The Plan
Amtrak into Union Station Sun Mar 29 at 4:45 pm · Amtrak home from Union Station Thu Apr 9 at 3:05 pm. 10 full days. The Shamrock (Cicero) Mar 29–Apr 3, then River Hotel (Loop) Apr 3–Apr 9. Food suggestions reflect verified hours.
Sun · Mar 29
Arrival Day
🚂 ARRIVAL
Amtrak arrives Union Station · 4:45 pm. Head to The Shamrock in Cicero to check in, then explore or grab dinner.
Partly Cloudy · Breezy
↑ 47°F
↓ 31°F
🌅 7:10 am · 🌇 7:16 pm
Lake wind typical on arrival evening. Layer up.
Open today
· Firecakes Donuts - Lincoln Park · 6:30 am - 7:00 pm
· Firecakes Donuts - River North · 6:30 am - 9:00 pm
· Lou Mitchell's · 7:00 am - 2:00 pm
· Te'amo Boba - Chinatown · 11:00 am - 10:00 pm
· Te'amo Boba - River North · 12:00 pm - 9:30 pm
· Te'amo Boba - Water Tower Place · 12:00 pm - 6:00 pm
· Te'amo Boba Bar · 11:00 am - 8:00 pm
· Uni Uni Boba · 11:00 am - 11:30 pm
· McDonald's Walk-Up Window · 5:00 am - 12:00 am
· City Winery · 10:00 am - 10:00 pm
· Manny's Deli · 8:00 am - 3:30 pm
· Michael's Original Pizzeria & Tavern · 11:00 am - 10:00 pm
· Redhot Ranch · 10:30 am - 12:00 am
· Zaza's Pizzeria · 12:00 pm - 9:00 pm
Mon · Mar 30
Day 1 — Full Day
● FULL DAY
Mostly Cloudy · Windy
↑ 49°F
↓ 32°F
🌅 7:09 am · 🌇 7:16 pm
April averages around 15 mph wind — plan for it.
Open today
· Firecakes Donuts - Lincoln Park · 6:30 am - 5:00 pm
· Firecakes Donuts - River North · 6:30 am - 9:00 pm
· Te'amo Boba - Chinatown · 11:00 am - 10:00 pm
· Te'amo Boba - River North · 12:00 pm - 9:30 pm
· Te'amo Boba - Water Tower Place · 11:00 am - 7:00 pm
· Te'amo Boba Bar · 11:00 am - 8:00 pm
· Uni Uni Boba · 11:00 am - 10:00 pm
· McDonald's HQ Restaurant · 8:00 am - 5:00 pm
· McDonald's Walk-Up Window · 5:00 am - 12:00 am
· City Winery · 10:00 am - 10:00 pm
· Michael's Original Pizzeria & Tavern · 11:00 am - 11:00 pm
· Oasis Cafe · 10:30 am - 4:00 pm
· Redhot Ranch · 10:30 am - 12:00 am
Tue · Mar 31
Day 2 — Full Day
● FULL DAY
Variable Clouds · Breezy
↑ 50°F
↓ 33°F
🌅 7:09 am · 🌇 7:16 pm
Chance of light rain or leftover chill.
Open today
· Firecakes Donuts - Lincoln Park · 6:30 am - 5:00 pm
· Firecakes Donuts - River North · 6:30 am - 9:00 pm
· Te'amo Boba - Chinatown · 11:00 am - 10:00 pm
· Te'amo Boba - River North · 12:00 pm - 9:30 pm
· Te'amo Boba - Water Tower Place · 11:00 am - 7:00 pm
· Te'amo Boba Bar · 11:00 am - 8:00 pm
· Uni Uni Boba · 11:00 am - 10:00 pm
· McDonald's HQ Restaurant · 8:00 am - 5:00 pm
· McDonald's Walk-Up Window · 5:00 am - 12:00 am
· City Winery · 10:00 am - 10:00 pm
· Manny's Deli · 8:00 am - 7:30 pm
· Michael's Original Pizzeria & Tavern · 11:00 am - 11:00 pm
· Oasis Cafe · 10:30 am - 4:00 pm
· Redhot Ranch · 10:30 am - 12:00 am
· Zaza's Pizzeria · 4:00 pm - 9:00 pm
Wed · Apr 1
Day 3 — Full Day
● FULL DAY
Partly Cloudy · Chance of Rain
↑ 52°F
↓ 35°F
🌅 6:34 am · 🌇 7:15 pm
Average last snowfall date is Apr 1 — unlikely but possible.
