All itineraries
Chicago, Illinois, United States
1 week in Chicago
Architecture, deep-dish and a lakefront skyline. Here's how to spend 1 week in Chicago: a realistic day-by-day plan you can copy and tweak. The best time for this 1 week Chicago trip is June, July and August. Budget roughly $150/person/day before flights.
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Length
1 week
Best time
June, July, August
~Cost/day
$150
Currency
USD
Make this trip yours
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Your 1 week Chicago itinerary, day by day
1
Day 1
09:00
Fisk Generating Station~$5
The Fisk Generating Station, also known as Fisk Street Generating Station or Fisk Station, is an inactive medium-size, coal-fired electric generating station located at 1111 West C
12:30
Palmisano Park
Henry C. Palmisano Park, or Palmisano Park is a 26.60-acre community park in the Bridgeport neighborhood of Chicago, Illinois. The park was first opened in 2009 as Stearns Quarry P
16:00
Canal Street railroad bridge
The Canal Street railroad bridge is a vertical-lift bridge across the south branch of the Chicago River in Chicago, Illinois. It was designated a Chicago Landmark on December 12, 2
2
Day 2
09:00
Halsted station (CTA Orange Line)~$5
Halsted station is an "L" station on the CTA Orange Line, located near the intersection of Halsted Street and Archer Avenue in the Bridgeport neighborhood of Chicago. The station o
12:30
Pilsen Historic District~$5
The Pilsen Historic District is located in the Lower West Side community area of Chicago and is among the few neighborhoods with buildings that survived the Great Chicago Fire of 1
16:00
Cermak Road Bridge Historic District~$5
The Cermak Road Bridge Historic District is a national historic district in the Lower West Side neighborhood of Chicago, Illinois. The district includes the Cermak Road Bridge, whi
3
Day 3
09:00
Zion Evangelical Lutheran Church (Chicago)
Zion Evangelical Lutheran Church was a church in Chicago on 19th and Peoria streets in the Pilsen neighborhood. The church was founded in 1850 and the current remains of the church
12:30
St. Barbara Church (Chicago)
St. Barbara's in Chicago - historic church of the Roman Catholic Archdiocese of Chicago located in Chicago, Illinois, at 2859 South Throop St.
16:00
Thalia Hall (Chicago)~$5
Thalia Hall is a historic building in Pilsen, Chicago, which is a mixed-use music, retail, and bar/restaurant space. It was designated as a Chicago Landmark on October 25, 1989.
4
Day 4
09:00
The Duck Inn~$5
The Duck Inn is a restaurant in Chicago, Illinois. It was a semifinalist in the Outstanding Restaurant category of the James Beard Foundation Awards in 2024.
12:30
Dusek's Board & Beer~$5
Dusek's was a restaurant in Chicago, Illinois. The gastropub served American cuisine.
16:00
Halsted Street station~$5
Halsted Street, also known as Halsted Street/UIC, is a station on Metra's BNSF Line, located in Chicago, Illinois. The station is 1.8 miles (2.9 km) away from Union Station, the ea
5
Day 5
09:00
Alton Junction~$5
The Alton Junction, more commonly known as the 21st Street Crossing, is a historically significant rail location in Chicago, Illinois. The junction can be found just east of Canal
12:30
Schoenhofen Brewery Historic District~$5
The Schoenhofen Brewery Historic District is centered on the former site of the Peter Schoenhofen Brewing Company at 18th and Canalport Avenue in the Pilsen neighborhood of Chicago
16:00
South Water Market~$10
South Water Market is a historic produce market in the Lower West Side neighborhood of Chicago, Illinois. Completed in 1925, the complex was designed as a structured replacement to
6
Day 6
09:00
Benito Juarez Community Academy~$5
Benito Juarez Community Academy, commonly known as Juarez High School and abbreviated as BJCA, is a public four-year high school in the Pilsen neighborhood on the west side of Chic
12:30
South Water Market~$10
South Water Market is a historic produce market in the Lower West Side neighborhood of Chicago, Illinois. Completed in 1925, the complex was designed as a structured replacement to
16:00
Halsted station (CTA Orange Line)~$5
Halsted station is an "L" station on the CTA Orange Line, located near the intersection of Halsted Street and Archer Avenue in the Bridgeport neighborhood of Chicago. The station o
7
Day 7
09:00
Palmisano Park
Henry C. Palmisano Park, or Palmisano Park is a 26.60-acre community park in the Bridgeport neighborhood of Chicago, Illinois. The park was first opened in 2009 as Stearns Quarry P
12:30
Canal Street railroad bridge
The Canal Street railroad bridge is a vertical-lift bridge across the south branch of the Chicago River in Chicago, Illinois. It was designated a Chicago Landmark on December 12, 2
16:00
Zion Evangelical Lutheran Church (Chicago)
Zion Evangelical Lutheran Church was a church in Chicago on 19th and Peoria streets in the Pilsen neighborhood. The church was founded in 1850 and the current remains of the church
A starting point, not a script. Reshuffle it in the planner →
What 1 week in Chicago costs
What this trip costs
$1,674
Flights$45027%
Stay$40524%
Activities$18911%
Food$31519%
Local transport$1268%
Shopping$845%
Buffer$1056%
$239/day
Estimates for planning, so check live prices before you book.
Have more or less time in Chicago?
1 week in Chicago: FAQ
Is 1 week enough for Chicago?+
1 week is a comfortable amount of time to explore Chicago, with room for day trips and a slower pace. The plan above balances the must-sees with time to wander.
What should I do on day 1 in Chicago?+
Start with Fisk Generating Station, Palmisano Park and Canal Street railroad bridge. The full first day is mapped out above.
How much does 1 week in Chicago cost?+
Budget around $150 per person per day for a mid-range trip (stay, food and activities), before flights, so roughly $1,050 per person for 1 week. The cost breakdown above splits it by category.
When is the best time to visit Chicago?+
The best months to visit Chicago are June, July, August and September, when the weather suits sightseeing best.