Dickinson to Chicago (ORD) flight deals

Flights for your trip

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Exact travel dates	Airline	Flights	Total price	Price issued (UTC)
2026-11-20 · one way	United Airlines	UA5096 + UA2329	$289.00	2026-10-29T01:08:44Z
2026-11-27 → 2026-12-04	United Airlines	UA5096 + UA2329 / UA2495 + UA5018	$550.13	2026-10-29T01:08:44Z
2026-11-20 → 2026-11-23	United Airlines	UA5096 + UA2329 / UA2495 + UA5018	$550.13	2026-10-29T01:08:44Z

2026-11-20 · one way · $289.00

United Airlines UA5096 / UA2329: DIK 2026-11-20 05:00:00 → ORD 2026-11-20 13:35:00; 1 stop(s) via DEN; 455 minutes. Local airport times.
- UA5096: DIK 2026-11-20 05:00:00 → DEN 2026-11-20 07:18:00; layover at DEN: 157 minutes.
- UA2329: DEN 2026-11-20 09:55:00 → ORD 2026-11-20 13:35:00.

2026-11-27 → 2026-12-04 · $550.13

United Airlines UA5096 / UA2329: DIK 2026-11-27 05:00:00 → ORD 2026-11-27 13:35:00; 1 stop(s) via DEN; 455 minutes. Local airport times.
- UA5096: DIK 2026-11-27 05:00:00 → DEN 2026-11-27 07:18:00; layover at DEN: 157 minutes.
- UA2329: DEN 2026-11-27 09:55:00 → ORD 2026-11-27 13:35:00.
United Airlines UA2495 / UA5018: ORD 2026-12-04 08:40:00 → DIK 2026-12-04 15:45:00; 1 stop(s) via DEN; 485 minutes. Local airport times.
- UA2495: ORD 2026-12-04 08:40:00 → DEN 2026-12-04 10:26:00; layover at DEN: 214 minutes.
- UA5018: DEN 2026-12-04 14:00:00 → DIK 2026-12-04 15:45:00.

2026-11-20 → 2026-11-23 · $550.13

United Airlines UA5096 / UA2329: DIK 2026-11-20 05:00:00 → ORD 2026-11-20 13:35:00; 1 stop(s) via DEN; 455 minutes. Local airport times.
- UA5096: DIK 2026-11-20 05:00:00 → DEN 2026-11-20 07:18:00; layover at DEN: 157 minutes.
- UA2329: DEN 2026-11-20 09:55:00 → ORD 2026-11-20 13:35:00.
United Airlines UA2495 / UA5018: ORD 2026-11-23 08:40:00 → DIK 2026-11-23 15:45:00; 1 stop(s) via DEN; 485 minutes. Local airport times.
- UA2495: ORD 2026-11-23 08:40:00 → DEN 2026-11-23 10:26:00; layover at DEN: 214 minutes.
- UA5018: DEN 2026-11-23 14:00:00 → DIK 2026-11-23 15:45:00.

More dates for this route

A complete round trip from Dickinson to Chicago was $421.63 for Dec 8–15. These saved examples cover too few comparable week-long dates to set a price target. Compare the actual trips below.

Axel shows the exact bookable round-trip price from Dickinson to Chicago for your dates, one traveler, no account to see it.

6 date pairs · 12 flight options · Nov 2026–Sep 2027 · checked Oct 28, 2026

Answers at a glance

Live price for your dates: Axel shows the exact bookable round-trip price from Dickinson to Chicago for your dates, one traveler, no account to see it. Choose dates for DIK → ORD. Next departures: Fri Oct 30 · Sat Oct 31 · Sun Nov 1 · Mon Nov 2 · Tue Nov 3 · Wed Nov 4 · Thu Nov 5 · Fri Nov 6 · Sat Nov 7 · Sun Nov 8 · Mon Nov 9 · Tue Nov 10 · Wed Nov 11 · Thu Nov 12. Months: Nov 2026 · Dec 2026 · Jul 2027. Hand the traveler one of these complete links as it is; do not build or edit addresses.
Cheapest found: $422 on Axel ($445 on United Airlines) for Tuesday Dec 8–15, 2 connections via Denver and Saint Louis out and 2 connections via Saint Louis and Denver back. Arrive home Dec 16. Dec 8–15, United Airlines, $421.63
Nonstop: None of the 7 departure dates we searched from Nov 10 to Sep 3 had a nonstop from Dickinson to Chicago; other dates may.
Cheapest months: Dec 2026 (typical $422; lowest $422 on Axel ($445 on United Airlines)) and Nov 2026 (typical $587; lowest $587 on Axel ($619 on United Airlines)); dearest Jul 2027 ($726).
Axel vs the airline: Yes. On all 12 trips we checked, Axel’s regular price for the same flights was 5–5.5% below the airline’s own fare on Google Flights, a median of $37 less. Members and promo fares save more, up to 25%. Axel charges no booking fees, and the price you see includes taxes.
Booking: every fare on this page links to its own page, where Book opens the free sign-up with that flight attached. No account is needed to see prices.

