Chicago, IL 2 Day Itinerary
The windy city, known for great food and incredible architecture, has so much to offer any visitor. This itinerary is completely walkable, with beautiful views all along the way.
24 Places • 3 Saves • ago
Free
Hotel Recommendations
Sofitel Chicago Magnificent Mile
@emilyworden
Great little neighborhood, just off of Michigan Ave and the lakeshore. Rooms are clean and spacious.
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Thompson Chicago, by Hyatt
@emilyworden
A luxury boutique hotel in a great location, just off of the lakeshore.
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Details
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Details
The Godfrey Hotel Chicago
@emilyworden
This consistently affordable hotel is a great budget-friendly find. Clean and modern rooms.
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Details
Food Recommendations
Hugo's Frog Bar & Fish House
@emilyworden
This is a sister restaurant to Gibson's Steakhouse next door, and home to the most incredible crab cake. While the Gibsons steaks are still on the menu, the fish and seafood options the specialty. Food and service are always top notch.
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Details
The Purple Pig Restaurant
@emilyworden
Known for small plates, this restaurant has a varied menu with Italian, Greek and Spanish influences. The fresh pasta is some of the best in the city.
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Details
Blue Door Kitchen & Garden
@emilyworden
This farm to table restaurant was created by executive chef and co-owner Art Smith, the former personal chef for Oprah. The food is consistently great, with charming decor and relaxing outdoor seating.
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Details
Lou Malnati's Pizzeria - Michigan Ave
@emilyworden
If you're wanting to try classic Chicago deep-dish pizza, this is the place for you. With several locations around the city, there is likely one close to wherever you are.
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Details
Wildberry Pancakes & Cafe
@emilyworden
Everything is good here, especially can't go wrong with the berry bliss pancakes and any of the skillets.
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Details
Bavette's Bar & Boeuf
@emilyworden
A classic steakhouse with a bit of a French flair. This restaurant is pricey but worth every penny. Great for a celebratory dinner as this place truly feels special. Reservations highly recommended.
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Details
Billy Goat Tavern (The Original)
@emilyworden
This recommendation is really more a fun place to see than a foodie destination. Around since 1934, the restaurant was featured in a classic SNL skit- "Cheezborger, cheezborger, cheezborger!" The menu has stayed fairly simple and affordable.
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Details
Garrett Popcorn Shops
@emilyworden
Try the Chicago mix, which is a combination of the caramel and the cheese popcorn. Locations all over the city
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Details
Day One
Start your Chicago trip with a river boat cruise, learning the history and architecture of the city. Spend some time exploring Millennium and Maggie Daley Park, finishing off the day with a sunset walk along the lakeshore.
Wendella Tours & Cruises
@emilyworden
Family owned and operated since 1935, a Wendella Architecture tour will take you along the Chicago river, sharing the rich history of the city.
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Details
Millennium Park
@emilyworden
With "The Bean" set to open in Spring 2024 after a refurbishment, this is a great spot particularly in the summer. Lots of concerts and special events take place here, so be sure to check out their calendar of events.
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Details
Maggie Daley Park
@emilyworden
Adjacent to Millennium Park, Maggie Daley has a number of fun activities and areas to enjoy.
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Details
Lakefront Trail
@emilyworden
The best skyline views are from the lake shore. You can get to this trail by taking an underpass from Michigan Avenue. A good place to start is the underpass near the gazebo by the Drake hotel.
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Details
Day Two
Option 1: Spend the day learning about natural history at the Field museum. (The Shedd Aquarium and Art Institute of Art are also great alternatives.) Next, enjoy the green space of Grant Park, or check out some shopping on Michigan Avenue. In the evening, take in one of the shows running in the theater district.
Field Museum
@emilyworden
From Egyptian mummies to SUE, the most complete Tyrannosaurus rex ever discovered, the Field museum is a great option for any natural history fans.
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Details
Grant Park
@emilyworden
Home to one of the largest fountains in the world, Buckingham Fountain. Each hour, a twenty minute water display reaches heights 150 feet in the air.
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Details
Michigan Avenue
@emilyworden
With shops lining the street, including tucked away malls, Michigan Avenue has you covered if shopping is your goal.
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Details
Broadway In Chicago
@emilyworden
With so many shows to choose from in the theater district, choose a show that best fits your group. They will not disappoint.
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Details
Option 2: A more budget friendly option with a neighborhood feel. Spend the day around Lincoln Park Conservatory and Zoo, followed by a night out at the Second City comedy club.
Lincoln Park Conservatory
@emilyworden
Built in 1877, the conservatory and surrounding gardens are free to enjoy but reservations are required.
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Details
Lincoln Park Zoo
@emilyworden
This zoo has been completely free since its opening in 1968. With over 200 different species, expansive gardens, and conservation efforts, this is well worth a visit.
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Details
The Second City
@emilyworden
This improv comedy club is where some of the most famous comedians got their start- Bill Murray, Dan Aykroyd, Steve Carell just to name a few. There is an age limit of 13 and up. Children between 13-17 must be accompanied by an adult.
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Details
* * *
CURATED BY
Hello, I'm Emily - hit hard by the Wanderlust bug, I devote all that I can to experiencing new adventures. In between trips, I spend my time researching and cultivating the perfect itineraries in order to optimize my vacation time. I want everyone to have the best trip possible so please feel free to check out my itineraries for inspiration and guidance. Happy traveling!
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Chicago, IL 2 Day Itinerary
The windy city, known for great food and incredible architecture, has so much to offer any visitor. This itinerary is completely walkable, with beautiful views all along the way.
