Cheap flights from HDN to MDW (Yampa Valley to Midway Intl.)

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Cheap Flights from HDN to MDW starting at $215 One Way, Round Trip

Prices starting at for return flights and $215 for one-way flights to Midway Intl. were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
$146 nightly
The price is $171 total per night from Aug 24 to Aug 25
$171 total
Aug 24 - Aug 25
Total includes taxes and fees
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
8.8/10 Excellent! (1,335 reviews)
"Thanks beautiful place"

Reviewed on Aug 3, 2025

Crowne Plaza Chicago West Loop by IHG
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
$157 nightly
The price is $184 total per night from Sep 1 to Sep 2
$184 total
Sep 1 - Sep 2
Total includes taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (8,944 reviews)
"good"

Reviewed on Aug 2, 2025

Congress Plaza Hotel
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
506 West Harrison Street, Chicago, IL
$154 nightly
The price is $181 total per night from Sep 2 to Sep 3
$181 total
Sep 2 - Sep 3
Total includes taxes and fees
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.2/10 Very Good! (1,009 reviews)
"Coffee in the lobby would be nice"

Reviewed on Aug 1, 2025

Holiday Inn & Suites Chicago - Downtown by IHG
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotels In Chicago

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
$157 nightly
The price is $184 total per night from Sep 1 to Sep 2
$184 total
Sep 1 - Sep 2
Total includes taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (8,944 reviews)
"good"

Reviewed on Aug 2, 2025

Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
$198 nightly
The price is $229 total per night from Aug 21 to Aug 22
$229 total
Aug 21 - Aug 22
Total includes taxes and fees
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and ...
8.2/10 Very Good! (1,817 reviews)
"Third stay at the Palmer House. We'll be back."

Reviewed on Jul 31, 2025

Palmer House a Hilton Hotel
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
$146 nightly
The price is $171 total per night from Aug 24 to Aug 25
$171 total
Aug 24 - Aug 25
Total includes taxes and fees
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
8.8/10 Excellent! (1,335 reviews)
"Thanks beautiful place"

Reviewed on Aug 3, 2025

Crowne Plaza Chicago West Loop by IHG
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Chicago Hotels With Airport Transportation

Motel 6 Elk Grove Village, IL - O'Hare

Motel 6 Elk Grove Village, IL - O'Hare

2 out of 5
2881 Touhy Ave, Elk Grove Village, IL
$60 nightly
The price is $68 total per night from Aug 20 to Aug 21
$68 total
Aug 20 - Aug 21
Total includes taxes and fees
Stay at this motel in Elk Grove Village. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (1,578 reviews)
"Excellent stay."

Reviewed on Aug 2, 2025

Motel 6 Elk Grove Village, IL - O'Hare
Country Inn & Suites by Radisson, Chicago O'Hare South, IL

Country Inn & Suites by Radisson, Chicago O'Hare South, IL

3 out of 5
777 E Grand Avenue, Bensenville, IL
$107 nightly
The price is $119 total per night from Aug 10 to Aug 11
$119 total
Aug 10 - Aug 11
Total includes taxes and fees
Stay at this 3-star golf hotel in Bensenville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our ...
7/10 Good! (1,000 reviews)
"It was noisy. Otherwise, everything else was good."

Reviewed on Aug 1, 2025

Country Inn & Suites by Radisson, Chicago O'Hare South, IL
Comfort Suites Chicago O'Hare Airport

Comfort Suites Chicago O'Hare Airport

3 out of 5
4200 North River Road, Schiller Park, IL
$93 nightly
The price is $106 total per night from Aug 17 to Aug 18
$106 total
Aug 17 - Aug 18
Total includes taxes and fees
Stay at this 3-star business-friendly hotel in Schiller Park. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and ...
8/10 Very Good! (2,572 reviews)
"It was an amazing night."

Reviewed on Aug 4, 2025

Comfort Suites Chicago O'Hare Airport
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Low Priced Chicago Hotels

Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
$147 nightly
The price is $172 total per night from Aug 24 to Aug 25
$172 total
Aug 24 - Aug 25
Total includes taxes and fees
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. ...
7.8/10 Good! (2,144 reviews)
"Really fun"

Reviewed on Aug 3, 2025

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St, Chicago, IL
$107 nightly
The price is $126 total per night from Aug 25 to Aug 26
$126 total
Aug 25 - Aug 26
Total includes taxes and fees
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
7.2/10 Good! (2,270 reviews)
Great for the center
"Excellent and in the centre"

Reviewed on Aug 1, 2025

Travelodge by Wyndham Downtown Chicago
Motel 6 Elk Grove Village, IL - O'Hare

Motel 6 Elk Grove Village, IL - O'Hare

2 out of 5
2881 Touhy Ave, Elk Grove Village, IL
$60 nightly
The price is $68 total per night from Aug 20 to Aug 21
$68 total
Aug 20 - Aug 21
Total includes taxes and fees
Stay at this motel in Elk Grove Village. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (1,578 reviews)
"Excellent stay."

Reviewed on Aug 2, 2025

Motel 6 Elk Grove Village, IL - O'Hare
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Family Friendly Hotels in Chicago

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

4 out of 5
511 North Columbus Drive, Chicago, IL
$199 nightly
The price is $233 total per night from Aug 24 to Aug 25
$233 total
Aug 24 - Aug 25
Total includes taxes and fees
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the helpful ...
8.2/10 Very Good! (2,721 reviews)
"Excellent staff. Extremely friendly and helpful. The location was perfext for all the things we did while in Chicago."

Reviewed on Aug 3, 2025

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
$198 nightly
The price is $229 total per night from Aug 21 to Aug 22
$229 total
Aug 21 - Aug 22
Total includes taxes and fees
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and ...
8.2/10 Very Good! (1,817 reviews)
"Third stay at the Palmer House. We'll be back."

Reviewed on Jul 31, 2025

Palmer House a Hilton Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
$174 nightly
The price is $204 total per night from Sep 1 to Sep 2
$204 total
Sep 1 - Sep 2
Total includes taxes and fees
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
8.4/10 Very Good! (4,597 reviews)
"We had a nice stay, it was pretty quiet, our beds were comfortable, however we were missing a blanket on one. The pool was crowded because it was small and the kids said the water was cold. There was plenty of food at breakfast and a lot to choose from. It was a decent stay for the price I paid, ..."

Reviewed on Aug 1, 2025

Embassy Suites by Hilton Chicago Downtown River North
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

HDN to MDW Route Info

Origin Airport
Destination Airport
Number Of Airlines Serving
Distance
Shortest Flight Departure Time
Shortest Flight Departure Date

Frequently asked questions

Are there non-stop flights from Yampa Valley Airport (HDN) to MDW?
You're going to need to swap planes if you want to get from HDN to MDW. Numerous carriers operate on this route with just one stopover, including Southwest Airlines, Delta Air Lines and United Airlines.
What is the shortest flight from HDN to Chicago Airport?
The quickest flight from Yampa Valley Regional Airport to Chicago Airport is 4 hours and 6 minutes. Slip a few things into your carry-on to keep you amused, like the latest edition of your favorite magazine or a portable board game.
How many hours flight from Yampa Valley Airport (HDN) to Midway Airport?
The trip from Yampa Valley Regional Airport to Midway Airport will take around 4 hours and 13 minutes. A couple of good movies, some podcasts and a bit of shut-eye will help make time fly.
What airlines have the most flights from Yampa Valley Airport (HDN) to Chicago Airport?
You'll have to make one or more stopovers if you're flying from HDN to MDW. Unfortunately, there aren't any airlines that advertise direct flights on this route.

Map To Nearby Hotels

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.