Cheap flights To Waterman (DPA)

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Waterman Flight Information

Traveling To
Waterman
Destination Airport IATA Code
DPA
Number of Airlines Serving
Airlines
Flight Price
Earliest Departing Flight
Latest Departing Flight

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Waterman economy flight packages

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

Nov 13 - Nov 15

2 night stay

Atlanta (ATL) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $818, price is now $528 per person
$528
per person
found 1 day ago
Level Chicago - River North
4.0-star property

Level Chicago - River North

Oct 31 - Nov 5

5 night stay

Atlanta (ATL) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,091, price is now $648 per person
$648
per person
found 1 day ago
Level Chicago Fulton Market
4.0-star property

Level Chicago Fulton Market

Oct 31 - Nov 5

5 night stay

Atlanta (ATL) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,018, price is now $619 per person
$619
per person
found 1 day ago
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Waterman premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Graduate by Hilton Evanston
4.0-star property

Graduate by Hilton Evanston

8.8/10 Excellent! (1,006 reviews)

Nov 21 - Nov 25

4 night stay

Miami (MIA) to Chicago (ORD)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,013, price is now $833 per person
$833
per person
found 16 hours ago
We really like it here - it's a bit quirky, but it's very comfortable and the staff are great.

Reviewed on May 28, 2025

Level Chicago - River North
4.0-star property

Level Chicago - River North

9/10 Wonderful! (698 reviews)

Nov 21 - Nov 25

4 night stay

Miami (MIA) to Chicago (ORD)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,107, price is now $913 per person
$913
per person
found 16 hours ago
The pool area is fantastic. Rooms very ample-sized and comfortable. I would stay here again!

Reviewed on Jul 8, 2024

Kimpton Gray Hotel by IHG
4.5-star property

Kimpton Gray Hotel by IHG

9.2/10 Wonderful! (1,007 reviews)

Nov 21 - Nov 25

4 night stay

Miami (MIA) to Chicago (ORD)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $989, price is now $877 per person
$877
per person
found 16 hours ago
Soaking tub suite, spacious and very cozy. No worries on taking the ice bucket to the ice machine. Pre bagged ice for convince. Very cool.

Reviewed on Aug 18, 2025

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Waterman first class flight packages

Price found within the past 48 hours. Click for updated prices.
Glenn Meadow Bed and Breakfast
4.0-star property

Glenn Meadow Bed and Breakfast

9.8/10 Exceptional! (79 reviews)

Nov 26 - Nov 29

3 night stay

Atlanta (ATL) to Chicago (ORD)

Delta • Roundtrip • FirstClass
Price was $1,348, price is now $1,298 per person
$1,298
per person
just found
I travel a lot and rarely leave reviews but wanted to take a minute to do so in this case. I highly recommend Glenn Meadow B&B. The price is reasonable, the home and location is very beautiful and peaceful, and the owner Tracey is a fantastic host who goes above and beyond. I accidentally left behind some expensive headphones and Tracey immediately shipped them back to me at no cost. On top of that she’s an excellent cook and breakfast was delicious. Can’t say enough good things about this place.

Reviewed on Sep 10, 2024

Victoria Resort and Bed & Breakfast
4.0-star property

Victoria Resort and Bed & Breakfast

9.4/10 Exceptional! (130 reviews)

Nov 26 - Nov 29

3 night stay

Atlanta (ATL) to Chicago (ORD)

Delta • Roundtrip • FirstClass
Price was $1,535, price is now $1,368 per person
$1,368
per person
just found
Elizabeth is a true gem of an employee! She’s a super chef, and a kind soul. She cared enough to prepare us kosher items. Her apple french toast and quiche were delicious. Our room was nice and the jacuzzi tub made for a great end to our days. Close to the beach and we used the resort bikes to go for a ride to the lighthouse. We were so impressed with Elizabeth’s hospitality that we talked our parents into coming and staying. We will be back. 10 out of 10 stars!! Treat yourself and enjoy the local wineries. Have Elizabeth prepare a charcuterie board for you and she’ll have it in the fridge in your room when you arrive, you won’t be sorry!

Reviewed on Oct 27, 2024

Old Harbor Inn
3.0-star property

Old Harbor Inn

9.4/10 Exceptional! (627 reviews)

Nov 26 - Nov 29

3 night stay

Atlanta (ATL) to Chicago (ORD)

Delta • Roundtrip • FirstClass
Price was $1,389, price is now $1,321 per person
$1,321
per person
just found
Clean, organized and beautiful views.

Reviewed on Jul 7, 2025

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Waterman

Finding cheap flights to Waterman is easy when you have Orbitz at your fingertips. Not only does Orbitz offer great deals on Waterman flights, but we also include some special extras to make booking a breeze. Just check out our:

Mobile Site and Apps

With Orbitz’s mobile site, m.orbitz.com, you can book your flights to Waterman through your smartphone or tablet’s Web browser. Plus, our free downloadable apps for Android and iPhone mean it’s just a simple click to access your flight updates and alerts. You can even book exclusive mobile-only deals on hotels to go with your flights to Waterman—even on the same day.

