Cheap Skiplagging Flight Deals to Chicago, IL (MDW)
What is Skiplagging? Skiplagging is a type of flight deal, also known as a hidden-city ticket, where you plan to get off at the layover city rather than the final, ticketed destination. Typically, airlines charge more for direct flights and less for flights with stops. When you see a flight marked as a "Skiplagging", that means this itinerary will continue on to another destination, but you will get off at the layover stop. The average savings for a hidden-city flight is $180.
There are no deals for this route right now.
Cheap flight deals to Chicago, IL (MDW)
With Skiplagged, you can find cheap flights going to Chicago, IL (MDW) from anywhere. We publish flight deals to MDW that can't be found anywhere else.
6:00 AM
5:45 PM
1 Stop
12h 45 min
Frontier Airlines
$139
9:40 AM
12:47 PM
1 Stop
4h 7 min
Delta Air Lines
$164
11:47 AM
4:47 PM
1 Stop
6h
Delta Air Lines
$164
12:57 PM
6:00 PM
1 Stop
6h 3 min
Delta Air Lines
$164
5:30 PM
10:33 PM
1 Stop
6h 3 min
Delta Air Lines
$164
7:10 AM
12:47 PM
1 Stop
6h 37 min
Delta Air Lines
$164
4:59 PM
11:43 PM
1 Stop
7h 44 min
Frontier Airlines
$173
9:40 AM
12:47 PM
1 Stop
4h 7 min
Delta Air Lines
$183
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Frequently Asked Questions
The major airports near Chicago, Illinois are Chicago O'Hare International Airport (ORD), Chicago Midway International Airport (MDW), Gary/Chicago International Airport (GYY), and Rockford International Airport (RFD).
The following airlines fly to Chicago, Illinois: American Airlines, United Airlines, Delta Air Lines, Southwest Airlines, JetBlue Airways, Frontier Airlines, Alaska Airlines, Allegiant Air, Air Canada, British Airways, KLM, Lufthansa, Air France, Aer Lingus, Virgin Atlantic, Qatar Airways, Emirates, and Turkish Airlines.
1. Millennium Park
2. The Art Institute of Chicago
3. Navy Pier
4. Willis Tower
5. Lincoln Park Zoo
6. Shedd Aquarium
7. The Magnificent Mile
8. Chicago Riverwalk
9. Garfield Park Conservatory
10. Museum of Science and Industry
The best way to get to Chicago from the airport is by taxi, rideshare, or public transportation. Depending on the airport, you may be able to take a train, bus, or shuttle to get to the city.
The best way to get to the airport from Chicago, Illinois is by taxi, rideshare, or public transportation. Depending on where you are located in the city, you can take the CTA Blue Line train to O'Hare International Airport or the Metra train to the airport. You can also take a taxi or rideshare service such as Uber or Lyft.
The weather in Chicago, Illinois varies throughout the year. In the summer months, temperatures typically range from the mid-60s to the mid-80s Fahrenheit (18-30 Celsius). In the winter months, temperatures typically range from the mid-20s to the mid-30s Fahrenheit (-4 to 1 Celsius).
1. Kayaking on the Chicago River
2. Biking along the Lakefront Trail
3. Picnicking in Millennium Park
4. Exploring the Chicago Botanic Garden
5. Taking a Segway Tour of the city
6. Visiting the Lincoln Park Zoo
7. Hiking in the Cook County Forest Preserves
8. Taking a boat tour of the city
9. Visiting the Museum Campus
10. Exploring the Garfield Park Conservatory
1. Visit the Art Institute of Chicago.
2. Take a tour of the Chicago Cultural Center.
3. Attend a performance at the Chicago Symphony Orchestra.
4. Explore the Museum of Science and Industry.
5. Take a stroll through Millennium Park.
6. Visit the Field Museum of Natural History.
7. Attend a show at the Chicago Theatre.
8. Explore the National Museum of Mexican Art.
9. Take a tour of the Chicago Architecture Foundation.
10. Attend a show at the Second City comedy club.
1. The Loop: Located in the heart of downtown Chicago, The Loop is a great neighborhood for visitors to stay in. It is home to many of the city’s most iconic attractions, including the Art Institute of Chicago, Millennium Park, and the Magnificent Mile.
