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HomeMillennial TravelFinal 3 Days in Chicago + Maps!

Final 3 Days in Chicago + Maps!

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I first visited Chicago all the way in which again in 2010 and my recollection of town had develop into considerably hazy so I made a decision it was excessive time I am going again. This time I returned to The Windy Metropolis with the only function of penning this detailed weekend itinerary so I hope you discover it helpful!

Having visited town in each summer season and winter I’d counsel visiting in summer season for those who can. Winter is simply brutal and with that wind, it makes it troublesome to stroll round for too lengthy. Summertime brings hotter climate, which implies you’ll be able to see and achieve this way more.

This 3-day Chicago itinerary covers all the highest points of interest, together with Cloud Gate, Skydeck Chicago, Magnificent Mile, Lincoln Park and extra. Chicago has tons of museums you’ll be able to go to, together with observatories, parks and even seashores. 

After all, in your weekend in Chicago I’m certain you’ll need to do numerous consuming and consuming (and maybe pattern some Chicago sizzling canine and deep dish pizza) so I’ve added in among the finest locations to eat and drink too. 

Chicago Theater Chicago

Weekend in Chicago Itinerary Overview

Right here’s a fast overview of the way you’ll spend your weekend in Chicago:

  • Day 1: Chicago RiverWalk, Millennium Park, Cloud Gate, Artwork Institute of Chicago, Skydeck Chicago.
  • Day  2: Lincoln Park, Magnificent Mile, Starbucks Reserve, Museum of Modern Artwork, John Hancock Constructing. 
  • Day 3: Navy Pier, Discipline Museum, Shedd Aquarium, elective Wrigley Discipline.

Be sure you put on comfortable strolling sneakers since you’ll be doing a good bit of strolling.

Day 1: Chicago RiverWalk, Millennium Park, Cloud Gate, Artwork Institute of Chicago, Skydeck Chicago

Goddess and the Baker

Kick-off your weekend in Chicago with breakfast at Goddess and the Baker, Riverfront. Goddess and the Baker has just a few completely different areas all through town, however the riverfront location makes essentially the most sense for this itinerary. 

On the menu you’ll discover a big number of breakfast objects, together with omelets, shakshuka, bagels, avocado toast and /I’m burritos. In addition they supply a big number of coffees and drinks, together with a shiny Glitter Gold Latte! The setting is funky and funky, with an enormous signal that claims “Eat Now, Caffeinate”.

Chicago Riverwalk

Chicago Riverwalk

When you’ve lined your abdomen, stroll alongside the Chicago Riverwalk, which is a scenic walkway alongside the south financial institution of the Chicago River. Right here you’ll be able to snap unimaginable images of the river and Chicago’s skyscrapers.

The 1.25-mile lengthy path consists of 4 distinct districts; The Confluence, The Arcade, The Civic, and the Esplanade. It additionally options a wide range of public artwork works together with murals, sculptures, and banners. 

Essentially the most well-known work is Artwork on theMART, which is the most important video-projection artwork set up on the planet. At 7:30 & 8:00PM day-after-day, up to date artwork work is projected onto the two.5 acre façade of theMART constructing.

Millennium Park & Cloud Gate

The Bean, Cloud Gate Chicago

After strolling alongside the riverfront, it’s time to make a proper on N Stetson Ave or N Columbus Dr and head all the way down to Millennium Park. A serious spotlight of the park is Cloud Gate, which you’ve most likely seen in numerous images of Chicago! Individuals additionally discuss with it as “The Bean” as a result of it’s mainly an enormous sculpture formed like a bean. 

Cloud Gate is likely one of the most well-known sights in Chicago and its mirrored floor displays the Chicago skyline and surrounding park. You’ll normally see a whole bunch of individuals gathered round it taking images of their distorted reflections. 

Unveiled in 2004, the sculpture was created by artist Anish Kapoor and measures 33 ft excessive, 42 ft large, and 66 ft lengthy. The shiny exterior was impressed by liquid mercury and is constituted of 168 large chrome steel plates, which have been welded collectively for a seamless end. Contained in the construction are two giant metallic rings which can be linked through a truss framework.

Crown Fountain Chicago

My different favourite spotlight of the park is Crown Fountain, which is a big LED sculpture with a fountain. Designed by Spanish artist Jaume Plensa, it consists of two 50-foot glass block towers positioned at every finish of a shallow reflecting pool. 

