museum, Shedd Aquarium, and the Adler Planetarium.
With simply 3 days in Chicago, you’ll most likely need to simply go to one. Having been to all three, I’ll solid my vote for the Discipline Museum.
There are such a lot of cool reveals on the Discipline Museum they usually’re all the time altering.
In the intervening time, they’ve: Inside Historic Egypt, Chicken’s of America, and Brewing Up Chicago, amongst others. Examine their web site to see what’s happening earlier than you go to.
Tickets for the Discipline Museum price $26 for adults and $19 for kids for fundamental admission.
For those who acquired the CityPASS, your admission is included in all three, except you hit the Artwork Institute on day one. For those who’ve acquired the cross, you would possibly as properly hit the aquarium as properly.
To be sincere, the aquarium is fairly candy. Even should you don’t have the CityPASS, you need to most likely attempt to squeeze it in.
Tickets are $40 for adults and $30 for youths and also you’ll positively get your cash’s value.
Day 2 – Afternoon
There are a number of cafes and meals stands across the museum campus, so go forward and seize a snack and a drink earlier than powering on.
That is a type of days the place it’s finest to have a giant breakfast and dinner and simply graze through the day. Once you’re attempting to cross off so many issues to do in Chicago in 3 days, you gotta maintain transferring!
Grant Park
The museum campus is the southern a part of Grant Park. Referred to as “Chicago’s Entrance Yard,” this huge inexperienced area is to Chicago what Central Park is to NYC.
Take a stroll by means of the park to see such landmarks because the Buckingham Fountain, the Rose Backyard, and the Seated Lincoln Statue. There are many benches if you must sit down and chill for a bit.
Grant Park additionally hosts among the largest occasions within the metropolis, such because the Style of Chicago and Lollapalooza.
Some are free and others price a whole bunch of {dollars}, so make sure you examine the calendar of occasions to see what’s taking place earlier than you e book your journey.
Riverwalk or River Cruise
Hug the coast and maintain strolling north alongside the Lake Michigan till you attain the Riverwalk. This scenic pedestrian path alongside the Chicago River is the proper place for a leisurely stroll.
In case your ft are feeling a bit drained from all of the strolling, you may benefit from the spectacular Chicago structure on this unbelievable river cruise as an alternative.
Taking within the sights alongside the Chicago River is certainly one of many prime issues to do in a 3 day Chicago itinerary.
Wendella Boats has an structure river cruise that comes extremely beneficial. Be sure you have your digital camera for this one, as you’ll get some epic views of town.
Day 2 – Night
I’m positive you’re able to eat your hand by now, however you’ve simply acquired to soldier on for a bit longer. Belief me, it’s going to be well worth the wait!
Magnificent Mile
On the opposite aspect of the Chicago River, you’ll discover the Magnificent Mile, a brief stretch of Michigan Avenue in downtown Chicago. That is town’s premier industrial district, stuffed with high-end outlets, good eating places, and boutique lodges.
Alongside the Magnificent Mile, you’ll additionally see a number of historic skyscrapers, such because the Wrigley Constructing, Tribune Tower, and the Previous Watertower.
The latter is residence to the Metropolis Gallery, which has Chicago-focused pictures reveals. It’s completely free to go to, so you could as properly try whilst you’re within the space.
Even should you’re not doing any procuring, it’s value a fast stroll alongside the well-known Michigan Avenue. That’s as a result of it’s main you to…
Chicago Deep Dish Pizza
You had the new canine on day one, so it’s time to dig into some Chicago-style deep dish pizza.
Because it’s cooked in such a deep pan, a Chicago-style deep dish pizza will be filled with mountains of cheese. After all, you may add no matter different toppings you want as properly.
Now you see why I’ve been torturing you by making you stroll round all day ready for dinner! This deep dish pizza is severely scrumptious and filling, so I needed to ensure you may at the least have a number of slices.
There are many locations cooking up Chicago-style deep dish pizza, however I introduced you right here as a result of two of the most effective are simply accessible.