2. Lincoln Park: This vibrant neighborhood is located on the north side of Chicago and is home to many of the city’s best restaurants, bars, and shops. It is also home to the Lincoln Park Zoo and the Chicago History Museum.
3. Wicker Park: This hip neighborhood is located on the northwest side of the city and is known for its trendy restaurants, bars, and boutiques. It is also home to the Wicker Park Farmers Market and the Wicker Park Music Festival.
4. Old Town: This historic neighborhood is located on the north side of the city and is home to many of the city’s oldest buildings. It is also home to the Second City comedy club and the Old Town Art Fair.
5. Hyde Park: This neighborhood is located on the south side of the city and is home to the University of Chicago. It is also home to the Museum of Science and Industry and the Robie House
The best transportation options in Chicago, Illinois include the Chicago Transit Authority (CTA) bus and train system, Divvy bike-sharing system, ride-sharing services such as Uber and Lyft, and taxis. The CTA is the most affordable option and provides access to most parts of the city. Divvy is a great option for short trips and is available throughout the city. Ride-sharing services and taxis are convenient and can be used for longer trips.
What other airports are close to Chicago, IL?
The following airports are nearby to and may be worth considering, as they could offer better pricing or more favorable schedules.
Cheap flights to Chicago, Illinois (CHI)
Cheap flights to Chicago, Illinois (ORD)
Cheap flights to Milwaukee, Wisconsin (MKE)
Cheap flights to South Bend, Indiana (SBN)
Things to do in Chicago, IL: Book local activities
Access the best deals to interesting local activities in Chicago, IL. Book your sightseeing experiences today to get the best selection of tickets.
City Tours in Chicago, IL
Chicago River 90-Minute Architecture Tour
1.5 hours. Be inspired by the captivating, visual art that is Chicago’s legendary architecture, and the exceptional architects who created this ever-changing, dynamic legacy for all to enjoy and admire. This comprehensive 90 minute tour will navigate through the heart of the city on all three branches of the Chicago River while your professionally-trained architectural guide tells the story of more than 130 years of innovation in design, style and technique and why it is important today. The Chicago River Architecture Tour is the most authentic and encompassing Chicago experience the city has to offer.
(11077 reviews)
Chicago Architecture River Cruise
1.5 hours. Experience the stunning beauty of Chicago on a captivating cruise along the historic Chicago River. This architectural tour takes you down the main branch of the river, up the north branch to the East Bank Club, and then south past the iconic Willis Tower (Sears Tower) to the historic Old Post Office Building.
Marvel at the magnificent city skyline as you pass by over 40 notable buildings, including:
John Hancock Center: An iconic skyscraper that defines the Chicago skyline.
Wrigley Building: Known for its distinctive white facade and clock tower.
As you sail, an expert architecture guide will provide fascinating insights into the distinctive designs and history of these architectural marvels. Whether you're a local or visiting for the first time, this tour offers a unique perspective on one of the world's most beautiful cities.
Sit back, relax, and let the architectural wonders of Chicago unfold before your eyes.
(17074 reviews)
Chicago Sightseeing River and Lake Cruise
1.5 hours. Our popular 90-minute daytime river and lake sightseeing tour delights family members of all ages with incredible views of Chicago's world-renowned buildings and stunning skyline. Lively, knowledgeable tour guides bring Chicago’s rich history to life with fun stories and interesting facts. Relax and unwind on a scenic tour of the city from the unique perspective of the Chicago River and Lake Michigan. Welcome aboard!
(742 reviews)
Lake Michigan Sunset Cruise in Chicago
1.5 hours. The Lake Michigan Sunset Cruise departs near the DuSable (Michigan Avenue) Bridge on Wendella's world class tour boats. The Cruise will navigate from the Chicago River, through the Chicago Lock and out onto Lake Michigan. Watch the sun slowly set behind the city from the tranquil waters of Lake Michigan on this serene and romantic cruise.
