- Must visit
Art Institute Of Chicago
One of the world’s leading art museums, famous for Impressionist masterpieces, American art, and major special exhibitions.
Flights from Wisconsin Dells, WI to Chicago, IL depart on average 17 times per day, taking around 1h 12m. Cheap flight tickets for this journey start at $214 (€173) but you can travel from only $25 (€20) by train.
There are 9 flights per day. The earliest flight runs at 00:02, the last at 23:55. The fastest flight covers the 163 miles (263 km) distance in 1h 3m. June is the cheapest month to fly.
Distance 163 miles (263 km) |
Average flight duration 1h 12m |
Cheapest ticket price $214 (€173) |
Flights per day 17 |
Direct flights 9 |
Fastest flight 1h 3m |
First flight 12:02 AM |
Last flight 11:55 PM |
Cheapest Month Jun |
Cheapest Day Sat |
High Season Jul - Sep |
Low Season Apr - Jun |
Busiest Day Fri |
Least Busy Day Mon |
Best time to book 35 days |
Cheapest price
$377
Average price
$615
Fastest journey
1 h 10 m
Average duration
1 h 11 m
Flights per day
21
Distance
263 km
The best way to find a cheap flight ticket from Wisconsin Dells, WI to Chicago, IL is to book your journey as far in advance as possible and to avoid traveling at rush hour.
The average ticket from Wisconsin Dells, WI to Chicago, IL will cost around $615 if you buy it on the day, but the cheapest tickets can be found for only $377.
Of the 21 flights that leave Wisconsin Dells, WI for Chicago, IL onThu, Jun 04, 11 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Thu, Jun 04 the direct flights cover the 263 km distance in an average of 1 h 11 m but if you time it right, some flights will get you there in just 1 h 10 m .
On Thu, Jun 04 the longest flights will take 1 h 12 m and usually involve a change or two along the way, but you might be able to save a few pennies if you’re on a budget.
UA5598
UA2137
UA2151
UA5358
UA529
UA2137
UA2151
UA5598
UA529
AA3716Omio recommends booking the train as it is the most popular option from Wisconsin Dells, WI to Chicago, IL among Omio's users. If you are prioritising price take the bus with prices starting from $34. For those with little time consider booking a flight which can get you there in 1h 12m. The ticket price range depends on the travel mode: a bus costs an average of $34, and a flight costs an average of $214.
Distance: 163 miles (263 km)
| Flight | Most popular Train | Bus | Driving |
|---|---|---|---|
$347 Average price | $61 Average price | $54 Average price Cheapest | $45 Average price (fuel + tolls) |
4h 12m Average total duration Fastest 1h 12m Onboard + 3h 0m Additional time* | 4h 15m Average total duration 3h 45m Onboard + 30m Additional time* | 5h 3m Average total duration 4h 33m Onboard + 30m Additional time* | 2h 59m Average total duration (door-to-door) |
Direct Options | Direct Options | Direct Options | Direct Options |
This is compared to other travel options from Wisconsin Dells, WI to Chicago, IL:
A bus is $8 (€6) less than a train for this route with tickets for a train from Wisconsin Dells, WI to Chicago, IL costing on average $61 (€49).
A bus is $293 (€237) less than a flight for this route with tickets for a flight from Wisconsin Dells, WI to Chicago, IL costing on average $347 (€281).
Other travel options to Chicago, IL take longer:
Train takes on average 3h 45m.
Bus takes on average 4h 33m.