The towers show the faces of Chicago residents, who’ve water flowing out of their mouths via an outlet within the display. Youngsters like to play right here on sizzling summer season days.

Artwork Institute of Chicago

Art Institute of Chicago

Hold strolling a bit additional and also you’ll come to the Artwork Institute of Chicago, which was based in 1879 is likely one of the oldest and largest artwork museums on the planet. The principle assortment options masterpieces from the likes of Van Gough, Monet, Picasso, Matisse, Renoir and Seurat. 

Remember it’s closed on each Tuesdays and Wednesdays, so don’t attempt to go to on both of as of late! 

The Artwork Institute is included within the Chicago CityPASS for those who resolve to buy one. Or you’ll be able to click on right here to view pricing and purchase tickets. 

Revival Meals Corridor & Skydeck Chicago

HERO Coffee Roasters Chicago

For those who like espresso, stroll alongside E Jackson Boulevard to HERO Espresso Roasters, which is a tiny espresso store positioned down the top of a slender alleyway. There’s a lit up signal that claims “Espresso” and is a superb spot for Instagram-worthy images. Whereas I can’t vouch for the espresso as I’m not a espresso drinker, I did attempt their sizzling chocolate! 

Subsequent up make your technique to W Adams Avenue and Calder’s Flamingo, which is a 53-foot (16 m) metal sculpture created by artist Alexander Calder. The sculpture is painted brilliant purple to distinction towards town’s skyscrapers. 

Hold strolling west alongside W Adams Avenue and also you’ll finally end up at Revival Meals Corridor, which is a cute meals corridor with a espresso store and numerous meals stalls serving all the pieces from poke to empanadas. 

For those who’re feeling peckish, I like to recommend attempting Artwork of Dosa, which is an off-the-cuff idea celebrating the South Indian delicacy—the masala dosa. The dosa is mainly a skinny crispy pancake that’s been rolled up and full of yummy fillings flavored with Indian spices. 

View of Chicago from Skydeck Chicago

All the way in which on the finish of W Adams Streetreach you’ll uncover Skydeck Chicago, which is positioned on the 103rd flooring of the Willis Tower. That is one statement deck you undoubtedly don’t need to miss! Whereas the view is wonderful, the spotlight for me is definitely the interactive shows that information you thru the historical past of Chicago. You’ll uncover how the Willis Tower was constructed and be taught all about Chicago’s tradition. 

In a single part guests can stroll via a mockup of an L practice, which is definitely standing nonetheless however has video screens within the home windows to undertaking photos of shifting surroundings. 

Giant Hot Dog at Skydeck Chicago

There’s additionally an exhibition devoted to Chicago meals, which has a sculpture of an enormous sizzling canine and a slice of deep dish pizza. Actually there are many picture alternatives all through the Skydeck expertise, together with an enormous ‘Chicago’ signal and naturally, the Ledge.  

The Ledge Skydeck Chicago

When you get to the Skydeck you’ll be able to stand in clear bins that make you are feeling such as you’re suspended over town. From right here you’ll be able to take pleasure in breathtaking views over Chicago and throughout 4 completely different states!

To avoid wasting you having to line up for tickets, I’d counsel shopping for your tickets on-line earlier than you go or buying the CityPASS for those who plan on seeing numerous points of interest throughout your journey. Tickets price $30-$39 for adults and $22-33 for kids aged 3-11. 

The very best time to go to is both simply after opening or at sundown if you wish to get the very best footage! The Willis Tower additionally has numerous consuming and consuming choices, together with a sushi restaurant referred to as Sushi San. 

Dinner Time

Phew! That’s a whole lot of strolling. By this level you’ll most likely be feeling drained, so head again to your resort to calm down for a bit and clean up. 

When you’ve got time earlier than sundown then you can take a look at considered one of Chicago’s finest rooftop bars for views of town. Strive Cindy’s Rooftop, Cerise Rooftop, RAISED or LH Rooftop. 

For dinner you can take a look at both Venteux Brasserie or Fisk + Co. 

Venteux Brasserie is a big, dimly lit French restaurant serving oysters, steak frites, steak tartare, onion soup, mussels and different French dishes. 

