Land at O’Hare, UA 1710
ORD Terminal 1
Allow the full 30 minutes to deplane and walk down to the Blue Line.
Thu 20Land, river, blues
16:59 to 21:15
Blue Line45 minORD to Clark/Lake
Boarding the train around 5:30. Two-minute walk to the hotel at the other end.
Check in, drop bags
1 W Upper Wacker Dr
Confirmation 72536317
Walk3 minHotel to Riverwalk
River walk, heading west
Wacker at Dearborn
Down to the Riverwalk, then west along the south bank to Franklin where it ends. Carry on to Wolf Point, where the three branches meet. About 25 minutes at a slow pace.
Lyft15 min$18 to $25Wolf Point to Sapori
Dinner: Sapori Trattoria
2701 N Halsted St
Fifteen-minute grace period, then the table goes. Kitchen closes at 9.
BookedOpenTable 2110225001 · Table for 2
Walk4 minSapori to Kingston Mines
Kingston Mines
2548 N Halsted St
$15 cover. Two rooms alternating. The sets worth staying for start around 9:30.
Lyft15 min$20 to $30Kingston Mines to hotel
The Brown Line stops running around 1 AM.
Back at the hotel
Fri 21Little Italy, Bridgeport, Rate Field
09:00 to 18:00
Walk10 minHotel to Millennium Park
Millennium Park and the Cultural Center
78 E Washington St
The Cultural Center opens at 10. The Tiffany dome is on the third floor and it is free.
Lyft15 min$16Loop to Little Italy
Ask for 1438 W Taylor, the west end of the strip.
Little Italy on foot
Taylor Street
Little Italy on foot · 11:35 to 14:15
A straight walk east along Taylor Street, about a mile end to end with stops. Taylor is what is left of the neighborhood after the Eisenhower Expressway and the UIC campus cut through it in the 1950s and 60s, which is part of what makes the surviving stretch worth walking.
Conte Di Savoia · 1438 W Taylor
Old-line Italian grocer and deli. Go in for the smell of it even if you buy nothing.
National Italian American Sports Hall of Fame · 1431 W Taylor
Small, odd, free to look at from the plaza where the Joe DiMaggio statue stands.
Arrigo Park · one block south at Loomis
Shaded, quiet, good for ten minutes.
Al’s #1 Italian Beef · 1079 W Taylor
Around 12:30. The 1938 original. Dipped, hot and sweet peppers.
Mario’s Italian Lemonade · 1068 W Taylor
Directly across. Open until 11 PM in August, cash only. The actual reason to be on Taylor Street in summer. Lemon or watermelon for the traditional answer.
Jane Addams Hull-House Museum · 800 S Halsted
Twelve-minute walk from Al’s. Free, open Friday until 4:50, the last surviving building of the settlement house that shaped a century of American social policy. Reserve a free slot online in advance. Worth 45 minutes.
Lyft15 min$16Hull-House to Bridgeport
No clean El connection here.
Bridgeport on foot
2700 S Halsted St
Bridgeport on foot · 14:40 to 17:45
One walk south down Halsted, about a mile and a quarter.
Palmisano Park · 2700 S Halsted
2:40 to 3:40. A limestone quarry, then a landfill, now a park with a fishing pond in the pit. Climb the mound at the south end for the skyline view nobody puts on a postcard.
South on Halsted
3:40 to 4:20. Bridgeport produced five Chicago mayors. Richard J. Daley’s bungalow still stands at 3536 S Lowe, two blocks west of Halsted at 35th, startlingly modest for a man who ran the city for 21 years.
Ramova Theatre · 3520 S Halsted
4:20 to 5:30. A 1929 movie palace that sat dark for 38 years and reopened in 2024 with a taproom and grill. Open Friday from 4. Have a beer under the fake Spanish courtyard ceiling.
West to the ballpark
5:30 to 5:50. About 0.8 miles along 35th.
SwapMaria’s Packaged Goods and Community Bar, 960 W 31st, a liquor store with a bar behind it and Kimski, a Polish-Korean kitchen, attached. Opens Friday at 3. It is off the Halsted walking line, so treat it as a swap rather than an addition.