Get to the nook of Michigan and Superior and you’ve got an essential option to make. Take a left and also you’ll go to Giordano’s. Hook a proper and also you’ll be at Gino’s East.
Simply go forward and flip a coin since you win both means. Each locations are legendary for his or her deep dish pizzas, so you actually can’t go flawed.
Not removed from the Magnificent Mile, you’ll discover Navy Pier. For those who’re spending 3 days in Chicago on an extended weekend, that is the proper place to be on a Saturday night time.
First up, you may take a journey on the Centennial Ferris Wheel. Tickets price $18 for adults and $16 for kids, however it can save you a couple of bucks should you e book on-line.
From the tip of Could till the tip of August, Navy Pier additionally hosts bi-weekly fireworks reveals. These occur on Wednesdays at 9:30 PM and Saturdays at 10:15.
To absorb the spectacle, you will discover a spot to face on the Navy Pier or join a night cruise. Having fun with the fireworks as you cruise round is a superb addition to your Chicago itinerary.
Select Your Personal Journey
If in case you have any gasoline left within the tank after all the actions on the Navy Pier, congratulations! I simply ran you ragged throughout Chicago on day two. That’s why it’s time to decide on your individual journey!
For a lot of, that may most likely contain grabbing an off-the-cuff drink from the resort bar and getting some sleep. That’s completely wonderful. I’m attending to the age the place that seems like an ideal Saturday night time!
For the younger whipper-snappers amongst us, you’re most likely itching to take pleasure in a giant night time out in town. Go for it, you loopy children!
Your choices are limitless. There’s reside music of all varieties, comedy golf equipment, and nearly each sort of bar beneath the solar.
Whether or not you’re on the lookout for a speakeasy that whips up inventive cocktails, an aesthetic wine & jazz joint, or only a good ole’ original dive, you will discover it in Chicago.
On this a part of town, considered one of my private favourites is Three Dots & a Sprint. This superior tiki bar has a formidable choice of cocktails that may transport you to the Caribbean very quickly.
For those who’re going to go exhausting one night time, that is the one to do it! Bars in Chicago sometimes shut at 2 AM, however there are a number of that keep open as late as 4 on the weekend. You’ve been warned…
Day 3 – Morning
How early the final day of your 3 day Chicago itinerary begins relies upon fully on how late your night time went!
Those that already remorse ordering that final spherical could must sleep in a bit and smash a greasy brunch, whereas the go-getter set who truly slept will likely be up and at them. Life is all about selections, individuals!
No matter you probably did the night time earlier than, get some meals and caffeine in your system and get on the market to wind down this 3 day Chicago itinerary.
Museum of Your Selection
Our third and ultimate day in Chicago begins off with a leisurely museum go to. Inside a number of blocks of one another, you may take your decide between three glorious museums.
Artwork fanatics will gravitate in direction of the Museum of Up to date Artwork, which highlights post-WWII artwork.
These extra excited by structure and antiques could need to hit the Richard H. Driehaus Museum. It’s in a restored Nineteenth-century mansion and brings you proper again to the Gilded Age.
Chicago could be very a lot a sports activities metropolis, as individuals listed here are very keen about their groups. Take a look at the Chicago Sports activities Museum, which is stuffed with memorabilia and loads of enjoyable reveals.
360 Chicago
I do know I already despatched you to the Willis Tower on day one, nevertheless it’s nonetheless value a visit to John Hancock’s 360 Chicago on Michigan Avenue.
This statement deck on the 94th flooring of the John Hancock Constructing supplies a complete totally different perspective on town that you’ll positively need to see.
Plus, should you purchased a CityPASS your admission to the John Hancock constructing is already included! For those who didn’t seize the cross, a ticket is $25 for adults or $15 for kids.
Those that are feeling adventurous (and never hungover) could need to take a journey on Tilt – Chicago’s highest thrill journey.
For those who want some hair of the canine as an alternative, you may seize a ticket that features your selection of grownup beverage. Sunday Funday!