Fisk + Co is simply not far away and serves fish and seafood. Gadgets on the menu embody clam chowder, Belgian mussels, shrimp cocktail, lobster roll and roasted salmon.

Day 2: Lincoln Park, Miracle Mile, John Hancock Constructing

Breakfast at La Fournette

On day 2, head to Lincoln Park, which is Chicago’s largest park, protecting an space of greater than 1,200 acres. However earlier than that, seize breakfast from La Fournette – a cute French bakery not removed from the park entrance. The bakery sells all types of yummy pastries in addition to French classics reminiscent of Croque Madame and Quiche Lorraine. You may dine on the restaurant or take it to go and luxuriate in breakfast within the park. 

Lincoln Park Conservatory

Lincoln Park Conservatory

Throughout the park you’ll be able to go to the well-known Lincoln Park Zoo, which is free to enter. Personally I’ve made the choice to not go to any extra zoos. I discover them miserable and don’t like seeing animals in captivity with everybody staring and pointing at them. 

Lincoln Park Conservatory

So go to the zoo if you want, however I a lot desire the Lincoln Park Conservatory, which was constructed between 1890 and 1895, changing a small greenhouse that existed there from the 1870s. This can be a lovely glass conservatory and botanical backyard that’s full of all forms of natural world. You may see all types of tropical palms, ferns, unique crops and orchids.

Lunch at Summer season Home Santa Monica

While you’re carried out with the park, head on over to Summer season Home Santa Monica, which is likely one of the most Instagrammable eating places in Chicago. You may stroll there from the park (takes about 20 minutes) or take an Uber. 

Summer season Home Santa Monica is a light-filled restaurant that includes a courtyard patio with a retractable glass ceiling. It looks like summer season all 12 months spherical on this restaurant, even in the midst of winter. I ordered the ahi tuna tartare and the hibiscus agua fresca – each have been nice! Positively ensure you go to for cocktails and meals in your weekend in Chicago. 

Magnificent Mile

Magnificent Mile Chicago

After Summer season Home, take the practice or Uber to Magnificent Mile, which is Chicago’s well-known purchasing avenue. Lining the highway you’ll see tons of designer retailers, together with Louis Vuitton, Boss and Burberry, plus many excessive avenue manufacturers. 

On the south finish of Magnificent Mile you’ll discover the Wrigley Constructing, which was impressed by the Seville Cathedral’s Giralda Tower in Spain and is considered one of Chicago’s most iconic architectural masterpieces. 

Wrigley Building

This landmark constructing was as soon as the corporate headquarters of Chewing gum magnate William Wrigley Jr. and has a really fascinating form. It consists of two towers which can be linked by a third-floor bridge and from sure angles the constructing seems to be fully flat. The dazzling white towers illuminate town 

Starbucks Reserve

Clacker Board at Chicago Roastery

A spotlight of Magnificent Mile is the Starbucks Reserve Chicago Roastery, which opened in 2019. I’m not even a giant Starbucks fan however I assumed this was actually spectacular. Unfold over a number of flooring on Magnificent Mile, Chicago Roastery . 

While you stroll via the doorways of Chicago Roastery you’ll immediately discover the clacker board, which shows information on what Starbucks is roasting that day in addition to any particular occasions that is perhaps developing. On this flooring you’ll be able to see the espresso being roasted and have your picture taken with the ‘Chicago Wall’, which is constituted of Starbucks Reserve espresso playing cards. 

Starbucks Reserve Chicago Roastery

As you experience the spiral escalator at Starbucks Reserve you’ll discover the futuristic-looking ‘Cask’. This 56-foot tall centerpiece acts like an hourglass with roasted beans because the grains of sand.  On the second flooring you’ll discover an genuine Italian bakery created by Rocco Princi, which serves numerous flatbreads and refreshing drinks.

Experiental Coffee Bar at Chicago Roastery

The third flooring is all in regards to the artwork and science of creating espresso. Right here you’ll be able to sit down on the Experiental Espresso Bar to pattern espresso flights and witness exploratory brewing strategies. 

For those who fancy one thing a bit stronger, the fourth flooring is the place you’ll be able to order cocktails and different alcoholic drinks. The Arriviamo Cocktail bar gives progressive espresso and tea-based cocktails designed by native Chicago mixologists. 