Walk20 minRamova to Rate Field
The tour ends at the ballpark: 0.8 miles west along 35th.
White Sox vs Mets, Rate Field
333 W 35th St
First pitch 6:40.
Red Line15 minRate Field to hotel
Sox/35th to Lake. Faster than any car leaving that lot.
Back at the hotel
Sat 22Lula first, the 606 back, museum by noon
09:10 to 20:15
Blue Line20 minHotel to Logan Square
Leave at 8:35. Then a six-minute walk.
Lula Cafe
2537 N Kedzie Blvd
Walk in and put your name down. Service runs 9 to 3. The breakfast burrito is the thing people order.
Walk-in only. Lula takes no brunch reservations at all. Standing advice is to arrive before 10 on a weekend.
Walk4 minLula to the 606
The 606 / Bloomingdale Trail, walking east
Kedzie ramp
Kedzie to Damen is 2.2 miles, roughly 50 minutes at a steady pace.
Blue Line14 minDamen to Monroe
Then 8 min walk east to Michigan.
Art Institute of Chicago
111 S Michigan Ave
Opens at 11, closes at 5. Enter through the Modern Wing on Monroe. Five hours is enough for three wings if you are disciplined.
Walk10 minArt Institute to hotel
Back to the hotel to change
Red Line22 minHotel to Wilson
Lake to Wilson, then 3 min north on Broadway.
Dinner: Demera
4801 N Broadway
Ethiopian.
BookedResy, 2 guests, dining room
Walk1 minDemera to Green Mill
The Green Mill
4802 N Broadway
Directly across the intersection. Cash only, plus a cover.
Red Line22 minGreen Mill to hotel
Red Line runs 24 hours. Lyft is about $28.
Back at the hotel
Sun 23Calumet Fisheries, then family
10:05 to 17:30
Lyft30 min$40 to $50Hotel to Calumet Fisheries
No reasonable rail route to the far southeast side on a Sunday.
Calumet Fisheries
3259 E 95th St
Opens at 10. Cash only, ATM inside. No indoor seating; you eat standing or at the picnic tables by the bridge. Order the smoked salmon and the smoked trout. Fried is good, smoked is the reason to come. The bridge overhead is the one the Bluesmobile jumps in The Blues Brothers.
Lyft30 minCalumet Fisheries to hotel
Bonnie with family
Korean spa and a meal.
Walk12 minHotel to Zarella
Dinner: Zarella Pizzeria & Taverna
Conditional531 N Wells St
Tavern-style. Twelve-minute walk north across the river. Conditional on the afternoon.
Mon 24Breakfast, then out
08:15 to 14:30
Breakfast: Pittsfield Cafe
55 E Washington St
Opens at 7. An old-school counter-and-booth diner in the lobby atrium of the 1927 Pittsfield Building: 38 storeys of Art Deco with a gilded five-storey interior court. Egg and cheese on a croissant, house-made corned beef hash, and a room most visitors never see.
Lou Mitchell’s on Jackson is the answer everyone gives, and it is the right one, except that it is closed Mondays and Tuesdays. If you want a bigger room and a park view instead, Eggy’s Diner at 333 E Benton opens at 7:30 and is a 12-minute walk.
Walk8 minPittsfield to hotel
Check out
Depart for O’Hare
Clark/Lake
Blue Line45 minClark/Lake to ORD
At the terminal around 11:50, gate by 12:20.
UA 587 to Washington
ORD
Bookings
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Practical
- Hotel
- Renaissance Chicago Downtown
1 W Upper Wacker Dr, Chicago, IL 60601
Confirmation 72536317 - Flights
- UA 1710 · SAN to ORD · arrives Thu 20 Aug, 16:59
UA 587 · ORD to DCA · departs Mon 24 Aug, 14:30 - Cash
- Three cash-only stops: Calumet Fisheries, Mario’s Italian Lemonade, and the Green Mill. Kingston Mines takes $15 at the door. Carry at least $150 in bills.
- The Monday conflict
- A client call sits at 2:00 to 2:30 PM Central, inside the boarding window for UA 587. The full note is under Monday.