For those who don’t buy the Chicago CityPASS think about buying this ticket to benefit from the views from the 94th flooring of the John Hancock constructing’s 360 Chicago.
Day 3 – Afternoon
When you come down from 360 Chicago in John Hancock constructing, you could have loads of choices for lunch. Inside a number of blocks, you will discover Cuban, Vietnamese, Mediterranean, and the Chicago staple of deep dish pizza.
In order for you a lunch with a view, think about consuming at The Kennison. This upscale bar and restaurant affords sweeping views of Lincoln Park. The menu is trendy American they usually have plenty of wonderful cocktails and drinks.
Lincoln Park
Hop on the bus, order an Uber, or stroll half-hour to our subsequent vacation spot – Lincoln Park.
There’s so much to do on this enormous park on the shores of Lake Michigan. North Avenue Seashore is on the south finish.
On a lovely day in Chicago, it’s exhausting to beat lounging on the seashore and swimming within the lake. You may also play some seashore volleyball and hire a SUP or bike if you need some extra exercise.
Within the center is the Lincoln Park Zoo, which is completely free to go to. Sightseeing will get costly, so this superior free attraction is certainly one of many prime issues for any Chicago itinerary.
After such an action-packed 3 days in Chicago, you need to positively simply take it simple and luxuriate in all that Lincoln Park has to supply. You’ve coated some critical floor in a short while, so congrats on that!
Day 3 – Night
At this level within the journey, you could have completely crushed 3 excellent days in Chicago. Order a celebratory drink or two and luxuriate in your final night within the metropolis!
What you select to do together with your ultimate night time all is dependent upon if you’re visiting and what your pursuits are. That’s why it’s time as soon as once more to…
Select Your Personal Journey
In an ideal world, the Cubs can be taking part in an evening recreation while you’re visiting Chicago. You possibly can head north to Wrigley Discipline and luxuriate in America’s pastime on the 2nd-oldest ballpark within the nation.
The Cubs play about 80 residence video games between April and September, so there’s a very good probability they’ll be on the town when you’re. Even should you’re not a baseball fan, I like to recommend hitting a recreation if in any respect attainable.
Chicago truly has two MLB groups. However the White Sox ballpark is means south of the place you’ll be on day three and never well worth the journey should you ask me.
For those who’re making a visit to Chicago between October and April, you might be able to catch the Bulls (NBA), Blackhawks (NHL), or the Bears play a house recreation. Examine their schedules to see what’s happening if you’re on the town.
Those that choose a very good giggle can head again to the south finish of Lincoln Park. Only a block away, you’ll discover three of town’s finest comedy golf equipment – Second Metropolis, UP, and Zanies.
I just about all the time journey to Chicago for reside music, so I’m going to toss that in right here!
The town has an epic music scene and there’s all the time one thing taking part in right here. Whether or not you’re into rock, hip-hop, jazz, digital, blues, pop, or no matter it’s you wacky Millenials hearken to lately, there’s a present for you.
I often examine Jambase to see what reveals are taking part in.
Cheers!
Congratulations, my pal. You made it by means of an insane 3 days in Chicago itinerary and skilled the most effective that the Windy Metropolis has to supply.
I’d say that requires a toast! If you wish to end up with a real Chicago expertise, order a shot of malort. This notorious Chicago liquor is fairly exhausting to explain, so I’ll let its label do the work:
“Malort has the aroma and full-bodied taste of an uncommon botanical. Its bitter style is savored by two-fisted drinkers.”
I’m not going to sugar coat it – these items is terrible. It’s a ceremony of passage right here in Chicago, although. Eat the new canine. Drink the malort. Reward be to Ditka. You’re now somewhat bit Chicagoan.
After you end that putrid shot of malort, swap to a scrumptious Chicago craft beer. There are many selections right here, together with Lagunitas, Revolution, and Goose Island.
I hope you loved this huge tour of Chicago!
From Navy Pier, to Millennium Park, the Chicago riverwalk, the well-known Chicago sizzling canine and extra, visiting Chicago isn’t uninteresting.