(1707 reviews)
Lake Michigan Skyline Cruise in Chicago
45 minutes. Embark on an unforgettable journey along Lake Michigan and marvel at Chicago's iconic lakefront sights and attractions.
Cruise along Lake Michigan and enjoy stunning views of Chicago's renowned skyscrapers from a unique vantage point. This tour offers an amazing opportunity to admire the city's breathtaking skyline and architectural wonders.
Sunday – Friday Cruises departing prior to 8:00pm feature recorded narration of the city’s skyline, cruises departing after 8:00pm enjoy some music and the sounds of Lake Michigan aboard our Groove Cruise.
November - April 9 tours are 30 minutes.
Highlights:
Spectacular views of Chicago's famous skyscrapers
Onboard bar serving refreshing drinks
Relaxing and enjoyable sightseeing cruise
Experience Chicago like never before on this serene and scenic Lake Michigan boat tour. Remember to bring your camera to capture those social media worthy photos!
(952 reviews)
Chicago River 90-Minute Architecture Boat Tour
1.5 hours. Marvel at the magnificent architecture on the Chicago River with expert tour guides! All ages welcome.
Each architecture river tour is narrated by a professional guide which leads passengers down the Chicago River to discover the city’s most renowned landmarks. In addition to historical insight on well known structures such as the Civic Opera House, Trump Tower & the Merchandise Mart, passengers will also get a chance to learn about current and upcoming developments. This Chicago River Cruise is the only cruise that navigates the three primary branches of the river including the main branch to Navy Pier, the north branch to Goose Island, and the south branch to Chinatown. It is also the cruise closest to Skydeck, has the least expensive parking, and is great for those coming from the suburbs due to its location off Interstate 290.
(1927 reviews)
Chicago Lake and River Architecture Tour
1.5 hours. An authentic Chicago tradition since 1935, this is the tour that started it all. This unique excursion tells the story of more than 200 years of fascinating social, cultural and political history, and explores more than a century of groundbreaking architecture. The journey begins with an up-close perspective of Chicago's internationally-known architecture as seen from the Chicago River. Then venture through the Chicago Lock on to the calm, cool waters of Lake Michigan for expansive views of Chicago's extraordinary 26-mile skyline. Take the selfie of a lifetime on this inspirational experience!
(2456 reviews)
Attractions & Museums in Chicago, IL
360 CHICAGO Observation Deck Admission
4 hours. The best views of Chicago can be yours at 360 Chicago Observation Deck! Perched 94 stories above the Windy City in the former John Hancock Building, 360 Chicago provides commanding views of Lake Michigan and Chicago’s towering skyscrapers. Located in the heart of downtown on Michigan Avenue, the observatory is steps away from other top Chicago attractions. It will be the high point (literally) of your Chicago trip!
Upgrade to the Sip and View ticket, which includes one drink at the newly renovated CloudBar. The Sip menu includes a rotating selection of beer, wine and cocktails. Once onsite, you can purchase tickets to TILT, a thrill ride that offers visitors unique, downward facing views from 1,030 feet. You may also choose to upgrade your Sip and View ticket from the Sip Menu to the Elevated Menu for an additional $8.
*TILT not included in purchase
(1318 reviews)
Flyover in Chicago
30 minutes. The Flyover experience takes 30 minutes from beginning to end. First, on-the-ground stories connect you with the spirit of the Windy City. Then, you’ll discover Chicago from a whole new perspective, as Flyover transports you over, around and through remarkable locations. You'll explore in motion with scenes captured by an award-winning creative team using custom-made drones and helicopter-mounted cameras, while scents, sounds and music deepen the immersion. It’ll take your breath away (we promise you’ll get it back).