Open today
· Firecakes Donuts - Lincoln Park · 6:30 am - 5:00 pm
· Firecakes Donuts - River North · 6:30 am - 9:00 pm
· Lou Mitchell's · 6:00 am - 2:00 pm
· Te'amo Boba - Chinatown · 11:00 am - 10:00 pm
· Te'amo Boba - River North · 12:00 pm - 9:30 pm
· Te'amo Boba - Water Tower Place · 11:00 am - 7:00 pm
· Te'amo Boba Bar · 11:00 am - 8:00 pm
· Uni Uni Boba · 11:00 am - 10:00 pm
· McDonald's HQ Restaurant · 8:00 am - 5:00 pm
· McDonald's Walk-Up Window · 5:00 am - 12:00 am
· City Winery · 10:00 am - 10:00 pm
· Manny's Deli · 8:00 am - 7:30 pm
· Michael's Original Pizzeria & Tavern · 11:00 am - 11:00 pm
· Oasis Cafe · 10:30 am - 4:00 pm
· Redhot Ranch · 10:30 am - 12:00 am
· Zaza's Pizzeria · 12:00 pm - 9:00 pm
Thu · Apr 2
Day 4 — Full Day
● FULL DAY
Partly Cloudy
↑ 53°F
↓ 36°F
🌅 6:32 am · 🌇 7:16 pm
Temps creeping up. Decent afternoon expected.
Open today
· Firecakes Donuts - Lincoln Park · 6:30 am - 7:00 pm
· Firecakes Donuts - River North · 6:30 am - 11:00 pm
· Lou Mitchell's · 6:00 am - 2:00 pm
· Te'amo Boba - Chinatown · 11:00 am - 10:00 pm
· Te'amo Boba - River North · 12:00 pm - 9:30 pm
· Te'amo Boba - Water Tower Place · 11:00 am - 7:00 pm
· Te'amo Boba Bar · 11:00 am - 8:00 pm
· Uni Uni Boba · 11:00 am - 10:00 pm
· McDonald's HQ Restaurant · 8:00 am - 5:00 pm
· McDonald's Walk-Up Window · 5:00 am - 12:00 am
· City Winery · 10:00 am - 10:00 pm
· Manny's Deli · 8:00 am - 7:30 pm
· Michael's Original Pizzeria & Tavern · 11:00 am - 11:00 pm
· Oasis Cafe · 10:30 am - 4:00 pm
· Redhot Ranch · 10:30 am - 12:00 am
· Zaza's Pizzeria · 12:00 pm - 9:00 pm
Fri · Apr 3
Day 5 — Hotel Changeover
● FULL DAY
Check out of The Shamrock by 11:00 am. Check in to River Hotel (75A E. Wacker Dr.) sometime this afternoon. Good day to explore Fulton Market or the West Loop — it's right by McDonald's HQ and Lou Mitchell's.
Mostly Sunny · Breezy
↑ 55°F
↓ 37°F
🌅 6:31 am · 🌇 7:17 pm
Hotel changeover day — good outdoor weather for the move.
Open today
· Firecakes Donuts - Lincoln Park · 6:30 am - 7:00 pm
· Firecakes Donuts - River North · 6:30 am - 11:00 pm
· Lou Mitchell's · 6:00 am - 2:00 pm
· Te'amo Boba - Chinatown · 11:00 am - 10:30 pm
· Te'amo Boba - River North · 12:00 pm - 9:30 pm
· Te'amo Boba - Water Tower Place · 11:00 am - 8:00 pm
· Te'amo Boba Bar · 11:00 am - 8:30 pm
· Uni Uni Boba · 11:00 am - 11:00 pm
· McDonald's HQ Restaurant · 8:00 am - 5:00 pm
· McDonald's Walk-Up Window · 5:00 am - 12:00 am
· City Winery · 10:00 am - 10:00 pm
· Manny's Deli · 8:00 am - 7:30 pm
· Michael's Original Pizzeria & Tavern · 11:00 am - 11:00 pm
· Oasis Cafe · 10:30 am - 4:00 pm
· Redhot Ranch · 10:30 am - 12:00 am
· Zaza's Pizzeria · 12:00 pm - 9:00 pm
Sat · Apr 4
Day 6 — Full Day
● FULL DAY
Partly Cloudy
↑ 56°F
↓ 38°F
🌅 6:29 am · 🌇 7:18 pm
Comfortable spring afternoon. Good for exploring.