24 Places • 3 Saves • ago
Free
Hotel Recommendations
Sofitel Chicago Magnificent Mile
@emilyworden
Great little neighborhood, just off of Michigan Ave and the lakeshore. Rooms are clean and spacious.
Add to
Details
Add to
Details
Thompson Chicago, by Hyatt
@emilyworden
A luxury boutique hotel in a great location, just off of the lakeshore.
Add to
Details
Add to
Details
The Godfrey Hotel Chicago
@emilyworden
This consistently affordable hotel is a great budget-friendly find. Clean and modern rooms.
Add to
Details
Food Recommendations
Hugo's Frog Bar & Fish House
@emilyworden
This is a sister restaurant to Gibson's Steakhouse next door, and home to the most incredible crab cake. While the Gibsons steaks are still on the menu, the fish and seafood options the specialty. Food and service are always top notch.
Add to
Details
The Purple Pig Restaurant
@emilyworden
Known for small plates, this restaurant has a varied menu with Italian, Greek and Spanish influences. The fresh pasta is some of the best in the city.
Add to
Details
Blue Door Kitchen & Garden
@emilyworden
This farm to table restaurant was created by executive chef and co-owner Art Smith, the former personal chef for Oprah. The food is consistently great, with charming decor and relaxing outdoor seating.
Add to
Details
Lou Malnati's Pizzeria - Michigan Ave
@emilyworden
If you're wanting to try classic Chicago deep-dish pizza, this is the place for you. With several locations around the city, there is likely one close to wherever you are.
Add to
Details
Wildberry Pancakes & Cafe
@emilyworden
Everything is good here, especially can't go wrong with the berry bliss pancakes and any of the skillets.
Add to
Details
Bavette's Bar & Boeuf
@emilyworden
A classic steakhouse with a bit of a French flair. This restaurant is pricey but worth every penny. Great for a celebratory dinner as this place truly feels special. Reservations highly recommended.
Add to
Details
Billy Goat Tavern (The Original)
@emilyworden
This recommendation is really more a fun place to see than a foodie destination. Around since 1934, the restaurant was featured in a classic SNL skit- "Cheezborger, cheezborger, cheezborger!" The menu has stayed fairly simple and affordable.
Add to
Details
Garrett Popcorn Shops
@emilyworden
Try the Chicago mix, which is a combination of the caramel and the cheese popcorn. Locations all over the city
Add to
Details
Day One
Start your Chicago trip with a river boat cruise, learning the history and architecture of the city. Spend some time exploring Millennium and Maggie Daley Park, finishing off the day with a sunset walk along the lakeshore.
Wendella Tours & Cruises
@emilyworden
Family owned and operated since 1935, a Wendella Architecture tour will take you along the Chicago river, sharing the rich history of the city.
Add to
Details
Millennium Park
@emilyworden
With "The Bean" set to open in Spring 2024 after a refurbishment, this is a great spot particularly in the summer. Lots of concerts and special events take place here, so be sure to check out their calendar of events.
Add to
Details
Maggie Daley Park
@emilyworden
Adjacent to Millennium Park, Maggie Daley has a number of fun activities and areas to enjoy.
Add to
Details
Lakefront Trail
@emilyworden
The best skyline views are from the lake shore. You can get to this trail by taking an underpass from Michigan Avenue. A good place to start is the underpass near the gazebo by the Drake hotel.
Add to
Details
Day Two
Option 1: Spend the day learning about natural history at the Field museum. (The Shedd Aquarium and Art Institute of Art are also great alternatives.) Next, enjoy the green space of Grant Park, or check out some shopping on Michigan Avenue. In the evening, take in one of the shows running in the theater district.
Field Museum
@emilyworden
From Egyptian mummies to SUE, the most complete Tyrannosaurus rex ever discovered, the Field museum is a great option for any natural history fans.
Add to
Details
Grant Park
@emilyworden
Home to one of the largest fountains in the world, Buckingham Fountain. Each hour, a twenty minute water display reaches heights 150 feet in the air.
Add to
Details
Michigan Avenue
@emilyworden
With shops lining the street, including tucked away malls, Michigan Avenue has you covered if shopping is your goal.
Add to
Details
Broadway In Chicago
@emilyworden
With so many shows to choose from in the theater district, choose a show that best fits your group. They will not disappoint.
Add to
Details
Option 2: A more budget friendly option with a neighborhood feel. Spend the day around Lincoln Park Conservatory and Zoo, followed by a night out at the Second City comedy club.
Lincoln Park Conservatory
@emilyworden
Built in 1877, the conservatory and surrounding gardens are free to enjoy but reservations are required.
Add to
Details
Lincoln Park Zoo
@emilyworden
This zoo has been completely free since its opening in 1968. With over 200 different species, expansive gardens, and conservation efforts, this is well worth a visit.
Add to
Details
The Second City
@emilyworden
This improv comedy club is where some of the most famous comedians got their start- Bill Murray, Dan Aykroyd, Steve Carell just to name a few. There is an age limit of 13 and up. Children between 13-17 must be accompanied by an adult.
Add to
Details
* * *
CURATED BY
Hello, I'm Emily - hit hard by the Wanderlust bug, I devote all that I can to experiencing new adventures. In between trips, I spend my time researching and cultivating the perfect itineraries in order to optimize my vacation time. I want everyone to have the best trip possible so please feel free to check out my itineraries for inspiration and guidance. Happy traveling!
PERSONALIZED TRAVEl SERVICES
Connect
with
a
local
expert
to
help
plan
your
ideal
trip
Send A Tip
Support Emily Worden’s work.
Select your tip amount
$5
$10
$20
$50
Or type in other amount