(753 reviews)
Skydeck - Willis Tower Admission
1.5 hours. Gaze upon the city sights from the pinnacle of Chicago, the Skydeck. Located on the 103rd floor of Willis Tower, formerly Sears Tower -- the third-tallest building in the world -- the Skydeck offers spectacular sweeping views and is full of interactive exhibits. To complete your exciting Chicago experience, head to the Ledge, a glass balcony showcasing unbeatable views of Chicago’s top attractions like Wrigley Field and the Navy Pier.
We added a brand new Chicago Experience that you start with by the box office prior taking the elevator trip to the 103rd floor. It is a 45,000 sq ft. museum of today. The New Experience is part Chicago History, part Architecural tour, part Selfie Museum and part Children's Museum. This is fun and interactive for all ages. Ride our "L" Train, see our infinity pizza bed, take pictures ontop of Willis Tower and so much more! This is the best way to see Chicago in one setting.
With mobile tickets, simply scan your phone for direct entry into the SkyDeck
(1939 reviews)
Chicago CityPASS®
9 days. Experience 5 top attractions and save up to 50% with Chicago CityPASS® tickets. One simple purchase removes the stress of planning, so you can relax and enjoy your memories in the making. With 9 days to use your tickets, you’ll have plenty of time to explore the best sights.
Chicago CityPASS® bundles one-time admission to 5 attractions.
Includes:
• Chicago's Famous Aquarium
• Skydeck Chicago
Plus choose 3 more attractions.
• Shoreline Sightseeing Architecture River Tour
• Field Museum
• 360 CHICAGO Observation Deck
• Griffin Museum of Science and Industry
• Art Institute of Chicago
• Adler Planetarium
(542 reviews)
Architecture Tours in Chicago, IL
Chicago Architecture Center River Cruise aboard First Lady
1.5 hours. The Chicago Architecture Center River Cruise aboard Chicago's First Lady has long been the gold standard among all Chicago tour experiences, and is the only Chicago architecture boat tour led by highly trained expert docents. On this 90-minute cruise, you will enjoy an overview of historic and modern architectural styles including stories about the people who designed and built Chicago.
As a certified nonprofit, all ticket purchases directly support education efforts and community engagement projects. No visit to Chicago is complete without experiencing this award winning tour, so accept no substitutes.
(7302 reviews)
Chicago Hop-on Hop-off Sightseeing Tour by Open-top Bus
2 hours. Discover Chicago at your own pace with Big Bus. Travel aboard an open-top, double-decker bus and enjoy panoramic views of the city's most famous landmarks, including the Magnificent Mile, Millennium Park, Willis Tower, The Bean, Navy Pier and more.
Hop on and off at conveniently located stops to explore Chicago's top attractions, vibrant neighbourhoods, world-class dining and shopping. Use our free app to track bus arrivals in real time and plan your day with ease.
Enjoy multilingual digital commentary throughout your journey, packed with fascinating stories, local insights and recommendations.
48-hour and 72-hour tickets also include 4 Self-Guided Audio Walking Tours, covering topics such as Architecture, the Chicago Riverwalk and Public Art.
The 72-hour Explore option also includes the Chicago South Side & Presidential Center Shuttle, connecting Downtown Chicago with the Obama Presidential Center & Jackson Park and the Griffin Museum of Science & Industry.
(2411 reviews)
Chicago Seadog River & Lake Architectural Tour
1.25 hours. Soak in unobstructed views of Chicago’s world-famous architecture from the water with an exciting ride on our Seadog River and Lake Architectural Tour! Sail through the Chicago Harbor Locks to the River’s iconic skyscrapers. Enjoy amusing and informative narration for a fascinating tour through the city’s architectural history as you pass the Civic Opera House, the Merchandise Mart, and the Willis Tower. Buckle up for a thrilling finale on Lake Michigan to top off this family and dog-friendly experience and cruise along the skyline at top Seadog speed!
(307 reviews)
Chicago River 45-Minute Architecture Tour from Magnificent Mile
45 minutes. Experience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire. This family-friendly introduction to the Windy City's rich history and architectural heritage features highlights from Wendella's full-length architecture tours. Hop aboard our world class vessels as our local authentic tour guides showcase our amazing city.
(3654 reviews)