Open today
· Firecakes Donuts - Lincoln Park · 6:30 am - 7:00 pm
· Firecakes Donuts - River North · 6:30 am - 11:00 pm
· Lou Mitchell's · 7:00 am - 2:00 pm
· Te'amo Boba - Chinatown · 11:00 am - 10:30 pm
· Te'amo Boba - River North · 12:00 pm - 10:00 pm
· Te'amo Boba - Water Tower Place · 11:00 am - 8:00 pm
· Te'amo Boba Bar · 11:00 am - 9:00 pm
· Uni Uni Boba · 11:00 am - 11:00 pm
· McDonald's Walk-Up Window · 5:00 am - 12:00 am
· City Winery · 10:00 am - 10:00 pm
· Manny's Deli · 8:00 am - 7:30 pm
· Michael's Original Pizzeria & Tavern · 11:00 am - 11:00 pm
· Oasis Cafe · 11:00 am - 3:00 pm
· Redhot Ranch · 10:30 am - 12:00 am
· Zaza's Pizzeria · 12:00 pm - 9:00 pm
Sun · Apr 5
Day 7 — Full Day
● FULL DAY
Mostly Sunny
↑ 58°F
↓ 39°F
🌅 6:27 am · 🌇 7:20 pm
One of the warmer days of the trip historically.
Open today
· Firecakes Donuts - Lincoln Park · 6:30 am - 7:00 pm
· Firecakes Donuts - River North · 6:30 am - 9:00 pm
· Lou Mitchell's · 7:00 am - 2:00 pm
· Te'amo Boba - Chinatown · 11:00 am - 10:00 pm
· Te'amo Boba - River North · 12:00 pm - 9:30 pm
· Te'amo Boba - Water Tower Place · 12:00 pm - 6:00 pm
· Te'amo Boba Bar · 11:00 am - 8:00 pm
· Uni Uni Boba · 11:00 am - 11:30 pm
· McDonald's Walk-Up Window · 5:00 am - 12:00 am
· City Winery · 10:00 am - 10:00 pm
· Manny's Deli · 8:00 am - 3:30 pm
· Michael's Original Pizzeria & Tavern · 11:00 am - 10:00 pm
· Redhot Ranch · 10:30 am - 12:00 am
· Zaza's Pizzeria · 12:00 pm - 9:00 pm
Mon · Apr 6
Day 8 — Full Day
● FULL DAY
Partly Cloudy · Breezy
↑ 57°F
↓ 38°F
🌅 6:26 am · 🌇 7:21 pm
Wind picks back up mid-trip. Jacket weather.
Open today
· Firecakes Donuts - Lincoln Park · 6:30 am - 5:00 pm
· Firecakes Donuts - River North · 6:30 am - 9:00 pm
· Te'amo Boba - Chinatown · 11:00 am - 10:00 pm
· Te'amo Boba - River North · 12:00 pm - 9:30 pm
· Te'amo Boba - Water Tower Place · 11:00 am - 7:00 pm
· Te'amo Boba Bar · 11:00 am - 8:00 pm
· Uni Uni Boba · 11:00 am - 10:00 pm
· McDonald's HQ Restaurant · 8:00 am - 5:00 pm
· McDonald's Walk-Up Window · 5:00 am - 12:00 am
· City Winery · 10:00 am - 10:00 pm
· Michael's Original Pizzeria & Tavern · 11:00 am - 11:00 pm
· Oasis Cafe · 10:30 am - 4:00 pm
· Redhot Ranch · 10:30 am - 12:00 am
Tue · Apr 7
Day 9 — Full Day
● FULL DAY
Cloudy · Chance of Rain
↑ 56°F
↓ 37°F
🌅 6:24 am · 🌇 7:22 pm
Spring showers more likely by early April.