Museum of Modern Artwork

Museum of Contemporary Art Chicago

Situated east of Magnificent Mile, The Museum of Modern Artwork is likely one of the world’s largest up to date artwork museums. Guests can view the everlasting assortment, which incorporates greater than 2,500 artwork works from 1920 to the current day, in addition to rotating short-term artwork exhibitions. 

The museum is open every day besides Mondays. Opening hours are 10am-5pm Wednesday to Sunday and 10am-9pm on Tuesdays. 

The Signature Lounge

As a substitute of paying the admission charge for 360 Chicago observatory, seize a cocktail at The Signature Lounge on the 96th flooring of 875 North Michigan Ave, previously the John Hancock Middle. Attempt to go to round sundown time on a transparent day for the very best views! 


Sushi San Chicago

For dinner, head to Sushi-san, which is a vigorous sushi spot with an extended sushi bar and an old-school hip-hop soundtrack. The menu encompasses a number of appetizers, maki and sushi units, plus charcoal grilled meats and greens. For dessert attempt the Japanese Breakfast (fluffy pancakes with matcha butter and black sugar) or the Emochi (emoji formed Japanese mochi). 

For those who’re not feeling sushi, you can additionally seize some Italian meals at Eataly, which is an Italian market and meals corridor with a number of Italian eateries to select from. There are a number of Eataly shops all through the U.S, so for those who’ve been to 1 earlier than, you’ll already know the idea. 

Day 3: Navy Pier, Discipline Museum, Shedd Aquarium, Non-compulsory Wrigley Discipline

Navy Pier

Navy Pier ferris wheel, Chicago

On the ultimate day of your lengthy weekend in Chicago make your technique to Navy Pier, which is an iconic pier on the shoreline of Lake Michigan. The pier attracts thousands and thousands of tourists annually and is a significant leisure heart, with all types of outlets, eating places and rides. Take a experience on the Centennial Wheel, which gives unparalleled views of the Chicago skyline and Lake Michigan. 

Discipline Museum & Shedd Aquarium

Field Museum Chicago

Afterwards you may have tons of museums to select from. The Discipline Museum is Chicago’s pure historical past museum. In the principle corridor stands a 28-ft tall solid of a titanosaur that lived thousands and thousands of years in the past in Argentina. It’s the largest dinosaur ever found by scientists and it weighed about 70 tons in actual life!  

Close by is the Shedd Aquarium, one of many largest aquariums on the planet. Exhibitions function a wide selection of aquatic life together with sharks, sea otters, turtles, seahorses, penguins, saltwater fish, stingrays, sea lions and beluga whales.

Wrigley Discipline

Wrigley Field Chicago

When you’ve got extra time, you can additionally head north to Wrigley Discipline, which has been the house of the Chicago Cubs baseball crew for over a century. Guided excursions final 75-90 minutes and supply a behind-the-scenes have a look at this iconic stadium. 

On non-game days guests can see the seating bowl, press field, Budweiser bleachers, outfield ivy, customer’s clubhouse, Cubs’ dugout and the sphere. To get there, both hop in an Uber or catch the CTA Crimson Line, which can take you to Addison Station proper by the stadium.

Giordano's - Chicago's Famous Stuffed Pizza sign

For dinner, take a look at River Roast, or for those who fancy attempting deep dish pizza, head to Giordano’s. Giordano’s has been serving Chicago’s legendary pizza since 1974 and there are a number of areas all through town.

Attending to Chicago

Chicago Skyline

Chicago has two essential airports – O’Hare Worldwide Airport and Chicago Halfway Worldwide Airport. For flights, examine Google Flights, Kayak and Skyscanner. 

The town is a significant hub for each United Airways and American Airways however many home airways fly there, together with Frontier, Spirit, JetBlue and Delta Air Strains. 

From each airports it’s tremendous straightforward to get downtown by public transportation. The Chicago Transit Authority (CTA) Blue Line ‘L’ Prepare connects on to O’Hare, whereas the CTA Orange Line ‘L’ Prepare connects on to Halfway.

For those who don’t need to fly, you can get there by practice, bus or automobile. Bus firms that serve Chicago embody, Greyhound and Complete Constitution Bus Chicago. 

Chicago’s essential practice station is named Union Station and serves each Amtrak and Metra, town’s commuter rail service.