Pick and Choose or Book Full Vacation Packages

Don’t just be satisfied with great deals on Waterman flights—go for the full package! With Orbitz, you can also find fantastic savings on the perfect hotel, car rental, cruise, and even activities, so you don’t waste your trip waiting in line but have the time to enjoy your trip. Pick and choose the add-ons you need, or book an entire vacation package for greater overall discounts.

Rewards That Are Miles Better

Booking directly with an airline earns you air miles or points, and you can get those same rewards with booking on Orbitz too. When you book qualifying flights to Waterman with Orbitz, just add in your frequent flyer number during your online booking and your details will be sent to your program.

Great Deals Every Day

Add in our extra savings on packages, free nights, and other discounts, and you know you are in good hands.

Frequently asked questions

Which airlines fly to Waterman?
With airlines providing services to O'Hare Intl. Airport (ORD), a major entry point to Waterman, the choice is yours. Score an awesome deal among these well-known international carriers that fly in and out of this city:

  • United Airlines - 612 flights to Waterman per month
  • American Airlines - 339 flights to Waterman per month
  • Air Canada - 190 flights to Waterman per month

How much is a flight to Waterman?
Last week, prices fluctuated between and for a return fare to Waterman. Fares one-way from () dropped down as low as just during the same period.
How to book the cheapest flight to Waterman?
Using Orbitz, you'll find some of the most incredible flight deals around from a big selection of airlines. But if you'd love to increase your likelihood of nabbing cheap flights to Waterman, here are a few pointers to try out:

  • Depending on your departure point, choose the 'Nearby airports' function (located under the departure and arrival form fields). On occasion, alternative departure points offer cheaper airfares.
  • Similarly, click on the 'Show flexible dates' option to bring up the prices on days either side of your chosen departure. It's possible to pick up cheaper flight deals if you're flexible with your dates.
  • Select 'Show options' to refine your search results. You can choose your preferred airline and seating class here. Under 'Sort & Filter' to the left, you can even select whether you'd like to fly in the morning, afternoon or evening.
  • Book your fare as soon as you've figured out your travel dates. While you can get lucky now and then, airline tickets rarely drop in price as your date of departure nears.
  • Combine your hotels, flights and car rentals into an impressive package deal. Save your hard-earned cash for things you're really excited about, like exploring every corner of Waterman.
  • Flying during peak season means costly airfares. Try to plan your trip outside of popular periods, such as Thanksgiving, New Year's Eve and Easter.

What is the best time to book a flight to Waterman?
On average, the cheapest time to purchase your airfare is in January. This is closely followed by February and August. When looking for a cheap flight to Waterman, make sure you're ready to book. Cheap deals emerge quickly and don't wait around!
What day of the week is the cheapest to book a flight to Waterman?
You can get a great flight deal by making a booking on a Tuesday, Wednesday or Saturday. These are typically the best days to land cheap seats to Waterman.
What is the cheapest day of the week to fly to Waterman?
Look into leaving early in the week to get cheap flights to Waterman. Orbitz data from 2020 indicates Monday is typically the most affordable day to take off, followed by Tuesday. Saturdays were shown to have the most expensive airfares. Presumably, this is because many travelers choose to start their escape when the working week is over.
What is the cheapest month to fly to Waterman?
We won't keep you in suspense — based on Orbitz data, August is generally the cheapest month to fly. Ideal for those who want to sneak in a weekend getaway or just a break from it all before the weather changes. The most expensive time to fly is in the middle of summer, with ticket prices peaking in June.
Which airlines allow free cancellation?
Orbitz makes it a snap to find airlines that offer flexibility. Simply click on "Filter by flexible change policies" when searching for your flights and bingo! You'll see options that include free cancellation within 24 hours of booking, no change fees and of course, the very best price.
What do I need for the flight to Waterman?
There's nothing more exciting than jetting off to a cool new destination, but it's wise to be prepared. These top tips will help get your journey started on the right foot:

  • Your travel documents are the most important things you'll need to take with you on your flight. To avoid any hassles at the time of check-in, make sure that the name on your ticket corresponds with your government-issued photo ID.
  • Make time fly by even faster on your short flight by packing the right things. Think yummy snacks, bottled water and entertainment. If you'd like your journey to Waterman to go quietly, put some noise-canceling headphones or earplugs in your bag too.
  • No matter the weather outside, plane cabins can get chilly. Take a sweater on board to stop the goose bumps.

How do I get cheap first-class/business deals to Waterman?
If you think a first or business-class fare is beyond your reach, you may want to think again. Here are some tips to help you score a premium flight to Waterman for a whole lot less:

  • Be more flexible with your travel dates and hold out for huge sales on first or business-class airfares.
  • Look for a low-cost airline that has business-class seats. They often come with more legroom and a glass of bubbly — and a more affordable price.
  • Make a bid for an upgrade. Some airlines hold online auctions that let you offer a price for a seat at the front of the plane. You may also be able to upgrade with points earned through a flight loyalty program.

What is the best time to go to Waterman?
You'll have loads of fun no matter what time of year you go to Waterman, but June, July and August are the most popular months. Like to pack your schedule with warm-weather adventures? Plan your trip close to June 20. This is when summer starts in the Northern Hemisphere. Expect the mercury to float between 65 ºF and 80 ºF during this time of year.

More to Explore

More to Explore

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.