Open today
· Firecakes Donuts - Lincoln Park · 6:30 am - 5:00 pm
· Firecakes Donuts - River North · 6:30 am - 9:00 pm
· Te'amo Boba - Chinatown · 11:00 am - 10:00 pm
· Te'amo Boba - River North · 12:00 pm - 9:30 pm
· Te'amo Boba - Water Tower Place · 11:00 am - 7:00 pm
· Te'amo Boba Bar · 11:00 am - 8:00 pm
· Uni Uni Boba · 11:00 am - 10:00 pm
· McDonald's HQ Restaurant · 8:00 am - 5:00 pm
· McDonald's Walk-Up Window · 5:00 am - 12:00 am
· City Winery · 10:00 am - 10:00 pm
· Manny's Deli · 8:00 am - 7:30 pm
· Michael's Original Pizzeria & Tavern · 11:00 am - 11:00 pm
· Oasis Cafe · 10:30 am - 4:00 pm
· Redhot Ranch · 10:30 am - 12:00 am
· Zaza's Pizzeria · 4:00 pm - 9:00 pm
Wed · Apr 8
Day 10 — Last Full Day
● FULL DAY
Last full day — make it count!
Partly Cloudy
↑ 58°F
↓ 38°F
🌅 6:22 am · 🌇 7:23 pm
Solid last full day weather on average.
Open today
· Firecakes Donuts - Lincoln Park · 6:30 am - 5:00 pm
· Firecakes Donuts - River North · 6:30 am - 9:00 pm
· Lou Mitchell's · 6:00 am - 2:00 pm
· Te'amo Boba - Chinatown · 11:00 am - 10:00 pm
· Te'amo Boba - River North · 12:00 pm - 9:30 pm
· Te'amo Boba - Water Tower Place · 11:00 am - 7:00 pm
· Te'amo Boba Bar · 11:00 am - 8:00 pm
· Uni Uni Boba · 11:00 am - 10:00 pm
· McDonald's HQ Restaurant · 8:00 am - 5:00 pm
· McDonald's Walk-Up Window · 5:00 am - 12:00 am
· City Winery · 10:00 am - 10:00 pm
· Manny's Deli · 8:00 am - 7:30 pm
· Michael's Original Pizzeria & Tavern · 11:00 am - 11:00 pm
· Oasis Cafe · 10:30 am - 4:00 pm
· Redhot Ranch · 10:30 am - 12:00 am
· Zaza's Pizzeria · 12:00 pm - 9:00 pm
Thu · Apr 9
Departure Day
🚂 DEPARTURE
Check out of River Hotel. Amtrak departs Union Station · 3:05 pm. Allow time to get to Canal St — Union Station is a short walk/taxi from the Loop. Lou Mitchell's is literally steps away if you want a final breakfast.
Mostly Sunny
↑ 59°F
↓ 39°F
🌅 6:21 am · 🌇 7:24 pm
Good morning for a final walk before Union Station.
Open today
· Firecakes Donuts - Lincoln Park · 6:30 am - 7:00 pm
· Firecakes Donuts - River North · 6:30 am - 11:00 pm
· Lou Mitchell's · 6:00 am - 2:00 pm
· Te'amo Boba - Chinatown · 11:00 am - 10:00 pm
· Te'amo Boba - River North · 12:00 pm - 9:30 pm
· Te'amo Boba - Water Tower Place · 11:00 am - 7:00 pm
· Te'amo Boba Bar · 11:00 am - 8:00 pm
· Uni Uni Boba · 11:00 am - 10:00 pm
· McDonald's HQ Restaurant · 8:00 am - 5:00 pm
· McDonald's Walk-Up Window · 5:00 am - 12:00 am
· City Winery · 10:00 am - 10:00 pm
· Manny's Deli · 8:00 am - 7:30 pm
· Michael's Original Pizzeria & Tavern · 11:00 am - 11:00 pm
· Oasis Cafe · 10:30 am - 4:00 pm
· Redhot Ranch · 10:30 am - 12:00 am
· Zaza's Pizzeria · 12:00 pm - 9:00 pm
Things to See
Parks, architecture, history, weird stuff — the full Chicago experience.