Getting Round Chicago

Chicago CTA Train from Chicago Midway

Getting round Chicago is tremendous straightforward and each airports have public transportation to take you into town, so there’s actually no want for a automobile. For longer distances between points of interest I’d counsel taking an Uber however in any other case you should use the CTA ‘L’ Prepare which can take you most locations. 

To pay, you should use contactless (e.g Apple Pay or contactless debit/bank card) or buy Ventra tickets on the machines within the station. Try the present fares right here on the CTA web site. For those who plan to take a couple of experience on the CTA, finest to get a day move because it’s significantly better worth than getting single tickets. 

The place to Keep On Your Weekend in Chicago

I stayed on the Westin Chicago throughout my final journey. Previous to that I stayed at Chicago Getaway Hostel. For those who’re simply spending a weekend in Chicago then I’d suggest staying someplace within the downtown space near the river so you may have easy accessibility to all the highest points of interest. Listed here are some lodging choices:


The Westin Chicago

Westin Chicago River North – Located within the River North neighborhood within the coronary heart of downtown, Westin Chicago boasts a wonderful location near all the principle points of interest. It’s a stable possibility in your weekend in Chicago and after a day of sightseeing, you’ll be able to calm down and luxuriate in drinks in 320 RiverBar, which is positioned within the foyer stage of the constructing. 

Thompson Chicago – A superb luxurious possibility, Thompson Chicago is a hip, boutique resort positioned only a quick stroll from Oak Avenue Seashore and the shores of Lake Michigan. Interiors are accented with loads of velvet, leather-based and heat American woods to present a luxurious, luxurious really feel.

Pendry Chicago – Housed inside the iconic 1929 Artwork Deco Carbide & Carbon Constructing in Chicago’s Loop neighborhood, Pendry Chicago is a up to date resort with 364 visitor rooms and suites. The resort is residence to a state-of-the-art health heart and an al fresco rooftop area with skyline views. There’s additionally a French restaurant referred to as Venteux and an intimate resort bar serving Sunday afternoon boozy tea. 

The Guesthouse Lodge – The Guesthouse Lodge gives one, two and three bed room suites full with full dimension kitchens, stress-free dwelling areas and personal balconies with gasoline grills. Pets are welcome and services embody a roof deck, a health heart and a clubroom with library.


Chicago Getaway Hostel – Situated within the Lincoln Park neighborhood of Chicago, Chicago Getaway Hostel gives free WiFi, a free espresso bar and weekly social occasions. This boutique hostel gives each non-public and shared rooms with both full, half or shared bogs.

HI Chicago Hostel – Located in Chicago’s Loop neighborhood, HI Chicago Hostel boasts a central location inside strolling distance of Millennium Park, the Bean and town’s different high points of interest. There’s an on-site café, a recreation room, free WiFi and a totally stocked visitor kitchen. 

Freehand Chicago – Housed in a traditional 1927 constructing in Chicago’s  River North neighborhood, Freehand Chicago is a classy resort and hostel with a cool cocktail bar referred to as the Damaged Shaker. 

Wrigley Hostel – This hostel is simply steps from Wrigley discipline and has its personal outside lounge with BBQ for grilling on heat summer season nights. Company can take pleasure in free occasions and socialize within the frequent room, which encompasses a pool desk, ping pong desk, foosball, a BYOB bar, giant flat display TV and video games. 

Greatest Time to Go to Chicago

This one’s a no brainer. Go in summer season. Chicago in winter is freezing – so bitterly chilly that your fingers and face damage in the event that they’re uncovered. 

Whereas exploring town for the aim of making this itinerary I skilled each sort of climate – bitterly chilly winds, snow, torrential rain, patches of solar…you identify it. That was in March over a interval of simply three days. Sooner or later I used to be so chilly that I needed to cease each few ft to heat up inside a CVS pharmacy or a restaurant. 

So do your self a favor and plan your weekend in Chicago within the summertime when the climate is heat and sunny and you’ll discover the parks and even metropolis seashores. June-September are undoubtedly the very best months to plan your weekend in Chicago. 

A Remaining Phrase…

I hope you’ve discovered this Chicago itinerary helpful! With 3 days in Chicago you’ll be able to attempt a few of Chicago’s well-known eats and see many of the high museums and observatories. Go to in summer season for those who can, but when you must go in winter, ensure you deliver loads of layers and a puffy coat!

Different itineraries within the US:



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