The table below shows live departures for Wisconsin Dells, WI to Chicago, IL flights for today, Wednesday, June 3. You can also manually refresh the results below to see updated flight journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
![]() | 5:13 PM Wisconsin Dells, WI | 1h10 | 6:23 PM Chicago, IL | 0 transfersDirect | |
![]() | 6:32 PM Wisconsin Dells, WI | 1h21 | 7:53 PM Chicago, IL | 0 transfersDirect | |
| Thursday, June 4 | |||||
UA5545 · UA2430 | 5:00 AM Dane County Regional Airport | 6h44 | 11:44 AM O'Hare International Airport | 1 transfer | |
UA5545 · UA1928 | 5:00 AM Dane County Regional Airport | 6h23 | 11:23 AM O'Hare International Airport | 1 transfer | |
AA4322 | 5:00 AM Dane County Regional Airport | 1h15 | 6:15 AM O'Hare International Airport | 0 transfersDirect | |
UA5545 · UA2329 | 5:00 AM Dane County Regional Airport | 8h15 | 1:15 PM O'Hare International Airport | 1 transfer | |
UA3482 · UA1875 | 6:24 AM Dane County Regional Airport | 6h44 | 1:08 PM O'Hare International Airport | 1 transfer | |
UA3482 · UA2053 | 6:24 AM Dane County Regional Airport | 8h19 | 2:43 PM O'Hare International Airport | 1 transfer | |
UA2137 | 6:30 AM Dane County Regional Airport | 1h10 | 7:40 AM O'Hare International Airport | 0 transfersDirect | |
AA4688 | 6:34 AM Dane County Regional Airport | 1h26 | 8:00 AM O'Hare International Airport | 0 transfersDirect | |
UA2151 | 8:05 AM Dane County Regional Airport | 1h10 | 9:15 AM O'Hare International Airport | 0 transfersDirect | |
AA4018 | 8:22 AM Dane County Regional Airport | 1h23 | 9:45 AM O'Hare International Airport | 0 transfersDirect | |
UA2360 · UA2865 | 8:50 AM Dane County Regional Airport | 6h05 | 2:55 PM O'Hare International Airport | 1 transfer | |
UA2360 · UA617 | 8:50 AM Dane County Regional Airport | 8h15 | 5:05 PM O'Hare International Airport | 1 transfer | |
UA5358 | 10:40 AM Dane County Regional Airport | 1h17 | 11:57 AM O'Hare International Airport | 0 transfersDirect | |
UA3675 · UA661 | 10:52 AM Dane County Regional Airport | 7h42 | 6:34 PM O'Hare International Airport | 1 transfer | |
AA3437 | 12:08 PM Dane County Regional Airport | 1h13 | 1:21 PM O'Hare International Airport | 0 transfersDirect | |
This is the last flight of the day. | |||||
Find all the dates and times for this journey
Compare train, bus, and flight prices over the next three weeks. See the best deals at a glance, find the lowest fares, and choose the option that fits your budget.
Discover the best of Chicago — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Chicago trip today.
One of the world’s leading art museums, famous for Impressionist masterpieces, American art, and major special exhibitions.
Major natural history museum known for Sue the T. rex, ancient cultures, and large family-friendly science exhibits.
Large hands-on science museum in Hyde Park with a U-505 submarine, aviation exhibits, and immersive interactive displays.
Chicago’s signature public space, home to Cloud Gate and major events, with strong appeal for first-time visitors and photographers.
Scenic pedestrian route along the Chicago River, popular for architecture views, strolling, and social-media-friendly city scenes.
Famous stretch of North Michigan Avenue known for landmark architecture, flagship stores, and busy big-city energy.
Chicago’s iconic thick-crust pizza baked in a deep pan with layers of cheese, toppings, and chunky tomato sauce.
An all-beef hot dog on a poppy seed bun topped with mustard, onions, relish, tomato, pickle spear, sport peppers, and celery salt.
A classic Chicago sandwich of thin-sliced seasoned beef served on a roll, often dipped in jus and topped with giardiniera or sweet peppers.
A well-known Magnificent Mile restaurant serving Mediterranean-influenced small plates, charcuterie, and strong wine selections.
Chicago’s internationally acclaimed fine-dining restaurant known for inventive tasting menus and a polished, theatrical experience.
A legendary Chicago pizzeria best known for buttery-crust deep-dish pizza in a casual, family-friendly setting.
Moderate by U.S. big-city standards. Hotels can be pricey downtown, but food and transit offer good value.
Tip 18-20% at sit-down restaurants; 20%+ for great service. USD 1-2 per drink at bars, round up or 10-15% for taxis, and USD 1-2 per bag for hotel staff.
Find answers to the most common questions about traveling from Wisconsin Dells, WI to Chicago, IL by flight. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest flight, the cheapest option, or tips for making the most of your visit at Chicago, IL, this guide helps you travel smarter and with confidence.

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