Architecture & History
Essanay Studios
1345 W Argyle St · Uptown
Where Charlie Chaplin and Gloria Swanson got their start. The terra cotta Indian head is still on the building.
📍 Maps
Nike Missile Site C-44
11709 S Ave F · South Lakefront
Cold War relic. One of the missile battery sites that ringed Chicago in the 1950s-60s. Surprisingly intact.
📍 Maps
Nuclear Energy Sculpture
S Ellis Ave & E 57th St · Hyde Park / UChicago
Henry Moore sculpture marking where the first controlled nuclear reaction occurred in 1942. Wild to stand there.
📍 Maps
Obama House
5046 S Greenwood Ave · Kenwood
Barack Obama's Chicago home. Street is accessible; security perimeter around the house itself.
📍 Maps
The Rookery
209 S LaSalle St · The Loop
1888 landmark. Frank Lloyd Wright redesigned the interior light court. Free to walk in during business hours.
📍 Maps
Union Stock Yard Gate
850 W Exchange Ave · Back of the Yards
All that remains of the massive stockyards that shaped Chicago. National Historic Landmark.
📍 Maps
Museum
Driehaus Museum
50 E Erie St · Near North Side
The museum is located just steps from the Magnificent Mile. The museum's collection reflects and is inspired by the collecting interests, vision, and focus of its founder, the late Richard H. Driehaus.
📍 Maps
Griffin Museum of Science and Industry
5700 S Lake Shore Dr · Hyde Park
One of the largest science museums in the world, Griffin MSI has both an illustrious history and a focus on the future of science and science education.
📍 Maps
Music & Entertainment
Chicago Fire TV Firehouse
1360 S Blue Island Ave · Pilsen
Filming location for the NBC show. Working firehouse — respect the crew, but the exterior is publicly accessible.
📍 Maps
Kingston Mines
2548 N Halsted St · Lincoln Park
Chicago's oldest continuously operating blues club. Two stages running simultaneously. Only open Thu-Sun — plan accordingly.
📍 Maps
Navy Pier
600 E Grand Ave · Streeterville
Tourist, yes — but the lakefront views are genuinely great. Good spot early morning before the crowds arrive.
📍 Maps
Parks & Nature
Bloomingdale Trail "The 606"
1600 W Bloomingdale Ave · Logan Square
The 606 is a transformative project that turned an old railroad embankment into a 2.7-mile-long recreational trail and park system.
📍 Maps
Burnham Park Promontory Point
5491 S Lake Shore Dr · Hyde Park
A man-made peninsula jutting into Lake Michigan in the Hyde Park neighborhood, built as part of the lakefront park system in the 1930s. It's beloved by locals for its stunning 270-degree views of the Chicago skyline — arguably the best skyline view in the city that isn't from a skyscraper. The limestone fieldhouse at the tip is a Chicago landmark, and the surrounding park is a popular spot for picnics, swimming, and watching sunsets over the water.
📍 Maps
Chicago Botanic Garden
1000 Lake Cook Rd · Glencoe (north suburb)
Stunning. Worth the Metra ride — Union Pacific North line to Braeside or Glencoe stop.
📍 Maps
Garfield Park Conservatory
300 N Central Park Ave · Garfield Park
One of the largest conservatories in the world. Lush tropical greenhouses — perfect for early spring.
📍 Maps
Grant Park
337 E Randolph St · The Loop
Chicago's front yard. The Bean, Buckingham Fountain, Millennium Park all connected here.
📍 Maps
Lincoln Park Zoo
2204 N Cannon Dr · Lincoln Park
Lincoln Park Zoo is home to a wide variety of animals and is one of a small number of zoos to offer free admission.
📍 Maps
Weird & Offbeat
"Shit Fountain"
1001 N Wolcott Ave · Wicker Park
A giant bronze coil of feces is both a tribute to doggie defecation and a reminder to pick it up.
📍 Maps
Alley of Death and Mutilation
S Wabash Ave between 26th & 27th St · South Loop
Grim nickname for an alley with a notorious accident history in the early 20th century. Part of Chicago's dark tourism circuit.