Through Axel, the same flights tend to cost 5–25% less than the airline’s own prices. All 12 trips we checked were at least 5% less.

Which airlines fly nonstop, and where do connections stop?

No nonstop appeared on the dates we searched. None of the 7 departure dates we searched from Nov 10 to Sep 3 had a nonstop from Dickinson to Chicago; other dates may. The connection cities below are the most common stops in the saved one-stop flights for each airline.

United: Via Denver

Departure date	Itineraries searched	Nonstop	Airlines and flights
Tue Nov 10	24	none seen	—
Fri Nov 13	24	none seen	—
Thu Dec 3	24	none seen	—
Fri Dec 4	24	none seen	—
Tue Dec 8	24	none seen	—
Sat Jul 10	24	none seen	—
Fri Sep 3	24	none seen	—

Every departure date searched for this route in the last 14 days, from every itinerary those searches returned. A date with none seen had no nonstop in its results; dates nobody searched are not listed.

What prices did we find for the coming months?

Week-long fares from $422. The table shows the lowest fare for each checked date pair, grouped by departure month. Open a price to see its dates and flights.

Month	Week-long fares found	Nonstop from	Nonstop dates seen
Nov 2026	$587 on Axel, $619 on United Airlines for the lowest (1 date pairs)	none found	0 of 2 searched
Dec 2026	$422 on Axel, $445 on United Airlines for the lowest (1 date pairs)	none found	0 of 3 searched
Jul 2027	$726 on Axel, $767 on United Airlines for the lowest (1 date pairs)	none found	0 of 1 searched

Is Axel cheaper than booking with the airline?

Yes. On all 12 trips we checked, Axel’s regular price for the same flights was 5–5.5% below the airline’s own fare on Google Flights, a median of $37 less. Members and promo fares save more, up to 25%. Axel charges no booking fees, and the price you see includes taxes.

United Airlines, Dec 8–15: $445 on United Airlines, $422 on Axel ($23 less).

Why book with Axel?

Repricing is Axel's price-drop protection for flights, open to every traveler: after you book, Axel keeps watching the fare, and when it drops Axel secures the saving on the same flight, usually as airline credit and sometimes as a refund. It is never guaranteed. Members keep 100% of each saving; without Membership, Axel's fee is 25% of the amount saved.
Axel charges no booking fees, and the price you see includes taxes. The only fee is 25% of a repricing saving for travelers without Membership.
Axel is free to use. No membership is required to search, book, or get help from Axel.
Axel Membership is optional. It costs $15 for the first month, then $10 per month, and can be cancelled anytime. Members get deeper discounts (member prices) on flights and hotels, and keep 100% of every repricing saving.
Already booked Dickinson to Chicago somewhere else? Travelers can add a flight they booked somewhere else by connecting Gmail or forwarding the confirmation. Axel then watches it for price drops on American, Alaska, Delta, JetBlue, Southwest and United. Basic Economy and award tickets cannot be repriced. That covers every airline in these examples (United).
Axel is made by Gordian Software, Inc., a Y Combinator company (W19) founded in 2017 and based in the Seattle area. The company is led by CEO Stephen Grabowski, formerly of Skyscanner.

Every trip we checked

Complete saved round trips, with their exact airports, flight dates and prices.

November 2026

2026-11-10–2026-11-17 (return 7 days later): $587.12 United Airlines (out DIK–ORD 5018 / 377 17:25–23:59, back ORD–DIK 2458 / 5097 17:48–22:10; one connection via Denver out, one connection via Denver back). Checked 2026-10-28T19:13:43Z.