Hopefully this 3 day Chicago itinerary has been inspiring and provides you an concept of what to do within the Windy Metropolis.
Chicago Itinerary Journey Information
Now that what to do with an extended weekend in Chicago, I’ve gone forward and put collectively a mini-guide to this superior metropolis that will help you resolve the place to remain, the place to eat, and naturally the place to drink!
The place to Keep in Chicago
You’re most likely questioning the place to remain, particularly if it’s your first time in Chicago.
Most first-time guests select to base themselves in downtown Chicago, and for good purpose. Listed here are numerous choices for lodging, sightseeing, eating, and nightlife.
As you would possibly anticipate, staying downtown comes with a price ticket. Different standard locations to remain which might be a bit cheaper embody River North, Lincoln Park, Bucktown, and Wicker Park.
With regards to locations to put your head, Chicago has all of it. The town has 5-star luxurious lodges, quaint B&Bs, dingy motels, enjoyable hostels, and loads of choices on websites like Airbnb.
Listed here are a number of choices to go well with all budgets:
Greatest Hostel in Chicago – HI Chicago
Hostelling Worldwide is a trusted identify in backpacker lodging, and their downtown Chicago location is certainly the most effective hostel for visiting Chicago.
They’ve a number of totally different choices for each non-public and dorm rooms. You may get a bunk for beneath $40 an evening right here – a steal for this unbelievable location.This features a free breakfast, they usually even have free strolling excursions through the day and free actions at night time.
That’s not all, although. They’ve additionally acquired an enormous lounge with a ping pong desk and a TV room with loads of films. Better of all, this hostel is environmentally-friendly. They’ve reusable merchandise within the kitchen and recycling factors throughout the constructing.
Greatest Mid-Vary Lodge – Congress Plaza
This historic downtown Chicago resort dates all the way in which again to 1893. Don’t fear – it’s had a number of updates through the years!
You actually can’t beat the placement of this place. I often stick with pals in additional residential neighbourhoods, however that is my go-to spot once I need to be in the course of all of the motion.
From right here, you’re simply throughout the road from Grant Park. Most of the rooms right here even boast a pleasant view of Lake Michigan. With rooms beginning as little as $115 an evening, it’s a reasonably superior deal staying right here.
Greatest Luxurious Lodge – Peninsula
The 5-star Peninsula Chicago was lately named the 2nd finest resort within the nation by US Information & World Report. This place is fancy, individuals!
It’s positioned proper on the Magnificent Mile, so it’s surrounded by high-end outlets. That is positively the place the fabulous individuals keep.
Along with the tremendous swanky rooms, you may benefit from the resort’s three totally different eating places and its spectacular health centre.
Taking on the highest two flooring of the constructing, it encompasses a 25-meter pool and an award-winning spa. Rooms begin at round $600 an evening right here.
The place to Eat and Drink in Chicago
I’m very lucky to have a very good pal who’s closely concerned within the hospitality scene in Chicago.
I reached out to him to get an inventory so as to add to this information. He’s by no means executed me flawed with meals & drink suggestions, so you may take these to the financial institution the subsequent time you go to Chicago!
Brunch/Lunch
- Dove’s Luncheonette
- Publican
- Joe’s Stone Crab: It’s a steakhouse and it’s exhausting to get into at night time, however should you go for boozy brunch it’s nice.
- Parson’s Rooster & Fish: Not likely brunch however only a nice people-watching patio.
- Huge Star: Chicago basic taco joint with extremely wanted patio
- 3 Arts Membership
Dinner
- Bavette’s Bar & Boeuf
- Large
- The Roister
- Avec
- Inexperienced Road Smoked Meats: A terrific BBQ joint and Excessive 5 Ramen is under.
- RPM Steak
- Boeufhaus
- Maple & Ash
- Nico Osteri
Drinks
- Billy Sunday
- Aviary (attempt to get all the way down to the workplace)
- Violet Hour
- Begin at Scofflaw and work your means over to Greatest Intentions
- Longman & Eagle
- The California Clipper: Been round since earlier than prohibition!
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