📍 Maps
Rosehill Cemetery
5800 N Ravenswood Ave · Ravenswood
Chicago's largest cemetery. Incredible Victorian architecture, mausoleums, and notable Chicagoans buried here. Actually beautiful in spring.
📍 Maps
Food & Coffee
Hours verified March 2026. Several places have unusual closures — check before you go. See Overview tab for a day-by-day breakdown.
Breakfast & Pastries
Firecakes Donuts - Lincoln Park
2453 N Clark St · Lincoln Park
Second Chicago location. Closer to Kingston Mines — good combo if you're in the neighborhood for a blues night.
Hours
Mon6:30 am - 5:00 pm
Tue6:30 am - 5:00 pm
Wed6:30 am - 5:00 pm
Thu6:30 am - 7:00 pm
Fri6:30 am - 7:00 pm
Sat6:30 am - 7:00 pm
Sun6:30 am - 7:00 pm
Firecakes Donuts - River North
68 W Hubbard St · River North
Small-batch artisan donuts made from scratch. Walk-up window available. Go early — popular flavors sell out. La Colombe coffee.
Hours
Mon6:30 am - 9:00 pm
Tue6:30 am - 9:00 pm
Wed6:30 am - 9:00 pm
Thu6:30 am - 11:00 pm
Fri6:30 am - 11:00 pm
Sat6:30 am - 11:00 pm
Sun6:30 am - 9:00 pm
Lou Mitchell's
565 W Jackson Blvd · West Loop
Chicago institution since 1923. Milk Duds while you wait, Greek omelettes, thick toast. Near Union Station and the start of Route 66. Breakfast served all day.
Hours
MonClosed
TueClosed
Wed6:00 am - 2:00 pm
Thu6:00 am - 2:00 pm
Fri6:00 am - 2:00 pm
Sat7:00 am - 2:00 pm
Sun7:00 am - 2:00 pm
Coffee & Boba
Te'amo Boba - Chinatown
2169 A S China Pl · Chinatown
Organic bubble tea, mochi donuts, macarons. Award-winning nonalcoholic drink menu (Chicago Tribune 2023).
Hours
Mon11:00 am - 10:00 pm
Tue11:00 am - 10:00 pm
Wed11:00 am - 10:00 pm
Thu11:00 am - 10:00 pm
Fri11:00 am - 10:30 pm
Sat11:00 am - 10:30 pm
Sun11:00 am - 10:00 pm
Te'amo Boba - River North
520 N Michigan Ave Suite 421 · River North
Organic bubble tea, mochi donuts, macarons. Award-winning nonalcoholic drink menu (Chicago Tribune 2023).
Hours
Mon12:00 pm - 9:30 pm
Tue12:00 pm - 9:30 pm
Wed12:00 pm - 9:30 pm
Thu12:00 pm - 9:30 pm
Fri12:00 pm - 9:30 pm
Sat12:00 pm - 10:00 pm
Sun12:00 pm - 9:30 pm
Te'amo Boba - Water Tower Place
835 N Michigan Ave Floor 2 · Streeterville
Organic bubble tea, mochi donuts, macarons. Award-winning nonalcoholic drink menu (Chicago Tribune 2023).
Hours
Mon11:00 am - 7:00 pm
Tue11:00 am - 7:00 pm
Wed11:00 am - 7:00 pm
Thu11:00 am - 7:00 pm
Fri11:00 am - 8:00 pm
Sat11:00 am - 8:00 pm
Sun12:00 pm - 6:00 pm
Te'amo Boba Bar
36 S Michigan Ave · Millennium Park
Organic bubble tea, mochi donuts, macarons. Award-winning nonalcoholic drink menu (Chicago Tribune 2023). Additional locations at 520 N Michigan and 835 N Michigan.
Hours
Mon11:00 am - 8:00 pm
Tue11:00 am - 8:00 pm
Wed11:00 am - 8:00 pm
Thu11:00 am - 8:00 pm
Fri11:00 am - 8:30 pm
Sat11:00 am - 9:00 pm
Sun11:00 am - 8:00 pm
Uni Uni Boba
2171 S China Pl · Chinatown
Uni Uni aims to bring our customers a unique bubble tea experience by offering a variety of healthy drinks made with high-quality ingredients. Driven by the craftsman spirit, Uni Uni focuses on every single detail of the tea-brewing process to present a flawless taste and appearance.