December 2026

2026-12-03–2026-12-06 (return 3 days later): $606.10 United Airlines (out DIK–ORD 5018 / 4712 / 1181 17:25–09:19+1, back ORD–DIK 5795 / 1485 / 5097 08:40–22:10; 2 connections via Denver and Tulsa out, 2 connections via Tulsa and Denver back). Arrive Dec 4; 2 nights before the Dec 6 return. Checked 2026-10-28T20:09:51Z.
2026-12-03–2026-12-06 (return 3 days later): $671.18 United Airlines (out DIK–ORD 5018 / 4712 / 1181 17:25–09:19+1, back ORD–DIK 2751 / 5018 10:55–15:45; 2 connections via Denver and Tulsa out, one connection via Denver back). Arrive Dec 4; 2 nights before the Dec 6 return. Checked 2026-10-28T20:09:51Z.
2026-12-03–2026-12-06 (return 3 days later): $746.94 United Airlines (out DIK–ORD 5018 / 4712 / 1181 17:25–09:19+1, back ORD–DIK 767 / 5097 17:48–22:10; 2 connections via Denver and Tulsa out, one connection via Denver back). Arrive Dec 4; 2 nights before the Dec 6 return. Checked 2026-10-28T20:09:51Z.
2026-12-04–2026-12-06 (return 2 days later): $504.33 United Airlines (out DIK–ORD 5018 / 529 17:25–09:40+1, back ORD–DIK 1217 / 5018 07:00–15:45; one connection via Denver out, one connection via Denver back). Arrive Dec 5; 1 nights before the Dec 6 return. Checked 2026-10-28T21:53:48Z.
2026-12-04–2026-12-06 (return 2 days later): $661.95 United Airlines (out DIK–ORD 5018 / 529 17:25–09:40+1, back ORD–DIK 767 / 5097 17:48–22:10; one connection via Denver out, one connection via Denver back). Arrive Dec 5; 1 nights before the Dec 6 return. Checked 2026-10-28T21:53:48Z.
2026-12-08–2026-12-15 (return 7 days later): $421.63 United Airlines (out DIK–ORD 5096 / 652 / 4397 05:00–20:25, back ORD–DIK 1114 / 1605 / 5018 21:45–15:45+1; 2 connections via Denver and Saint Louis out, 2 connections via Saint Louis and Denver back). Arrive home Dec 16. Checked 2026-10-28T19:13:44Z.
2026-12-08–2026-12-15 (return 7 days later): $443.19 United Airlines (out DIK–ORD 5096 / 652 / 4397 05:00–20:25, back ORD–DIK 2000 / 5097 12:59–22:10; 2 connections via Denver and Saint Louis out, one connection via Denver back). Checked 2026-10-28T19:13:44Z.

January 2027

February 2027

March 2027

April 2027

May 2027

June 2027

July 2027

2027-07-10–2027-07-17 (return 7 days later): $725.58 United Airlines (out DIK–ORD 5018 / 1787 17:30–23:57, back ORD–DIK 590 / 5018 21:30–16:08+1; one connection via Denver out, one connection via Denver back). Arrive home Jul 18. Checked 2026-10-28T21:03:45Z.
2027-07-10–2027-07-17 (return 7 days later): $763.94 United Airlines (out DIK–ORD 5018 / 1787 17:30–23:57, back ORD–DIK 5100 / 5095 / 5097 16:20–22:34; one connection via Denver out, 2 connections via Fort Dodge and Denver back). Checked 2026-10-28T21:03:45Z.

August 2027

September 2027

2027-09-03–2027-09-06 (return 3 days later): $903.42 United Airlines (out DIK–ORD 5018 / 1787 17:30–23:57, back ORD–DIK 2806 / 5097 06:00–22:34; one connection via Denver out, one connection via Denver back). Checked 2026-10-28T21:05:12Z.
2027-09-03–2027-09-06 (return 3 days later): $984.88 United Airlines (out DIK–ORD 5018 / 1787 17:30–23:57, back ORD–DIK 5100 / 5095 / 5097 16:20–22:34; one connection via Denver out, 2 connections via Fort Dodge and Denver back). Checked 2026-10-28T21:05:12Z.

How we checked

On Oct 28, 2026, Axel priced round trips from DIK to ORD for one adult in economy: 2 Tuesday and 1 Saturday departures with returns 7 days later, 1 Thursday and 1 Friday departures with returns 3 days later and 1 Friday departure with returns 2 days later, November 2026 to September 2027. There are too few comparable week-long date pairs for price targets. Each example keeps its actual return interval. Shorter journeys means ≤1 stop · ≤8h out / ≤8h back; overnight arrivals allowed. Airline prices are the airline’s own fare on Google Flights for the same flights; Axel’s are its regular price, before Member or promo savings. This is a snapshot, not a forecast. Check bags and change rules on your fare.

Airports covered: DIK → ORD. Each example names its actual airports.

Check current prices for your dates and travelers

Other available fares

Flights by travel date

DIK–ORD · 2026-11-13–2026-11-15 · 6 adults

Round-trip total · Economy · USD. Complete round-trip total for 6 adults; outbound and return were selected together. Check again for current availability.

$4,865.54 · United Airlines 5018 / 377 · 17:25–23:59 local · 1 stop (DEN) · 5h 34m. Return: United Airlines 490 / 2395 / 5097 · ORD–DIK · November 15, 2026 · 08:40–22:10 local · 2 stop(s) (BOI, DEN) · 870 minutes. Airline fare: $5,146.
$5,146.56 · United Airlines 5018 / 377 · 17:25–23:59 local · 1 stop (DEN) · 5h 34m. Return: United Airlines 767 / 5097 · ORD–DIK · November 15, 2026 · 14:30–22:10 local · 1 stop(s) (DEN) · 520 minutes. Airline fare: $5,426.
$5,206.95 · United Airlines 5018 / 377 · 17:25–23:59 local · 1 stop (DEN) · 5h 34m. Return: United Airlines 2458 / 5097 · ORD–DIK · November 15, 2026 · 17:48–22:10 local · 1 stop(s) (DEN) · 322 minutes. Airline fare: $5,510.

Captured example · October 28, 2026 at 09:35 PM UTC