Hours
Mon11:00 am - 10:00 pm
Tue11:00 am - 10:00 pm
Wed11:00 am - 10:00 pm
Thu11:00 am - 10:00 pm
Fri11:00 am - 11:00 pm
Sat11:00 am - 11:00 pm
Sun11:00 am - 11:30 pm
Fast Food
McDonald's HQ Restaurant
110 N Carpenter St · Fulton Market
Flagship McDonald's inside the global HQ. Rotating Global Favorites menu with international items. Kiosk ordering, no drive-thru. Enter off Randolph St. Former site of Harpo Studios.
Hours
Mon8:00 am - 5:00 pm
Tue8:00 am - 5:00 pm
Wed8:00 am - 5:00 pm
Thu8:00 am - 5:00 pm
Fri8:00 am - 5:00 pm
SatClosed
SunClosed
McDonald's Walk-Up Window
180 W Adams St · The Loop
The Rock N Roll McDonald's — a Chicago peculiarity. Walk-up window on the street. Open 24 hours every day.
Hours
Mon5:00 am - 12:00 am
Tue5:00 am - 12:00 am
Wed5:00 am - 12:00 am
Thu5:00 am - 12:00 am
Fri5:00 am - 12:00 am
Sat5:00 am - 12:00 am
Sun5:00 am - 12:00 am
Lunch & Dinner
City Winery
11 Riverwalk · The Loop
We invite you to Indulge Your Senses in the heart of Chicago. Our Riverwalk wine garden offers locally-produced wine, cocktails and beer with spectacular city views along with delicious food to pair.
Hours
Mon10:00 am - 10:00 pm
Tue10:00 am - 10:00 pm
Wed10:00 am - 10:00 pm
Thu10:00 am - 10:00 pm
Fri10:00 am - 10:00 pm
Sat10:00 am - 10:00 pm
Sun10:00 am - 10:00 pm
Manny's Deli
1141 S Jefferson St · Near West Side
Manny’s Cafeteria & Delicatessen is a cornerstone of Chicago’s food scene. Serving up classic Jewish deli sandwiches, fresh bagels, and homestyle comfort food since 1942, we’ve been the go-to lunch spot for generations of locals, politicians, and visitors alike.
Hours
MonClosed
Tue8:00 am - 7:30 pm
Wed8:00 am - 7:30 pm
Thu8:00 am - 7:30 pm
Fri8:00 am - 7:30 pm
Sat8:00 am - 7:30 pm
Sun8:00 am - 3:30 pm
Michael's Original Pizzeria & Tavern
4091 N Broadway St · Uptown / Buena Park
Classic Chicago tavern-style pizza. 30+ HDTVs, sports bar, dog-friendly patio. Deep dish and thin crust. Open every day.
Hours
Mon11:00 am - 11:00 pm
Tue11:00 am - 11:00 pm
Wed11:00 am - 11:00 pm
Thu11:00 am - 11:00 pm
Fri11:00 am - 11:00 pm
Sat11:00 am - 11:00 pm
Sun11:00 am - 10:00 pm
Oasis Cafe
21 N Wabash Ave · The Loop
Mediterranean — gyros, falafel, shawarma, spanakopita. Featured on Food Network's Best Thing I Ever Ate. Compact lunch spot, democratic prices. Lunch-only hours.
Hours
Mon10:30 am - 4:00 pm
Tue10:30 am - 4:00 pm
Wed10:30 am - 4:00 pm
Thu10:30 am - 4:00 pm
Fri10:30 am - 4:00 pm
Sat11:00 am - 3:00 pm
SunClosed
Redhot Ranch
2449 W Armitage Ave · Humboldt Park
Red Hot Ranch Is a fast food Hot dog stand featuring the depression or minimalist style hot dog, fresh cut fries and homemade french fried shrimp
Hours
Mon10:30 am - 12:00 am
Tue10:30 am - 12:00 am
Wed10:30 am - 12:00 am
Thu10:30 am - 12:00 am
Fri10:30 am - 12:00 am
Sat10:30 am - 12:00 am
Sun10:30 am - 12:00 am
Zaza's Pizzeria
3037 N Clark St · Lakeview East
NY-style artisan pizza. BYOB — bring a bottle of wine. Rated 8.2 by Barstool Sports. Second location at 1521 N Fremont, Lincoln Park.
Hours
MonClosed
Tue4:00 pm - 9:00 pm
Wed12:00 pm - 9:00 pm
Thu12:00 pm - 9:00 pm
Fri12:00 pm - 9:00 pm
Sat12:00 pm - 9:00 pm
Sun12:00 pm - 9:00 pm
Chicago Neighborhoods
Wander zones — great for food, shopping, and general vibes.
Chinatown
One of the largest Chinatowns in the Midwest. Centered on Wentworth Ave & Cermak Rd. Excellent dim sum, bubble tea, bakeries, and Chinatown Square Mall. Easy Red Line access.
Little Italy
UIC-adjacent stretch of Taylor St. Classic Italian-American restaurants, pastry shops, some old school Chicago flavor. Al Capone used to run things around here.
Pilsen District (Lower West Side)
Pilsen is Chicago's historic Mexican-American cultural hub on the Lower West Side, packed with some of the best authentic Mexican food in the city alongside taquerias, bakeries, and restaurants that have been feeding the neighborhood for generations. It's also become one of Chicago's premier arts neighborhoods, with the National Museum of Mexican Art, dozens of independent galleries, and an explosion of colorful murals covering nearly every available wall.
Ukrainian Village
Residential neighborhood west of Wicker Park. Beautiful historic churches (Saints Volodymyr & Olha is stunning), Eastern European bakeries, and a genuine community feel. Low-key and walkable.
Where You're Staying
Two properties across the trip — starting in Cicero, finishing in the Loop. Amtrak bookends both ends.
🚂 Amtrak · Union Station
Chicago Union Station
225 S Canal St · West Loop
Your gateway in and out of Chicago. The Great Hall is worth a few minutes of gawking — one of the great train station interiors in the US.
Your Trains
Arrival — Sun Mar 294:45 pm
Departure — Thu Apr 93:05 pm
Lou Mitchell's is a 5-minute walk on Jackson Blvd — perfect for a final breakfast before your 3:05pm departure.
🏨 Property 1 · Mar 29 – Apr 3
The Shamrock
1212 S. Cicero Ave. · Cicero, IL 60804
Located in Cicero, just west of Chicago. The Pink Line (54th/Cermak station) or bus routes connect you into the Loop in ~25–35 min. Cicero Ave is a straight shot north into the city by car or rideshare.
🏨 Property 2 · Apr 3 – Apr 9
River Hotel
75A E. Wacker Dr. · Chicago, IL 60601
Prime Loop location right on the Chicago River, steps from Millennium Park, the Art Institute, and virtually every L line. Michigan Ave is a 5-minute walk. Lou Mitchell's is ~15 min on foot down Jackson — ideal for your departure morning.
🚇 Getting Around
CTA 'L' Train
Chicago Transit Authority
Eight color-coded lines. Red Line and Blue Line run 24/7. Buy a Ventra card at any station for easy tap-in access.
🗺 CTA Map
Ventra App / Card
Mobile transit payment
Single rides $2.50. 1-day pass $5 · 3-day $15 · 7-day $20. Load on your phone or buy a physical card at any station.
📱 Ventra Site
Metra Commuter Rail
For suburban destinations
Need this for Chicago Botanic Garden — Union Pacific North line to Braeside or Glencoe stop.
🚆 Metra Site
Map & Directions
Click any pin to add it to the route builder. Color coded by type.
Show:
Map of Chicago's Community Areas
Chicago Scrapbook
Photos and videos from your trip, tagged by location, food, day, and more. The media is sorted from newest to oldest.
Drop photos & videos here, or click to browse
JPG, PNG, GIF, WEBP, MP4, MOV — multiple files OK
No photos yet — upload some above to get started!
Your scrapbook will be saved in your browser.